Standard Article

Tin(II) Enolates in the Aldol, Michael, and Related Reactions

  1. Teruaki Mukaiyama,
  2. Shū Kobayashi

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or046.01

Organic Reactions

Organic Reactions

How to Cite

Mukaiyama, T. and Kobayashi, S. 2004. Tin(II) Enolates in the Aldol, Michael, and Related Reactions. Organic Reactions. 46:1:1–103.

Author Information

  1. Science University of Tokyo, Kagurazaka, Shinjuku-ku, Tokyo, Japan

Publication History

  1. Published Online: 15 OCT 2004

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Abstract

The element tin has played an increasingly important role in organic chemistry as well as organometallic chemistry, serving as a source of new reagents for selective transformations. The main activity in these fields has been focused for a long time on tin(IV) compounds, and tin(II) compounds have been used primarily as reductants of aromatic nitro compounds to aromatic amines.

During the last decade, generation and reactions of various metal enolates have been extensively studied, and successful applications to the controlled formation of carbon–carbon bonds have been realized under mild conditions. The chemistry of tin(IV) enolates has also been studied and several interesting features of these enolates have been reported, whereas tin(II) analogs were relatively unknown in synthetic organic chemistry, probably because of the lack of general methods for generating them.

In 1979, tin(II) fluoride was employed as a reductant of several α-halocarbonyl compounds and allylic halides to generate tin(IV) species, which subsequently reacted with aldehydes to form new carbon–carbon bonds. When metallic tin was used instead of tin(II) fluoride, similar reactions proceeded smoothly. Because the reducing ability of metallic tin is superior to that of tin(II) fluoride, allyl bromide and α-bromoesters, which could not be reduced by tin(II) fluoride, were easily reduced by metallic tin to generate tin(II) enolates, which in turn reacted with aldehydes to yield homoallyl alcohols or β-hydroxyesters. The latter reaction was the first example of the reaction of tin(II) enolates. More conveniently, tin(II) enolates could be generated directly from ketones by using tin(II) triflate and a tertiary amine under neutral conditions.

While strongly basic conditions are required to prepare lithium enolates, tin(II) enolates can be generated under extremely mild conditions. Tin(II) enolates can behave as interesting chemical species in synthetic reactions that cannot be realized with other metal enolates. One of the characteristic features of tin(II) enolate mediated reactions is a highly enantioselective version employing chiral diamines.

Recent developments in the field of stereoselective aldol reactions have resulted in exploitation of the asymmetric version of this reaction, and several successful methods have been reported using chiral carbonyl compounds and/or chiral enolates. However, the efficiency of these reactions is greatly diminished by the tedious procedures for attachment and removal of the chiral auxiliaries. Thus development of a highly enantioselective aldol reaction between two achiral carbonyl compounds utilizing chiral chelating agents became desirable, though the use of chiral addends in the aldol reaction had not met with much success. Chiral diamines derived from (S)-proline, which are postulated to form rigid cis-fused 5-membered bicyclic structures by chelation to a metal center, were found to be effective ligands for several highly enantioselective reactions. Coordination of a chiral diamine to the metal center of the tin(II) enolate effected highly enantioselective cross aldol and Michael reactions between two prochiral reactants.

This review covers the literatures on tin(II) enolates to the middle of 1991.

Keywords:

  • tin enolates;
  • distereoreactions;
  • aldol reactions;
  • Michael reactions;
  • asymmetric reactions;
  • eantioselective reactions;
  • diastreoselective reactions;
  • scope;
  • limitations;
  • sulfnylation;
  • aldol alkylation;
  • achiral substrates;
  • tin powder;
  • tin chloride;
  • tin triflate;
  • experimental procedures

