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Divinylcyclopropane-Cycloheptadiene Rearrangement

  1. Tomáš Hudlicky,
  2. Rulin Fan,
  3. Josephine W. Reed,
  4. Kumar G. Gadamasetti

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or041.01

Organic Reactions

Organic Reactions

How to Cite

Hudlicky, T., Fan, R., Reed, J. W. and Gadamasetti, K. G. 2004. Divinylcyclopropane-Cycloheptadiene Rearrangement. Organic Reactions. 41:1:1–133.

Author Information

  1. Virginia Polytechnic Institute and State University, Department of Chemistry, Blacksburg, Virginia

Publication History

  1. Published Online: 15 OCT 2004

Chemistry Terms

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Abstract

The first documented report of a possible Cope rearrangement was probably that of Baeyer, who prepared eucarvone by hydrobromination of carvone in 1894. Although the transformation was briefly studied at that time, it was not until the 1950s that this and other Cope-type rearrangements received detailed attention. The thermal isomerization of cis-divinylcyclopropane to cycloheptan-1,4-diene was reported by Vogel in 1960 during his studies of the Cope rearrangement of 1,5-hexadienes annulated by a homologous series of carbocyclic rings. Scores of mechanistic studies followed this discovery upon the realization that the rearrangement could be related to the conceptually similar vinylcyclopropane–cyclopentene isomerization discovered a year earlier. It was also recognized that this rearrangement might be operating in the formation of cycloheptatriene from norcaradiene during photolysis of diazomethane in benzene. The topic received considerable attention in the 1960s, an era of mechanistic investigations of various concerted transformations. During the 1970s it enjoyed exploitation in many synthetic strategies, and the following decade the elements of this rearrangement were incorporated into tandem or multistep procedures in a preconceived manner. Many aspects of the various permutations of the Cope rearrangement have been previously reviewed.

The purpose of this review is to summarize the mechanistic, stereochemical, and practical results in this area in the context of the evolution of synthetic achievements during the last 40 years. Also described in this chapter are the transformations of several of the simple heteroatom permutations of this rearrangement in order to render appropriate comparisons of various systems. A discussion addresses those rearrangements of cyclopropanes, oxiranes, thiiranes, and aziridine rings substituted with vicinal vinyl groups. Excluded from this review are rearrangements of those divinylsubstituted three-membered rings that contain more than a single heteroatom within the reacting manifold. Brief mention of these systems along with a guide to the literature is found in the last section of this chapter.

The literature is covered through December 1990. Many of the principal researchers in this field have been contacted and many unpublished transformations have been included in the tables.

Keywords:

  • divinylcyclopropane;
  • cycloheptadiene;
  • rearrangement;
  • mechanism;
  • annulation;
  • natural product synthesis;
  • heterocyclic systems;
  • scope;
  • limitations;
  • divinyloxiranes;
  • divinylaziridines;
  • divinylthiiranes;
  • experimental procedures;
  • Cope rearrangement

