Standard Article

Anion-Assisted Sigmatropic Rearrangements

  1. Stephen R. Wilson

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or043.02

Organic Reactions

Organic Reactions

How to Cite

Wilson, S. R. 2004. Anion-Assisted Sigmatropic Rearrangements. Organic Reactions. 43:2:93–250.

Author Information

  1. New York University, Department of Chemistry, New York, New York

Publication History

  1. Published Online: 15 OCT 2004

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Abstract

The use of sigmatropic rearrangements for the synthesis of organic compounds has become one of the important synthetic tools available to the organic chemist, especially since the development of the detailed stereochemical understanding of these processes in terms of orbital symmetry. The flexibility and predictability of the Cope rearrangement make this type of process widely applicable. The interest and synthetic activity related to the Cope rearrangement can be seen in a previous review of the Claisen and Cope rearrangements. In that review, several variations of the rearrangement were discussed, including examples of the “oxy-Cope” rearrangement. In 1975 examples of an oxy-Cope rearrangement were reported wherein an enormous rate acceleration (1015) was observed on formation of the potassium salt of the oxy-Cope substrate.

This chapter surveys extensions of this type of anionic substituent effect to other [3,3]-, [5,5]-, [1,3]-, and [1,5]-sigmatropic rearrangements as well as retro-[2 + 2] and reverse Diels–Alder reactions. Specifically excluded are the ester enolate Claisen rearrangement which is mechanistically unrelated, the Wittig rearrangement, and the Haller–Bauer reaction. The chemical literature has been searched to the end of 1989. Emphasis is placed on reactions of synthetic utility, novelty, and generality.

Keywords:

  • anion-assisted;
  • sigmatropic rearrangements;
  • mechanism;
  • cycloreversions;
  • sigmatropic shifts;
  • electrocyclic ring opening;
  • side reactions;
  • eliminations;
  • isomerizations;
  • fragmentations;
  • experimental procedures;
  • Cope rearrangements;
  • aromatic bonds;
  • divinylcycloalkanols;
  • vinyl carbinols;
  • vinylcycloalkanols;
  • vinylcyclopropanols;
  • vinylcyclobutanols;
  • potassium hydride;
  • allylcycloalkanols;
  • allyl carbinols;
  • divinylcyclobutanols;
  • scope;
  • limitations