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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:AMIMRNSIRUDHCM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:321.37
Molecular Formula:C11H15NO6S2
InChIKey:APQLCQMKXPJFMV-LLVKDONJSA-N
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Compound Information
Molecular Weight:250.3334
Molecular Formula:C15H22O3
InChIKey:VJATXJLICLTTLP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:Not Available
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Molecular Weight:334.4513
Molecular Formula:C23H26O2
InChIKey:HZAFADQHCDWYGP-RCCQNZRSSA-N
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Molecular Weight:327.462
Molecular Formula:C15H21NO3S2
InChIKey:CPJBVBTYGGYJMB-VXGBXAGGSA-N
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Molecular Weight:250.4
Molecular Formula:C15H22OS
InChIKey:IYLOPAQVPRYIER-WFASDCNBSA-N
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Molecular Weight:278.3865
Molecular Formula:C17H26O3
InChIKey:QJTDKXSKLSFICR-DOTOQJQBSA-N
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Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:YTMHKYDVBYQMHR-PWSUYJOCSA-N
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Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:CLQGBNWSMJQYAF-SWLSCSKDSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:XKGLSKVNOSHTAD-UHFFFAOYSA-N
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Molecular Weight:374.411
Molecular Formula:C18H18N2O5S
InChIKey:IMYDIOZFGCNFTP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.002
Molecular Formula:C4H7BrO
InChIKey:KLTWFFAVGWWIKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:NBBJYMSMWIIQGU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:365.53
Molecular Formula:C20H31NO3S
InChIKey:LLBFKMAUUJNERZ-XIRDDKMYSA-N
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Molecular Weight:393.499
Molecular Formula:C23H23NO3S
InChIKey:UIBPKKMRMLIWOU-UHFFFAOYSA-N
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Molecular Weight:233.351
Molecular Formula:C9H15NO2S2
InChIKey:WULDFFGTOJIUNE-UHFFFAOYSA-N
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Molecular Weight:160.277
Molecular Formula:C8H16OS
InChIKey:BVMZYBZGPGIIQF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:NKWVBPZZQFOVCE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:KWOLFJPFCHCOCG-UHFFFAOYSA-N
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Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:STNJBCKSHOAVAJ-UHFFFAOYSA-N
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Molecular Weight:237.209
Molecular Formula:C8H17BrOSi
InChIKey:HVQJCHUKIFHHSC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:KRIOVPPHQSLHCZ-UHFFFAOYSA-N
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Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:XQDAPPBMJRJOGF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.045
Molecular Formula:C8H7BrO
InChIKey:LIGACIXOYTUXAW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.346
Molecular Formula:C13H18OS
InChIKey:LSVNJRNRBLYRPR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:271.3557
Molecular Formula:C20H17N
InChIKey:Not Available
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Molecular Weight:486.647
Molecular Formula:C25H30N2O4S2
InChIKey:LTFGGECAUOTNOC-RTWAWAEBSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:NFNOAHXEQXMCGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.132
Molecular Formula:C8H6O2
InChIKey:OJUGVDODNPJEEC-UHFFFAOYSA-N
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Molecular Weight:248.3606
Molecular Formula:C16H24O2
InChIKey:ZIVRWIUICNKZNE-GXTWGEPZSA-N
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Molecular Weight:247.377
Molecular Formula:C10H17NO2S2
InChIKey:GNJMXKRVJLBFOC-SFYZADRCSA-N
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Compound Information
Molecular Weight:186.0546
Molecular Formula:C6F6
InChIKey:ZQBFAOFFOQMSGJ-UHFFFAOYSA-N
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Molecular Weight:172.288
Molecular Formula:C9H16OS
InChIKey:ITQKXFVMSDSCHY-UHFFFAOYSA-N
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Molecular Weight:194.1654
Molecular Formula:C7H15O4P
InChIKey:WIJPOUXYFZDYHQ-UHFFFAOYSA-N
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Molecular Weight:353.476
Molecular Formula:C18H27NO4S
InChIKey:WLDKXRDMULONAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:361.478
Molecular Formula:C18H19NO3S2
InChIKey:JFWGOLXTOPMZPC-HUUCEWRRSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:DPCMFIRORYQTCL-NSCUHMNNSA-N