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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:JBVCYDCDMVOVHU-KDXUFGMBSA-N
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Compound Information
Molecular Weight:266.313
Molecular Formula:C13H14O4S
InChIKey:FBFZPDRDJJGSBH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:119.378
Molecular Formula:CHCl3
InChIKey:HEDRZPFGACZZDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:UIOVYWVLNBYVTF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:418.4801
Molecular Formula:C23H30O7
InChIKey:PVOYUFOPBPDNEG-QGOAFFKASA-N
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Compound Information
Molecular Weight:176.2548
Molecular Formula:C12H16O
InChIKey:UFXRPRQYZDIBDP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:UDKCHWVGPNQSQK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:QXBZQOORUALIHN-YVNUIETPSA-N
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Compound Information
Molecular Weight:84.1588
Molecular Formula:C2H5KO
InChIKey:RPDAUEIUDPHABB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:167.076
Molecular Formula:C7H12Cl2
InChIKey:OQFLWCPXQFAQLS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:TTYIJTXBBRUWBF-BTJINBLDSA-N
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Compound Information
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:BPTIQXQJYFTNPH-ITAJPAFDSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:XHRNQDMNINGCES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1916
Molecular Formula:C9H12
InChIKey:FIPFXUIWLHAZSB-GLIMQPGKSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:PJZNWOZWRMDBHQ-RNFRBKRXSA-N
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Compound Information
Molecular Weight:254.3975
Molecular Formula:C13H22O3Si
InChIKey:IUPFQDSRUVCORW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:418.4801
Molecular Formula:C23H30O7
InChIKey:TXKLJDRILSQNCU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:LNFQBEVBVGDZOJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.0502
Molecular Formula:C7H9IO
InChIKey:NJQHDRGYCBWCQC-AATRIKPKSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:ZWAZSXPAOONGLS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:312.4458
Molecular Formula:C21H28O2
InChIKey:XBMICEPMNNMHED-PMACEKPBSA-N
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Compound Information
Molecular Weight:78.133
Molecular Formula:C2H6OS
InChIKey:IAZDPXIOMUYVGZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:264.36
Molecular Formula:C16H24O3
InChIKey:CLNKAKROMNBLCO-GIFUCUPESA-N
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Compound Information
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:SESSIVFHGMLSAN-QCLAVDOMSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:QNGQIURXCUHNAT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.9368
Molecular Formula:MnO2
InChIKey:Not Available
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Compound Information
Molecular Weight:72.1488
Molecular Formula:C5H12
InChIKey:OFBQJSOFQDEBGM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.0237
Molecular Formula:C6H7IO
InChIKey:CUXAOFGEUOCFLV-SNAWJCMRSA-N
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Compound Information
Molecular Weight:280.5209
Molecular Formula:C17H32OSi
InChIKey:SKNQRHSNACBACG-JZMJITHDSA-N
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Compound Information
Molecular Weight:150.722
Molecular Formula:C6H15ClSi
InChIKey:BCNZYOJHNLTNEZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:474.6295
Molecular Formula:C28H42O6
InChIKey:SUEPMIIZOTZISD-GYXQUFJGSA-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:128.599
Molecular Formula:C7H9Cl
InChIKey:ISGVVQCCMFESKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.5209
Molecular Formula:C17H32OSi
InChIKey:SZUUYRHKWAVTQE-LUYYIBBOSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:PCTQXTPEUWPMPH-IQPYVPGXSA-N
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Compound Information
Molecular Weight:238.4411
Molecular Formula:C14H26OSi
InChIKey:DWBVJSDEPRKBLG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2447
Molecular Formula:C11H16
InChIKey:KIFXGGYCNMHCSX-DZHRUPLWSA-N
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Compound Information
Molecular Weight:74.05
Molecular Formula:C5H7Li
InChIKey:QYQIXRCPWXQOLR-JEDNCBNOSA-N
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Compound Information
Molecular Weight:242.3129
Molecular Formula:C16H18O2
InChIKey:ISTCRQOHJAMIAH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:145.201
Molecular Formula:C10H11N
InChIKey:XPMDMAYKUNIXSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:UCYPWSYSMRULKS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:242.3129
Molecular Formula:C16H18O2
InChIKey:ZTXORHNDWNHLMJ-BNQVXVOMSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:UEYYOGFVPAORCH-RNFRBKRXSA-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:94.1543
Molecular Formula:C7H10
InChIKey:ISSYTHPTTMFJKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:GMLIBUROLFLGMY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.1943
Molecular Formula:C8H12N2
InChIKey:ZGXVXLPQFOBPMW-HWKANZROSA-N
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Compound Information