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  1. 1 - 250
Compound Information
Molecular Weight:202.2921
Molecular Formula:C14H18O
InChIKey:UUHIGCUWKAVVIG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:AFKVKMWVOLMZGK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:CALMOZQLFAIYAC-YUSALJHKSA-N
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Compound Information
Molecular Weight:228.3294
Molecular Formula:C16H20O
InChIKey:ZQZIWYLOXRKFAS-PNDOOJTKSA-N
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Compound Information
Molecular Weight:180.2435
Molecular Formula:C11H16O2
InChIKey:QSEGOEOTMKBDLP-AXFHLTTASA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:OTLCVEXOJJXUHH-VAUYPLMASA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:QBNSKQIPELRYSM-WOPDTQHZSA-N
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Compound Information
Molecular Weight:199.4831
Molecular Formula:C6H18KNSi2
InChIKey:IUBQJLUDMLPAGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.3984
Molecular Formula:C18H26O
InChIKey:HMZOHXUWEFASKM-BATUPVCYSA-N
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Compound Information
Molecular Weight:400.5079
Molecular Formula:C24H32O5
InChIKey:RWECUMSHXASASA-RRUPDEEPSA-N
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Compound Information
Molecular Weight:208.2967
Molecular Formula:C13H20O2
InChIKey:PBKPMRJHXVTJOQ-JXMROGBWSA-N
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Compound Information
Molecular Weight:326.5032
Molecular Formula:C17H30O4Si
InChIKey:BWDXYEIIWGCNIQ-SOUVJXGZSA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:OPUNYDBSTNUNMX-QLCUDCOOSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:HXLGVEMUZQNSCF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:KQNCPFSYSWTSAE-JUHZDYGFSA-N
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Compound Information
Molecular Weight:248.3175
Molecular Formula:C15H20O3
InChIKey:IJDIOGOPTOVDAN-ILEOBXNWSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:XWUZDBAHUBPYKN-BDAKNGLRSA-N
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Compound Information
Molecular Weight:180.2435
Molecular Formula:C11H16O2
InChIKey:CXPBKBOUOPGSOP-GWOFURMSSA-N
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Compound Information
Molecular Weight:232.3612
Molecular Formula:C16H24O
InChIKey:GPXKYPSSEWHTSX-IMJJTQAJSA-N
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Compound Information
Molecular Weight:278.3865
Molecular Formula:C17H26O3
InChIKey:OTYJHCVXCSBRAE-TWIWGWFNSA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:ZMVKJNAPENFCDI-XJNFMUPTSA-N
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Compound Information
Molecular Weight:188.2655
Molecular Formula:C13H16O
InChIKey:HGSOHVRZFNALAP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:276.4137
Molecular Formula:C18H28O2
InChIKey:DLKONRCUSIFNNH-YIVQKJEISA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:HQOXFLCKALWJSP-ILXRZTDVSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:HCUVLFUMRZISMV-WMSQIARESA-N
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Compound Information
Molecular Weight:232.3612
Molecular Formula:C16H24O
InChIKey:MLQQGYAJKPQTPB-BPUTZDHNSA-N
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Compound Information
Molecular Weight:296.3618
Molecular Formula:C22H16O
InChIKey:MITDJFRTJMJGDR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3441
Molecular Formula:C16H22O3
InChIKey:JCPONECBPMLMMK-DHYPRVCJSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:BPUQOFKABZACIW-ILGUYDGLSA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:ISMHOYNWDYYSQF-WBTNSWJXSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:PNQIWCQDRIAYKT-RTXFEEFZSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:BAQWRSBSGZULOR-ZFNKZLGSSA-N
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:VZTDCGFDNSNDHE-JMJZKYOTSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:NGDUXHPFTFUXEE-SFYZADRCSA-N
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Compound Information
Molecular Weight:264.4461
Molecular Formula:C18H32O
InChIKey:XVGSRUHAPRWGQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:LDULDLAUBIDAMS-HUUCEWRRSA-N
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Compound Information
Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:RKULNCYHFMBZDO-ILGUYDGLSA-N
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Compound Information
Molecular Weight:173.2316
Molecular Formula:C12H14O
InChIKey:OTNJNFLPQGLZAC-GCHJQGSQSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:OLBLUBVTZQLBKG-FLLCPGJOSA-N
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Compound Information
Molecular Weight:400.5079
Molecular Formula:C24H32O5
InChIKey:UZTNSJIVVNMSDG-BHOLAXHDSA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:BWOSVKFXDJEFEU-FNLUTWJASA-N
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Compound Information
Molecular Weight:253.80894
Molecular Formula:I2
InChIKey:PNDPGZBMCMUPRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:OYGUSHAUMDFKRA-QQRMJSSNSA-N