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Molecular Weight:424.577
Molecular Formula:C20H28N2O4S2
InChIKey:RFHWBGIBMLHIGP-GOEBONIOSA-N
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Compound Information
Molecular Weight:383.59
Molecular Formula:C24H33NOS
InChIKey:GOFYEOGQMWTANZ-NQIIRXRSSA-N
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Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:FXLOVSHXALFLKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.3074
Molecular Formula:C14H20O2
InChIKey:LGSVBJRLPYAKQY-JQWIXIFHSA-N
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Compound Information
Molecular Weight:321.3252
Molecular Formula:C16H19NO6
InChIKey:UPNBNAPTXFLGIY-KGYLQXTDSA-N
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Compound Information
Molecular Weight:252.372
Molecular Formula:C14H20O2S
InChIKey:LBHDIVBTIRAPJX-ZYHUDNBSSA-N
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Compound Information
Molecular Weight:206.2378
Molecular Formula:C12H14O3
InChIKey:HNRNEPKUSWJSGX-MNOVXSKESA-N
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Compound Information
Molecular Weight:418.86
Molecular Formula:C2F6O6S2Sn
InChIKey:BYWOMPLPJVZWIO-UHFFFAOYSA-L
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Compound Information
Molecular Weight:187.259
Molecular Formula:C8H13NO2S
InChIKey:RLNUDVDSTWJQIJ-LURJTMIESA-N
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Compound Information
Molecular Weight:220.3074
Molecular Formula:C14H20O2
InChIKey:WVJAKRUBLKBULW-YPMHNXCESA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:QXNRSBTYHRKYBD-SNVBAGLBSA-N
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Compound Information
Molecular Weight:142.1525
Molecular Formula:C7H10O3
InChIKey:KQMCGGGTJKNIMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.2536
Molecular Formula:C12H16O3
InChIKey:ZFGAWRIIHZKSBT-RYUDHWBXSA-N
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Compound Information
Molecular Weight:404.546
Molecular Formula:C20H24N2O3S2
InChIKey:WMWLIRZJFCXZCA-HYMHPKTGSA-N
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Compound Information
Molecular Weight:104.171
Molecular Formula:C4H8OS
InChIKey:RVEBJDGWKWKYBH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:RNDVGJZUHCKENF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:117.213
Molecular Formula:C5H11NS
InChIKey:SLWQSDNKUVNQBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:302.3664
Molecular Formula:C21H18O2
InChIKey:XTDNGCBNJJYEGD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.123
Molecular Formula:C6H14LiN
InChIKey:ZCSHNCUQKCANBX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:119.72
Molecular Formula:H2Sn
InChIKey:KXCAEQNNTZANTK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.286
Molecular Formula:C9H15NO2S
InChIKey:FIEFJRBGCDTCBC-SSDOTTSWSA-N
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Compound Information
Molecular Weight:116.1152
Molecular Formula:C5H8O3
InChIKey:XXRCUYVCPSWGCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:205.253
Molecular Formula:C12H15NO2
InChIKey:VHFZIBNRJPBOBX-YWEFTTLKSA-N
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Compound Information
Molecular Weight:266.399
Molecular Formula:C15H22O2S
InChIKey:QGUXAZZRWCPSHP-OLZOCXBDSA-N
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Compound Information
Molecular Weight:72.0627
Molecular Formula:C3H4O2
InChIKey:AIJULSRZWUXGPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.3181
Molecular Formula:C15H20O2
InChIKey:VMSWCZCIOBEJSU-STQMWFEESA-N
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Compound Information
Molecular Weight:309.447
Molecular Formula:C15H19NO2S2
InChIKey:LVZLBUOHENMPEV-YPMHNXCESA-N
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Compound Information
Molecular Weight:212.3318
Molecular Formula:C12H24N2O
InChIKey:INYLXTDJQYEXAY-RYUDHWBXSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:GXFZWRBRWPHABF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.323
Molecular Formula:C17H18O3
InChIKey:UVNNIFZAVMGXGO-DOTOQJQBSA-N
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Compound Information
Molecular Weight:299.4088
Molecular Formula:C22H21N
InChIKey:WOBATNWWMWHTHE-PTGBLXJZSA-N
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Molecular Weight:280.3609
Molecular Formula:C19H20O2
InChIKey:YPVPPDZCBGJMHW-BUHFOSPRSA-N
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Compound Information
Molecular Weight:270.323