Molecular Weight:224.4146
Molecular Formula:C13H24OSi
InChIKey:UXGQIQCCFBCNKT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2606
Molecular Formula:C11H18
InChIKey:IRKYSUMPMNRVDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:189.05
Molecular Formula:C7H9BrO
InChIKey:LMSGKIBQYMRIQJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:APDZRJZYGWLSEF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.705
Molecular Formula:C10H14CuLi
InChIKey:XYXPFXNDFKSGGK-IOHDCEMHSA-N
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Compound Information
Molecular Weight:182.2164
Molecular Formula:C10H14O3
InChIKey:BYYHWIOZPCWFRG-UITAMQMPSA-N
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Compound Information
Molecular Weight:178.3138
Molecular Formula:C13H22
InChIKey:DBVAJHPLJNRCCW-TXEJJXNPSA-N
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Compound Information
Molecular Weight:182.2164
Molecular Formula:C10H14O3
InChIKey:HIQFRGLTBWRGKG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.758
Molecular Formula:C12H18CuLi
InChIKey:BATNWSLDCAGAKD-QUIOPKCXSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:TUGFZBPKNAATHG-VQHVLOKHSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:NUVCRNFERWWSQN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2447
Molecular Formula:C11H16
InChIKey:IUJUNEVKAIOLIM-LHBSJXCKSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:YSPWXBGLXDOAKK-HTQZYQBOSA-N
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Compound Information
Molecular Weight:178.274
Molecular Formula:C11H18N2
InChIKey:QMEOYIUHDLFDJB-SFEFJYQLSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:RCOCEQNSBVEVIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:231.935
Molecular Formula:C7H6Cl4
InChIKey:GOEMOMVRHBQQAL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.1225
Molecular Formula:C7H6
InChIKey:AMSMVCOBCOZLEE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:DKJLGFFAXRMQCX-DTORHVGOSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:HLESNNRQHRNVIP-RKDXNWHRSA-N
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Compound Information
Molecular Weight:194.2271
Molecular Formula:C11H14O3
InChIKey:MRJXISKODIYYTK-SFYZADRCSA-N
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Compound Information
Molecular Weight:150.2606
Molecular Formula:C11H18
InChIKey:UZAYYMIBUZEMAI-QSNNZYTBSA-N
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Compound Information
Molecular Weight:246.2652
Molecular Formula:C12H14N4O2
InChIKey:SCZABRZTQLKPSS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:NJUHKLKUSKDEGO-UHFFFAOYSA-N
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Molecular Weight:246.2652
Molecular Formula:C12H14N4O2
InChIKey:MEJGORHHAVJUIL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:CPJYVNNTJIPSHQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.3975
Molecular Formula:C13H22O3Si
InChIKey:TYTOKFJBSJDDHX-WQLSENKSSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:HEVUQAGQTDJLAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:GCNBXIOWQNCARN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:HQGYGGZHZWXFSI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:GGDCGFVZWZWYFA-ZZTMBZGHSA-N
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Compound Information
Molecular Weight:231.935
Molecular Formula:C7H6Cl4
InChIKey:TXGUCUYIZDHFNB-UHFFFAOYSA-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:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:150.2606
Molecular Formula:C11H18
InChIKey:DTIMRZHGSBVJJQ-ZJUUUORDSA-N
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Compound Information
Molecular Weight:128.599
Molecular Formula:C7H9Cl
InChIKey:WIUDTIPPZJTVMD-RQJHMYQMSA-N
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Compound Information
Molecular Weight:122.1677
Molecular Formula:C7H10N2
InChIKey:RXJWCPYHYQNSMU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.4308
Molecular Formula:C16H22OSi
InChIKey:OCBBMQFLQOIGKE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:GGDCGFVZWZWYFA-ZZTMBZGHSA-N
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Compound Information
Molecular Weight:186.2497
Molecular Formula:C13H14O
InChIKey:VGCNDPFMGPLGEY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.4308
Molecular Formula:C16H22OSi
InChIKey:XDUAGDNFMSDTID-LFIBNONCSA-N
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Compound Information
Molecular Weight:85.1475
Molecular Formula:C5H11N
InChIKey:Not Available
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Compound Information
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:JDQMYZVQKVSYEV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:179.2004
Molecular Formula:C6H18N3OP
InChIKey:GNOIPBMMFNIUFM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.205
Molecular Formula:C9H12N2
InChIKey:GSQXJHFCXWQVPL-NPPUSCPJSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:XZINJUKTBVVFBT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:RTZKZFJDLAIYFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:UELXGWDNJAIKGH-KCJUWKMLSA-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:158.1965
Molecular Formula:C11H10O