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Compound Information
Molecular Weight:236.3499
Molecular Formula:C15H24O2
InChIKey:SGCGYFPREKKTSZ-QKGHYUKFSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:ISLGZMXWWHTIJX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:56.1056
Molecular Formula:HKO
InChIKey:KWYUFKZDYYNOTN-UHFFFAOYSA-M
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Compound Information
Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:VWHSPGMDMCQZCP-IRLYEXJDSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:BOYTYWXPJGJXHS-FNORWQNLSA-N
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Compound Information
Molecular Weight:408.713
Molecular Formula:C23H40O2SSi
InChIKey:ZSNCMZBPMDUBRG-FJFXQZEGSA-N
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Compound Information
Molecular Weight:392.671
Molecular Formula:C22H36O2SSi
InChIKey:HVNAVNURCAVKBW-FNEOYEJSSA-N
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Compound Information
Molecular Weight:236.3929
Molecular Formula:C16H28O
InChIKey:OCCKYDKUHWKCGU-DHZHZOJOSA-N
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Compound Information
Molecular Weight:274.4409
Molecular Formula:C19H30O
InChIKey:WAOCQHRUCQKOJP-ITQYTPKQSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:GRGNRQNKCORSMM-CMDGGOBGSA-N
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Compound Information
Molecular Weight:308.4556
Molecular Formula:C19H32O3
InChIKey:MJRNDBQFSAOGJV-ZAIAJBJUSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:OKLHFVPNAHFGDG-GUJYYOPSSA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:UOAHRCQGLQLEQZ-FVFDXKESSA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:GIAUJQTXHJETFP-VXBYDVADSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:MKZGAUMNQFSDKB-OUAUKWLOSA-N
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Compound Information
Molecular Weight:230.3453
Molecular Formula:C16H22O
InChIKey:HQOPFRRZTXXIRQ-XSEXMBABSA-N
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Compound Information
Molecular Weight:250.3334
Molecular Formula:C15H22O3
InChIKey:XGVVMAZRCLHLDO-DHZHZOJOSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:YMNJYDQUEDXSTG-POHAHGRESA-N
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Compound Information
Molecular Weight:326.5032
Molecular Formula:C17H30O4Si
InChIKey:OWQRHFFIXIXEHZ-ZXTLTJADSA-N
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Compound Information
Molecular Weight:276.3707
Molecular Formula:C17H24O3
InChIKey:OSSARTAKWHPEJQ-DMXJWMBRSA-N
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Compound Information
Molecular Weight:232.3612
Molecular Formula:C16H24O
InChIKey:NSJXNEKWYRLARV-NQKGRLOXSA-N
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Compound Information
Molecular Weight:256.3395
Molecular Formula:C17H20O2
InChIKey:LTFXCDIDHVWFNH-QBPKDAKJSA-N
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:WVQNRNBPZPUPSC-UNQZSWDGSA-N
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Compound Information
Molecular Weight:224.2961
Molecular Formula:C13H20O3
InChIKey:BVGCDDKRHQGHPL-GAFUQQFSSA-N
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Compound Information
Molecular Weight:232.3612
Molecular Formula:C16H24O
InChIKey:JFIGVMRLWVIDRN-UGYPUUJKSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:ATUYGTUYELQPKH-ISUQUUIWSA-N
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Compound Information
Molecular Weight:308.4556
Molecular Formula:C19H32O3
InChIKey:YDRJQTIZCMNRLE-BSZOFBHHSA-N
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Compound Information
Molecular Weight:274.4409
Molecular Formula:C19H30O
InChIKey:BIUTYHVEVADIDQ-MNTYIPCHSA-N
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Compound Information
Molecular Weight:276.4137
Molecular Formula:C18H28O2
InChIKey:UFTZBGUGBMLGCF-ORDFZIBCSA-N
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Compound Information
Molecular Weight:218.3346
Molecular Formula:C15H22O
InChIKey:ZZGSQQAWJUTFSQ-SNPRPXQTSA-N
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Compound Information
Molecular Weight:291.467
Molecular Formula:C13H15BrMgO
InChIKey:MSAFBVJAUAXNOA-PASGMERESA-M
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Compound Information
Molecular Weight:262.3441
Molecular Formula:C16H22O3
InChIKey:KRGHZBAEFARSPC-PHPUYBAYSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:PIWVREFZIPEVSA-RTXFEEFZSA-N
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.3175
Molecular Formula:C15H20O3
InChIKey:AKBHZETWWCIMJA-UOGLYNBFSA-N
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Compound Information
Molecular Weight:406.697
Molecular Formula:C23H38O2SSi
InChIKey:MOWMVTRIOYMEMZ-FJFXQZEGSA-N
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Compound Information
Molecular Weight:222.3233
Molecular Formula:C14H22O2
InChIKey:OSSQTCLLTAJIGV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3441
Molecular Formula:C16H22O3
InChIKey:GNCBGZNOESBJQA-UCIIXRRMSA-N