Molecular Formula:C17H18O3
InChIKey:ACGOCZRLBYATQI-PXAZEXFGSA-N
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Compound Information
Molecular Weight:271.376
Molecular Formula:C13H21NO3S
InChIKey:ZSILFAMIPSQQEP-MXWKQRLJSA-N
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Compound Information
Molecular Weight:264.2552
Molecular Formula:C11H21O5P
InChIKey:SKXPDODJFDIFLF-NXEZZACHSA-N
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Compound Information
Molecular Weight:360.4886
Molecular Formula:C25H28O2
InChIKey:YIAHPIGKJWHDBH-LHGMORBZSA-N
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Compound Information
Molecular Weight:238.346
Molecular Formula:C13H18O2S
InChIKey:YKVUEYAWGQZGAP-STQMWFEESA-N
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Compound Information
Molecular Weight:243.097
Molecular Formula:C10H11BrO2
InChIKey:BKTKLDMYHTUESO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:219.324
Molecular Formula:C8H13NO2S2
InChIKey:HKHORKLZNLWHFY-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:246.3447
Molecular Formula:C16H22O2
InChIKey:NRJVDVSUSFNFKR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.21
Molecular Formula:C3H6S2
InChIKey:PFWSEYMNCOMKDX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:132.1592
Molecular Formula:C9H8O
InChIKey:KUIZKZHDMPERHR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.323
Molecular Formula:C17H18O3
InChIKey:UDANXEQSQZYNRE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:279.355
Molecular Formula:C14H17NO3S
InChIKey:BVDJJWITQJUUEZ-GIPNMCIBSA-N
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Compound Information
Molecular Weight:360.4886
Molecular Formula:C25H28O2
InChIKey:OETUWDVVLSQDBN-WKOYBBDISA-N
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Compound Information
Molecular Weight:136.975
Molecular Formula:C3H5BrO
InChIKey:VQFAIAKCILWQPZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:239.2677
Molecular Formula:C12H17NO4
InChIKey:ANUPGHOHZNKSDK-RKDXNWHRSA-N
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Compound Information
Molecular Weight:44.0526
Molecular Formula:C2H4O
InChIKey:IKHGUXGNUITLKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.2134
Molecular Formula:C10H14O8
InChIKey:YEAYWOYDFBOVQW-OIBJUYFYSA-N
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Compound Information
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:AOBSWBDDACZYAY-QWRGUYRKSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:UVRWUYAKBXOLRF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.438
Molecular Formula:C14H20OS2
InChIKey:DVAGHDQMXSOINI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:235.302
Molecular Formula:C12H13NO2S
InChIKey:OTTRITLDQRGFCF-LDYMZIIASA-N
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:FUSUHKVFWTUUBE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:113.2007
Molecular Formula:C7H15N
InChIKey:HTLZVHNRZJPSMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:305.3688
Molecular Formula:C17H23NO4
InChIKey:DPBFKRSGSRJUGL-ZIAGYGMSSA-N
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Compound Information
Molecular Weight:254.3236
Molecular Formula:C17H18O2
InChIKey:CARFBJXITDSGJE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.3969
Molecular Formula:C15H30O3
InChIKey:ZZPTZWUYVAVXOG-GJZGRUSLSA-N
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Compound Information
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:CAXIQKXPSQYDIR-CMDGGOBGSA-N
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Compound Information
Molecular Weight:520.663
Molecular Formula:C28H28N2O4S2
InChIKey:GFQYSQRCEIOSSK-RPBOFIJWSA-N
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Compound Information
Molecular Weight:351.503
Molecular Formula:C19H29NO3S
InChIKey:LZZCJASQMFFVNM-DZKIICNBSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:YQOYJANCWJWEAE-LBPRGKRZSA-N
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Compound Information
Molecular Weight:369.4541
Molecular Formula:C22H27NO4
InChIKey:OHKCSGGSQMZXDD-QMBNUAFSSA-N
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Compound Information
Molecular Weight:274.742
Molecular Formula:C16H15ClO2
InChIKey:YKJJINLOTHGNPP-MEDUHNTESA-N
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Compound Information
Molecular Weight:270.323
Molecular Formula:C17H18O3
InChIKey:RWYUOIPANURTLR-CVEARBPZSA-N
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Compound Information
Molecular Weight:258.3554
Molecular Formula:C17H22O2
InChIKey:XVXUADXTOSLYNM-YRNVUSSQSA-N