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Compound Information
Molecular Weight:191.2899
Molecular Formula:C13H20O
InChIKey:ISNDXVGTMKDOFV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.3453
Molecular Formula:C16H22O
InChIKey:NRFLTNKQAANPND-ZXLQMTARSA-N
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Compound Information
Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:WDYQNKGZYGQFIE-YSEZFNMTSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:IEUJKHVKLMXFSK-VWYCJHECSA-N
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Compound Information
Molecular Weight:180.2435
Molecular Formula:C11H16O2
InChIKey:KTGMFWFEYWRZTR-YWVKMMECSA-N
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Compound Information
Molecular Weight:230.3453
Molecular Formula:C16H22O
InChIKey:HEJOFDGMWHHMDE-KOZAUXTDSA-N
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Compound Information
Molecular Weight:206.3239
Molecular Formula:C14H22O
InChIKey:HRVUMNUUKILHNW-RFGFWPKPSA-N
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Compound Information
Molecular Weight:238.4411
Molecular Formula:C14H26OSi
InChIKey:NBUFWZGIURVMJJ-UXBLZVDNSA-N
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Compound Information
Molecular Weight:220.3505
Molecular Formula:C15H24O
InChIKey:RESNWHKKMVJDFA-VQIJFOBESA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:QQENJGQETRIVDX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:369.3682
Molecular Formula:C16H36IN
InChIKey:DPKBAXPHAYBPRL-UHFFFAOYSA-M
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:KLXGNPHUVLWLNT-LSSORACZSA-N
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Compound Information
Molecular Weight:222.3233
Molecular Formula:C14H22O2
InChIKey:HNFKXDSQSGFUCK-MJVIPROJSA-N
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Compound Information
Molecular Weight:22.98976928
Molecular Formula:HNa
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:SKXIWXMBLREDMO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3499
Molecular Formula:C15H24O2
InChIKey:NSHDCZWFWZYKMV-JEIKQXNFSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:BQSFGNFQURAPRT-ULOURWJJSA-N
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Compound Information
Molecular Weight:252.415
Molecular Formula:C15H24OS
InChIKey:WPMHBPJNKSIAJE-JEIKQXNFSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:YRAVPVIGAFGHHX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.415
Molecular Formula:C15H24OS
InChIKey:LVTJOWPNMZRUJQ-QKGHYUKFSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:BSZPEODGDZVTJX-RYYBZQDPSA-N
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Compound Information
Molecular Weight:272.425
Molecular Formula:C19H28O
InChIKey:GUBLNUTZKUCVQF-ADBQEYGVSA-N
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Compound Information
Molecular Weight:139.2804
Molecular Formula:C6H14KN
InChIKey:ZMJJCODMIXQWCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3871
Molecular Formula:C17H26O2
InChIKey:LZMQUFWNPUPLQZ-RACIWXJFSA-N
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Compound Information
Molecular Weight:194.2701
Molecular Formula:C12H18O2
InChIKey:LROREIDVWSCICH-WYUUTHIRSA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:PTELMIZRIUWSKW-HHHJXDIYSA-N
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Compound Information
Molecular Weight:256.3395
Molecular Formula:C17H20O2
InChIKey:LUPJOGGZJQNPQA-UAGQMJEPSA-N
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Compound Information
Molecular Weight:218.2915
Molecular Formula:C14H18O2
InChIKey:IYVDWLAYEJKLER-HJWRWDBZSA-N
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Compound Information
Molecular Weight:408.713
Molecular Formula:C23H40O2SSi
InChIKey:OCMSPTJCVHQUCK-CGMSAPAJSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:HGRMQEVOJXQOSR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:HTTJUVQVWOWYIE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:ZQWMYRUDTYWHDH-APLJLPPQSA-N
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Compound Information
Molecular Weight:272.425
Molecular Formula:C19H28O
InChIKey:ZWHLEGWAUUXGCM-PVTMFURFSA-N
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Compound Information
Molecular Weight:180.2435
Molecular Formula:C11H16O2
InChIKey:RSCGJKJZBVLSRA-IUCAKERBSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:ROERSHAWGRIACM-XVNBXDOJSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:UTDBSBPPLXXNKJ-SYMNZTDFSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:NIPZYUUBWYFYNX-NVQVXASISA-N
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Compound Information
Molecular Weight:228.3294
Molecular Formula:C16H20O
InChIKey:FTXIMNYWHJYZHU-VCAJIPCSSA-N
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Compound Information
Molecular Weight:264.4461
Molecular Formula:C18H32O
InChIKey:GPKOELHGWYSCIQ-NTMALXAHSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:FPEVLKMAVLURTN-AEKWLRTRSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:AWGPRVZXOYOASQ-SCVMZPAESA-N