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:QSJXEFYPDANLFS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:371.516
Molecular Formula:C20H21NO2S2
InChIKey:SIGQVNKMAQJHDO-MSOLQXFVSA-N
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Compound Information
Molecular Weight:393.499
Molecular Formula:C23H23NO3S
InChIKey:RTGCHFSLWYVWLM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.404
Molecular Formula:C11H19NO2S2
InChIKey:VFHSMPDHANCCQH-SECBINFHSA-N
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Compound Information
Molecular Weight:143.1406
Molecular Formula:C6H9NO3
InChIKey:XXUOGAYBSXZFTD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2581
Molecular Formula:C11H16N2
InChIKey:MCHWKJRTMPIHRA-NSHDSACASA-N
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Compound Information
Molecular Weight:142.1525
Molecular Formula:C7H10O3
InChIKey:LSCFJXBYVYYZTB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:ZPVFWPFBNIEHGJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:399.569
Molecular Formula:C22H25NO2S2
InChIKey:NNAOWEUPBMFEJT-UXHICEINSA-N
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Compound Information
Molecular Weight:333.445
Molecular Formula:C18H23NO3S
InChIKey:HJDIIMSNEJEDTM-SYCAHVKKSA-N
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Compound Information
Molecular Weight:260.3713
Molecular Formula:C17H24O2
InChIKey:UXEUCYRMRVACQE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:398.499
Molecular Formula:C20H18N2O3S2
InChIKey:WJMGRWRNQXSTRQ-YESZJQIVSA-N
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Compound Information
Molecular Weight:302.3664
Molecular Formula:C21H18O2
InChIKey:RTHFGDIIBTXOIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.377
Molecular Formula:C13H12N2O2S2
InChIKey:QMSPJGRJTSKINQ-NSHDSACASA-N
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Compound Information
Molecular Weight:150.1314
Molecular Formula:C8H6O3
InChIKey:JKNKNWJNCOJPLI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:307.431
Molecular Formula:C15H17NO2S2
InChIKey:JZRFSZQBPNWNGV-HOVLTTNMSA-N
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Compound Information
Molecular Weight:336.429
Molecular Formula:C15H16N2O3S2
InChIKey:GXBCZBLAODIUOS-USWWRNFRSA-N
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Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:AKGGYBADQZYZPD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:DBAMUTGXJAWDEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:QTISZPXYPZNBQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.238
Molecular Formula:C9H18O2
InChIKey:BIEQEQORPVLGMS-CBAPKCEASA-N
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Compound Information
Molecular Weight:178.359
Molecular Formula:C8H18S2
InChIKey:CSDLJKZPRZMNKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:372.4117
Molecular Formula:C21H24O6
InChIKey:MRLZCTCDACPBQZ-CTNGQTDRSA-N
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Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:YKFKEYKJGVSEIX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:314.465
Molecular Formula:C18H18OS2
InChIKey:ONFSBBLRXKUXSB-INIZCTEOSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:UNNGUFMVYQJGTD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1849
Molecular Formula:C7H14O2
InChIKey:QSJHFVISBQRPRU-ZETCQYMHSA-N
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Compound Information
Molecular Weight:283.3218
Molecular Formula:C17H17NO3
InChIKey:FVCULXKBOZLKOI-CZUORRHYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:FDPIMTJIUBPUKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:KVFQMAZOBTXCAZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:OIKRFBAPTDCZDO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.3236
Molecular Formula:C17H18O2
InChIKey:DEOOQAQBZGVGIV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.3236
Molecular Formula:C17H18O2
InChIKey:Not Available
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Compound Information
Molecular Weight:129.2432
Molecular Formula:C8H19N
InChIKey:JGFZNNIVVJXRND-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2108
Molecular Formula:C8H16O3
InChIKey:AIUXVDCAPTYWHZ-YUMQZZPRSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:JARKCYVAAOWBJS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.3181
Molecular Formula:C15H20O2
InChIKey:KSWLTWDBKKOLQA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.2705
Molecular Formula:C15H14O2
InChIKey:BQAQAINICPCLQB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.1632