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Compound Information
Molecular Weight:262.3871
Molecular Formula:C17H26O2
InChIKey:HECAUUUTUZTYJX-FIYVZCSKSA-N
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Compound Information
Molecular Weight:208.2967
Molecular Formula:C13H20O2
InChIKey:FVVIOCNWBDVHHU-GMKTYKIGSA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:XSHUZQFITGQABD-PJYWTSEFSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:SHJLFJKVKQUTGU-ULCALQBOSA-N
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Compound Information
Molecular Weight:392.671
Molecular Formula:C22H36O2SSi
InChIKey:LXCIAUHLVRNIGJ-KNSQFYNJSA-N
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Compound Information
Molecular Weight:250.3334
Molecular Formula:C15H22O3
InChIKey:NLEDZOUIOBCZRU-GJZGRUSLSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:QLJSOWWROKWDCC-CLYMUGMRSA-N
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Compound Information
Molecular Weight:260.4143
Molecular Formula:C18H28O
InChIKey:AEZDXDUWJRBVNF-JFIYKMOQSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:RQDDFJKDENCJQF-VBQGMPSSSA-N
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Compound Information
Molecular Weight:305.493
Molecular Formula:C14H17BrMgO
InChIKey:BFHBOWJCCKIUKD-JMYRMHIVSA-M
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Compound Information
Molecular Weight:260.4143
Molecular Formula:C18H28O
InChIKey:QQYLAVSHZYWEGZ-KYHPRHEASA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:YXNYUHBOSCKZQQ-MWLCHTKSSA-N
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Compound Information
Molecular Weight:236.3929
Molecular Formula:C16H28O
InChIKey:VDPFKCFHHHZPOK-FMIVXFBMSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:ROOACYUMUWUEII-VXGBXAGGSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:406.697
Molecular Formula:C23H38O2SSi
InChIKey:VVIADRYCKHLECZ-CGMSAPAJSA-N
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Compound Information
Molecular Weight:194.2701
Molecular Formula:C12H18O2
InChIKey:HHTWTYOQMCDGML-CATGTTOSSA-N
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Compound Information
Molecular Weight:224.2961
Molecular Formula:C13H20O3
InChIKey:CQEZAGNUFTVBDW-LYIQGSDWSA-N
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Compound Information
Molecular Weight:206.3239
Molecular Formula:C14H22O
InChIKey:MUAFXMAZRMFQED-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:CPVZTUSHOMAJCO-GQCTYLIASA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:XFCNNIPRLSOGTQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2921
Molecular Formula:C14H18O
InChIKey:JLRGHUGOXLVCIP-RFHZTLPTSA-N
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Compound Information
Molecular Weight:320.4663
Molecular Formula:C20H32O3
InChIKey:HJNHYQNTOJOGAO-ZYXYNJNDSA-N
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Compound Information
Molecular Weight:314.3771
Molecular Formula:C22H18O2
InChIKey:YHONUOROJSZLHH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:FMGAMGRVRDTKKW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:OQSCKYXJIJSAKV-IQJOONFLSA-N
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Compound Information
Molecular Weight:222.3233
Molecular Formula:C14H22O2
InChIKey:CRQODPNHKWLSEP-ILMHWDKJSA-N
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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:220.3505
Molecular Formula:C15H24O
InChIKey:NNOLUGCIYXQBPX-CABCVRRESA-N
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Compound Information
Molecular Weight:39.0983
Molecular Formula:HK
InChIKey:NTTOTNSKUYCDAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3441
Molecular Formula:C16H22O3
InChIKey:CGQZQKALHFKUDH-SYLANZEVSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:YZIBFCLJXJRCHE-DJLDLDEBSA-N
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Compound Information
Molecular Weight:196.2429
Molecular Formula:C11H16O3
InChIKey:DVNWGCRQBHGUSS-KXUCPTDWSA-N
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Compound Information
Molecular Weight:196.2429
Molecular Formula:C11H16O3
InChIKey:MVVUZUCZZCYTOO-WPRPVWTQSA-N
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Compound Information
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:IRLYMCMDDLLASJ-OINDSLJFSA-N
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Compound Information
Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:ZWPPXSZMFABOGP-JLLWLGSASA-N
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Compound Information
Molecular Weight:222.3233
Molecular Formula:C14H22O2
InChIKey:SMSRMZZYIORPCU-WSWPAOCJSA-N
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Compound Information
Molecular Weight:260.4143
Molecular Formula:C18H28O
InChIKey:OXCWHXZIGSUSEX-KVAFIAHFSA-N
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Compound Information
Molecular Weight:320.4663
Molecular Formula:C20H32O3
InChIKey:NFKNCPQQUJUSKJ-GZTDVGIVSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:HMJADTYGRGHZOW-KCYZZUKISA-N
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Compound Information
Molecular Weight:258.3984
Molecular Formula:C18H26O
InChIKey:DJVFKQWZYNXSMI-YFHUEUNASA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:DUEWXZPFWPWAQL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.3346
Molecular Formula:C15H22O
InChIKey:FLPSATVHZSOBJX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.3865
Molecular Formula:C17H26O3
InChIKey:PEQJRYNTOIZBJQ-LQDABMTFSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:XIWAUCKCLMLJRU-YMBWGVAGSA-N
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Compound Information
Molecular Weight:218.2915
Molecular Formula:C14H18O2
InChIKey:KQMDIXJKQJZWPL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2548
Molecular Formula:C12H16O
InChIKey:AXCRKQQWNSYSSU-HOSYDEDBSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:RKLAOPHXEBUYNH-YHYXMXQVSA-N
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Compound Information
Molecular Weight:208.2967
Molecular Formula:C13H20O2
InChIKey:DXYXHMJAUAMNHZ-STQMWFEESA-N
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Compound Information
Molecular Weight:260.4143
Molecular Formula:C18H28O
InChIKey:NMBALNDLDDDSFM-DTLNGAGPSA-N
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Compound Information
Molecular Weight:276.3707
Molecular Formula:C17H24O3
InChIKey:FKYOKHPNGZYGKZ-FVWJBRROSA-N
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Compound Information
Molecular Weight:194.2701
Molecular Formula:C12H18O2
InChIKey:SYDYKPYGIQLGKO-QYNFOATHSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:XTHFKEDIFFGKHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:HMJADTYGRGHZOW-LJIGWXMPSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:OLBLUBVTZQLBKG-MFTCSFQLSA-N
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Compound Information
Molecular Weight:258.3984
Molecular Formula:C18H26O
InChIKey:DJVFKQWZYNXSMI-LISAXSMJSA-N
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Compound Information
Molecular Weight:258.3984
Molecular Formula:C18H26O
InChIKey:HMZOHXUWEFASKM-QXFOYJGVSA-N
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Compound Information
Molecular Weight:276.4137
Molecular Formula:C18H28O2
InChIKey:UFTZBGUGBMLGCF-DXWTWGPWSA-N
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Compound Information
Molecular Weight:276.4137
Molecular Formula:C18H28O2
InChIKey:UFTZBGUGBMLGCF-ZNFSNMQZSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:BQSFGNFQURAPRT-KKOUDINFSA-N
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Compound Information
Molecular Weight:276.4137
Molecular Formula:C18H28O2
InChIKey:UFTZBGUGBMLGCF-UJHHCITNSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:RUURVXQRDYBLEQ-IVZWLZJFSA-N
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Compound Information
Molecular Weight:22.98976928
Molecular Formula:Na
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:WYVGWCIMNYODGI-GISOBZBCSA-N
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Compound Information
Molecular Weight:232.3612
Molecular Formula:C16H24O
InChIKey:JFIGVMRLWVIDRN-WAQDHOJFSA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:OYGUSHAUMDFKRA-IEFXSWIRSA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:UOAHRCQGLQLEQZ-XIBHJBKLSA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:OYGUSHAUMDFKRA-NTLFTYKBSA-N
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Compound Information
Molecular Weight:234.334
Molecular Formula:C15H22O2
InChIKey:OYGUSHAUMDFKRA-YUMGDKJSSA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:OPUNYDBSTNUNMX-PPWIUVOISA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:GIAUJQTXHJETFP-SGPRVEJOSA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:GIAUJQTXHJETFP-IEVPEVIQSA-N
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Compound Information
Molecular Weight:262.3871
Molecular Formula:C17H26O2
InChIKey:LZMQUFWNPUPLQZ-HMURIODOSA-N
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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:PIHWYPOXHADGHQ-UGZLKAOKSA-N
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Compound Information
Molecular Weight:188.2655
Molecular Formula:C13H16O
InChIKey:UGHFAZNKPOHQHB-BLRKLRJFSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:GBOVQHJMJSFFBD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:241.393
Molecular Formula:C12H18OS2
InChIKey:XAYXRAJRDIEGNJ-QHHAFSJGSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:XAXNLRVNOMFHRT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.261
Molecular Formula:C8H14OS
InChIKey:OQHMDRFKYWOLDH-FNORWQNLSA-N
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Compound Information
Molecular Weight:227.322
Molecular Formula:C16H20O
InChIKey:GIKKEHLAQRTRPH-FOKWVUOFSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:ZZDFHSGCTFRETH-NXEZZACHSA-N
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Compound Information
Molecular Weight:250.3764
Molecular Formula:C16H26O2
InChIKey:RJPARTKSJPTSAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:WYWHAMLLURDLOB-XVNBXDOJSA-N