Molecular Formula:C8H10O3
InChIKey:MUTGBJKUEZFXGO-OLQVQODUSA-N
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Compound Information
Molecular Weight:218.2915
Molecular Formula:C14H18O2
InChIKey:QLLQJSUZKVRXRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.358
Molecular Formula:C11H14O2S2
InChIKey:GZRZVAAQODETSC-JTQLQIEISA-N
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Compound Information
Molecular Weight:277.745
Molecular Formula:C12H20ClNO4
InChIKey:YIAKRFHMDORMSE-KXUCPTDWSA-N
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Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:YGCZTXZTJXYWCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:381.529
Molecular Formula:C20H31NO4S
InChIKey:OTUZKEXAJRBFGQ-HYVNUMGLSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:UWMMLVJAFQGRTC-GWCFXTLKSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:BSISGLSTYYYBJI-AATRIKPKSA-N
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Compound Information
Molecular Weight:266.155
Molecular Formula:C8H12BrNO2S
InChIKey:GMUYEGVKPLOFLA-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:108.642
Molecular Formula:C3H9ClSi
InChIKey:IJOOHPMOJXWVHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:VEYGJDLCKIRQQG-NWDGAFQWSA-N
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Compound Information
Molecular Weight:280.53
Molecular Formula:Br2Sn
InChIKey:SRJUSZBTOYQDIR-UHFFFAOYSA-L
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Compound Information
Molecular Weight:264.3154
Molecular Formula:C12H24O6
InChIKey:XEZNGIUYQVAUSS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.238
Molecular Formula:C9H18O2
InChIKey:UQJXEZXTFHQZDX-SECBINFHSA-N
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Compound Information
Molecular Weight:244.3288
Molecular Formula:C16H20O2
InChIKey:SLWMUFAPTXOYKR-YRNVUSSQSA-N
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Compound Information
Molecular Weight:343.331
Molecular Formula:C15H23BrO2Si
InChIKey:HYYWHEYHPPFZIV-OLZOCXBDSA-N
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Compound Information
Molecular Weight:235.2359
Molecular Formula:C12H13NO4
InChIKey:DCKOJAPIBQBDKB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:AVPYQKSLYISFPO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.2705
Molecular Formula:C15H14O2
InChIKey:ZTCFOSQTSRNLHW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.293
Molecular Formula:C11H14O2S
InChIKey:JAASESUWVOZBGV-WPRPVWTQSA-N
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Compound Information
Molecular Weight:42.0367
Molecular Formula:C2H2O
InChIKey:CCGKOQOJPYTBIH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:TUIBUNUGLRAASE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:294.452
Molecular Formula:C17H26O2S
InChIKey:AGHOYEUNXZAQEK-GUYCJALGSA-N
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Compound Information
Molecular Weight:218.356
Molecular Formula:C11H22O2S
InChIKey:YRXHHJZETFHASN-BDAKNGLRSA-N
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Compound Information
Molecular Weight:298.3762
Molecular Formula:C19H22O3
InChIKey:NCBKEBZOXHDXNB-ZWKOTPCHSA-N
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Compound Information
Molecular Weight:136.279
Molecular Formula:C5H12S2
InChIKey:RJQVVQDWHKZIHU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:257.124
Molecular Formula:C11H13BrO2
InChIKey:LFWOAUKEMQHSHE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.3434
Molecular Formula:C16H20N2
InChIKey:XNUJQYGTHGYURE-AWEZNQCLSA-N
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Compound Information
Molecular Weight:144.2114
Molecular Formula:C8H16O2
InChIKey:QDSWKHGIZCQXIT-SSDOTTSWSA-N
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Compound Information
Molecular Weight:249.307
Molecular Formula:C8H11NO4S2
InChIKey:XAWVLLHJDGEBKE-MRVPVSSYSA-N
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Compound Information
Molecular Weight:480.684
Molecular Formula:C24H36N2O4S2
InChIKey:JEWHSAHVLOWIKB-UXHICEINSA-N
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Compound Information
Molecular Weight:371.385
Molecular Formula:C17H27BrO2Si
InChIKey:MZKXAGIPRUXTDU-LSDHHAIUSA-N
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Compound Information
Molecular Weight:256.4241
Molecular Formula:C16H32O2
InChIKey:VEHKSWUVOHLUED-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:PMHWDQUNGAIQRY-GQCTYLIASA-N
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Compound Information
Molecular Weight:195.054
Molecular Formula:C6H11BrO2
InChIKey:XIMFCGSNSKXPBO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.0967
Molecular Formula:FK
InChIKey:NROKBHXJSPEDAR-UHFFFAOYSA-M
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Compound Information
Molecular Weight:146.25
Molecular Formula:C7H14OS
InChIKey:JEGFJPIEPWLJJM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.426
Molecular Formula:C16H24O2S
InChIKey:XBJGNVOHPIOFEV-OCCSQVGLSA-N
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Compound Information
Molecular Weight:250.3334
Molecular Formula:C15H22O3
InChIKey:HWEJQFPGKDHPCE-GJZGRUSLSA-N
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Compound Information
Molecular Weight:296.3603
Molecular Formula:C19H20O3
InChIKey:AUOJKCURQAQKNM-DPYIKZRWSA-N
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Compound Information
Molecular Weight:177.039
Molecular Formula:C6H9BrO
InChIKey:KDXYEWRAWRZXFT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2072
Molecular Formula:C12H10O
InChIKey:JRMSWNFVXQMZJK-WDZFZDKYSA-N
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Compound Information
Molecular Weight:278.143
Molecular Formula:C10H16BrNO3
InChIKey:JWYXIDALNCZSOB-SSDOTTSWSA-N
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Compound Information
Molecular Weight:272.382
Molecular Formula:C18H24O2
InChIKey:RCQDCDSSFOOIDF-XYOKQWHBSA-N
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Compound Information
Molecular Weight:293.381
Molecular Formula:C15H19NO3S
InChIKey:YPZLILQULOOVMY-KGYLQXTDSA-N
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Compound Information
Molecular Weight:322.196
Molecular Formula:C12H20BrNO4
InChIKey:UIFJGKDHHWYYQM-KXUCPTDWSA-N
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Compound Information
Molecular Weight:232.3181
Molecular Formula:C15H20O2
InChIKey:VZQWKPGDKFJCMT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.0728
Molecular Formula:C4H4O3
InChIKey:Not Available
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Compound Information
Molecular Weight:291.771
Molecular Formula:C13H22ClNO4
InChIKey:GUCOFMYKWVZUDB-MXWKQRLJSA-N
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Compound Information
Molecular Weight:344.4462
Molecular Formula:C24H24O2
InChIKey:LKJRWHFSXVOWNW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:OOGVUQMNUBSFQP-RNCFNFMXSA-N
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Compound Information
Molecular Weight:298.2901
Molecular Formula:C17H14O5
InChIKey:WIXUQXJBEXNLOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.384
Molecular Formula:C15H20OS
InChIKey:VXVPJQNMTBCABN-ZFWWWQNUSA-N
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Compound Information
Molecular Weight:313.436
Molecular Formula:C14H19NO3S2
InChIKey:HCYCXQNLTKQLGA-GHMZBOCLSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:HEOVGVNITGAUKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:CICRXRZZEMHKQI-STQMWFEESA-N
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Compound Information
Molecular Weight:214.646
Molecular Formula:C10H11ClO3
InChIKey:CHUORCGHQMNDOK-VHSXEESVSA-N
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Compound Information
Molecular Weight:227.098
Molecular Formula:C10H11BrO
InChIKey:QMOSZSHTSOWPRX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:445.659
Molecular Formula:C29H35NOS
InChIKey:IWZMYJCDGCBFPC-GJZUVCINSA-N
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Compound Information
Molecular Weight:243.323
Molecular Formula:C11H17NO3S
InChIKey:CMLAEEDJJBBCHF-DTWKUNHWSA-N
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Compound Information
Molecular Weight:164.158
Molecular Formula:C9H8O3
InChIKey:YLHXLHGIAMFFBU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:303.396
Molecular Formula:C18H25NO3
InChIKey:NHHKCDUZYYUPDX-ANGDWKNPSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:305.392
Molecular Formula:C16H19NO3S
InChIKey:RJVMBCHETXOQGC-CFYKVZDHSA-N
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Compound Information
Molecular Weight:136.1479
Molecular Formula:C8H8O2
InChIKey:DYSMWEMINDEPKS-NSCUHMNNSA-N
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Compound Information
Molecular Weight:115.034
Molecular Formula:CH4Cl2Si
InChIKey:NWKBSEBOBPHMKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:SYBYTAAJFKOIEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:FWFSEYBSWVRWGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.673
Molecular Formula:C11H13ClO2
InChIKey:LLPTWXIZJSRCQW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.028