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Compound Information
Molecular Weight:241.3486
Molecular Formula:C17H22O
InChIKey:VZICCSZGQAAICJ-VXAYPABSSA-N
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Compound Information
Molecular Weight:305.479
Molecular Formula:C17H22OS2
InChIKey:GGPSWEIIBZHJKE-BOXZVXIZSA-N
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Compound Information
Molecular Weight:296.5633
Molecular Formula:C18H36OSi
InChIKey:OCEIQVQDQPGHRC-NTCAYCPXSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:BPWCJFOXPPPMHA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:GOUYDOSRPWBACJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:FPRAIVLZVBOGPD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:336.555
Molecular Formula:C19H28OS2
InChIKey:DHQJAWDOGPXZNT-OLMNPRSZSA-N
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Compound Information
Molecular Weight:260.4467
Molecular Formula:C16H24OSi
InChIKey:UCPQMMXQWFPBQY-JLHYYAGUSA-N
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Compound Information
Molecular Weight:168.2759
Molecular Formula:C11H20O
InChIKey:TUFMCCZFLRAHSL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.2808
Molecular Formula:C13H18O2
InChIKey:KMNYUSMEWNORJA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.3663
Molecular Formula:C15H26O
InChIKey:RSLTVQQROJUNCD-FNORWQNLSA-N
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Compound Information
Molecular Weight:205.297
Molecular Formula:C12H14OS
InChIKey:QNXFXEOTNJWQTO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:20.00634
Molecular Formula:FH
InChIKey:KRHYYFGTRYWZRS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:439.6505
Molecular Formula:C29H44O3
InChIKey:LOLZTYBDHDPKSI-OVPFUJMQSA-N
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Compound Information
Molecular Weight:278.3435
Molecular Formula:C16H22O4
InChIKey:FGRKGZURMFGYIP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:191.52
Molecular Formula:C6H5ClSe
InChIKey:WJCXADMLESSGRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:FMCHGBFGIKQNCT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.2581
Molecular Formula:C13H16O
InChIKey:HXIWJSFMQHKNDK-KIJLLGNVSA-N
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Compound Information
Molecular Weight:234.377
Molecular Formula:C16H26O
InChIKey:PGASPJVLRYSNRF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:336.555
Molecular Formula:C19H28OS2
InChIKey:WXQNYYROZKIXOU-ZIWPVQDUSA-N
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Compound Information
Molecular Weight:194.3132
Molecular Formula:C13H22O
InChIKey:JQISTDDBQXAJFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:294.3444
Molecular Formula:C19H18O3
InChIKey:IYQJLDNIHVIPBC-HMYPBVIVSA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:XZMUELLAFJRFQN-IBCFLCEFSA-N
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Compound Information
Molecular Weight:244.3719
Molecular Formula:C17H24O
InChIKey:GWGLVLDNJNROQB-SKWWLWPPSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:GKBVWPUPBCFIJC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:276.3707
Molecular Formula:C17H24O3
InChIKey:BRJZQUUCXXALPK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:GRCHKEXIRYXLNJ-CHWSQXEVSA-N
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Compound Information
Molecular Weight:242.356
Molecular Formula:C17H22O
InChIKey:CFAMDDWXPVREDL-RWIVAGEPSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:QBRXKYIXJOADEC-AATRIKPKSA-N
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Compound Information
Molecular Weight:220.3505
Molecular Formula:C15H24O
InChIKey:ICDCKVLGYQAPPI-BIZFVBGRSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:UIQVFDMOJUFFEG-NWDGAFQWSA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:ISMHOYNWDYYSQF-PNBKFKSVSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:GBOVQHJMJSFFBD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:YOMWMUYNRRPMGP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:TULFJNGGQMKENG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.3074
Molecular Formula:C14H20O2
InChIKey:QMPJVGNVEYXATR-LNUXAPHWSA-N
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Compound Information
Molecular Weight:433.44
Molecular Formula:C23H30O3Se
InChIKey:XMOLSXJMHZXDLA-GZBGJIERSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:IJPJZRXQOUFBKD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:DCPPYORCTXFEPJ-FNORWQNLSA-N
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Compound Information
Molecular Weight:194.3132
Molecular Formula:C13H22O
InChIKey:ALDJLMSQAKOWPF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:243.3645
Molecular Formula:C17H24O
InChIKey:RXQQLYFKQXUQPU-MMADZMRASA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:HMIYQOJLTGHUJE-NEPJUHHUSA-N
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Compound Information
Molecular Weight:182.2594
Molecular Formula:C11H18O2
InChIKey:GCCMDDFTLCDFQF-XBXARRHUSA-N
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