Molecular Formula:C5H9BrO2
InChIKey:ARFLASKVLJTEJD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.396
Molecular Formula:C13H16OS2
InChIKey:WMCWJGFMMIEAEC-JTQLQIEISA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:108.0948
Molecular Formula:C6H4O2
InChIKey:AZQWKYJCGOJGHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:247.2897
Molecular Formula:C14H17NO3
InChIKey:STOOUUNOLPMRGC-QWHCGFSZSA-N
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Compound Information
Molecular Weight:212.375
Molecular Formula:C11H16S2
InChIKey:AIIGUIULOLNNLJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:267.367
Molecular Formula:C12H13NO2S2
InChIKey:WBAMXYLHUMHKOT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.3074
Molecular Formula:C14H20O2
InChIKey:JHCKUFDSQRIKRB-SMDDNHRTSA-N
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Compound Information
Molecular Weight:296.4034
Molecular Formula:C20H24O2
InChIKey:XHHIUAVPQYIHJM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:328.468
Molecular Formula:C20H24O2S
InChIKey:FFGZVGFPOQWGJZ-MOPGFXCFSA-N
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Compound Information
Molecular Weight:154.594
Molecular Formula:C8H7ClO
InChIKey:Not Available
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Compound Information
Molecular Weight:273.35
Molecular Formula:C15H15NO2S
InChIKey:ZMRUITBTNJKVEZ-BXUZGUMPSA-N
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Compound Information
Molecular Weight:330.4196
Molecular Formula:C23H22O2
InChIKey:ZZZCMWHJUNQFOZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:285.382
Molecular Formula:C12H15NO3S2
InChIKey:OLDWIGXBUMKWLC-DTWKUNHWSA-N
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Compound Information
Molecular Weight:458.594
Molecular Formula:C23H26N2O4S2
InChIKey:KRCDPZJCYVLWDD-FXAWDEMLSA-N
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Compound Information
Molecular Weight:320.3817
Molecular Formula:C21H20O3
InChIKey:KTGSPORONWSWAG-UXHICEINSA-N
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Compound Information
Molecular Weight:160.1247
Molecular Formula:C6H8O5
InChIKey:QAKBYHGCDUORNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:129.114
Molecular Formula:C5H7NO3
InChIKey:COCHMAAUXSQMED-UHFFFAOYSA-N
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Compound Information
Molecular Weight:331.429
Molecular Formula:C18H21NO3S
InChIKey:FZDAIWYLWBNHNV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.615
Molecular Formula:C2H7ClSi
InChIKey:YGHUUVGIRWMJGE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:215.2032
Molecular Formula:C9H13NO5
InChIKey:XKKSZJGJZNIAJX-LURJTMIESA-N
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Compound Information
Molecular Weight:56.0633
Molecular Formula:C3H4O
InChIKey:UYLUJGRCKKSWHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2906
Molecular Formula:C11H22O3
InChIKey:VQQAYYRVUCGBTQ-MNOVXSKESA-N
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Compound Information
Molecular Weight:282.3768
Molecular Formula:C19H22O2
InChIKey:YEJLPZIZBGAKHT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.383
Molecular Formula:C12H24O2S
InChIKey:LMAICGDHWXZNOR-RKDXNWHRSA-N
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Compound Information
Molecular Weight:188.31
Molecular Formula:C8H12OS2
InChIKey:DSPZIDUUWVPDAW-LURJTMIESA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:SCKMBACBARMBIW-GXFFZTMASA-N
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Compound Information
Molecular Weight:400.3787
Molecular Formula:C21H20O8
InChIKey:RULFHBYNNNGYAO-UTKZUKDTSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.3074
Molecular Formula:C14H20O2
InChIKey:WBDKWGXOOIVFEE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:NTIZESTWPVYFNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.296
Molecular Formula:C13H11NO3S
InChIKey:XJAHYKDHXYQYIH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:414.541
Molecular Formula:C21H22N2O3S2
InChIKey:NSJYIBKHIZTFSX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.2439
Molecular Formula:C14H12O2
InChIKey:VCWCUMTYRJJXHF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:275.431
Molecular Formula:C12H21NO2S2
InChIKey:YKHDQGMKMRLXKG-ZJUUUORDSA-N
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Compound Information
Molecular Weight:86.1323
Molecular Formula:C5H10O
InChIKey:YGHRJJRRZDOVPD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:NUJGJRNETVAIRJ-UHFFFAOYSA-N
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