InChIKey:JNRKVVIKJKHAJM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:SAFIHMIEMQFPDA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:CITYGYUXZWAZMG-IVZJMYDKSA-N
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Compound Information
Molecular Weight:182.2164
Molecular Formula:C10H14O3
InChIKey:KCVWZWPVAVHGJO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:CJTXNSXMYCBHQB-ZHFSPANRSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:CHVJITGCYZJHLR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:MEMQWLUDROWPHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1864
Molecular Formula:C10H10
InChIKey:WYCSHNJRPHQXEY-ZYUZMQFOSA-N
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Compound Information
Molecular Weight:199.077
Molecular Formula:C10H8Cl2
InChIKey:XWSYNELLIUSTQP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:ODQNESGJHJMJOD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.5209
Molecular Formula:C17H32OSi
InChIKey:KVHOBQPKFHEIRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2072
Molecular Formula:C12H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:264.36
Molecular Formula:C16H24O3
InChIKey:RAOUQQAZAMHGSV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1916
Molecular Formula:C9H12
InChIKey:XIYBUZZTBWMHIR-ASODMVGOSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:Not Available
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:CLKFESRGQCZCQW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.395
Molecular Formula:C16H20S
InChIKey:PNIJMJDZDAURBU-HOCLYGCPSA-N
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Compound Information
Molecular Weight:328.4022
Molecular Formula:C20H24O4
InChIKey:ZMASTBKEUGZKDL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.212
Molecular Formula:C4H9KO
InChIKey:LPNYRYFBWFDTMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:ITFCMGFMRLGLSS-SCZZXKLOSA-N
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Compound Information
Molecular Weight:576.338
Molecular Formula:C21H22Cl4O6S2
InChIKey:ICGBSQZJTJDOQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.165
Molecular Formula:C8H10
InChIKey:VTYQQMGYHHVPMX-SFYZADRCSA-N
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Compound Information
Molecular Weight:194.184
Molecular Formula:C10H10O4
InChIKey:NIQCNGHVCWTJSM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2542
Molecular Formula:C12H16O2
InChIKey:QBMVEZRZZZCBKI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.1965
Molecular Formula:C11H10O
InChIKey:ZZRHQPNHZAPVOY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:JCIHTLANYGNMGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:SKKTZNHVYFHGDC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2548
Molecular Formula:C12H16O
InChIKey:PJCXURHEWBLKAF-KOLCDFICSA-N
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Compound Information
Molecular Weight:120.1916
Molecular Formula:C9H12
InChIKey:XOKYBNQQPOTRHZ-UHFFFAOYSA-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:286.3224
Molecular Formula:C17H18O4
InChIKey:MTFILACMLRJCNQ-GYGLHTOKSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:HEVUQAGQTDJLAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:JTUCTIYXBCLENQ-NDDURPPSSA-N
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Compound Information
Molecular Weight:116.1598
Molecular Formula:C9H8
InChIKey:YBYIRNPNPLQARY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.13
Molecular Formula:C5H11NaO
InChIKey:CGRKYEALWSRNJS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.1965
Molecular Formula:C11H10O
InChIKey:WMMQEAXDGPIZJS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.4411
Molecular Formula:C14H26OSi
InChIKey:GXZHKWWFRGMDHV-GXDHUFHOSA-N
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Compound Information
Molecular Weight:474.6295
Molecular Formula:C28H42O6
InChIKey:TYIXBSJXUFTELJ-VQXHGYQESA-N
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Compound Information
Molecular Weight:182.2164
Molecular Formula:C10H14O3
InChIKey:FBWJHXUJWLNFMU-UHFFFAOYSA-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:118.1757
Molecular Formula:C9H10
InChIKey:TYYFDJUFUOSPFB-XGEHTFHBSA-N
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:GIYGGESUOAACLE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.616
Molecular Formula:C10H7Cl
InChIKey:WTDWEQFMBJKEOH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.2497
Molecular Formula:C13H14O
InChIKey:VQNGRZLFVLQCBM-NEPJUHHUSA-N
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Compound Information
Molecular Weight:280.5209
Molecular Formula:C17H32OSi
InChIKey:NMBTYQIXNPPWAH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.3334
Molecular Formula:C15H22O3
InChIKey:UWHSAVGBHRWSLX-VBJDMCQTSA-N
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Compound Information
Molecular Weight:120.1916
Molecular Formula:C9H12
InChIKey:DWMIBKBRGDVWIN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:SFSYEMMJCAYBGK-DAXSKMNVSA-N
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Compound Information
Molecular Weight:250.3334
Molecular Formula:C15H22O3
InChIKey:FKLOWKGYXJDDJJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:334.3481
Molecular Formula:C21H19O2P
InChIKey:Not Available
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Compound Information
Molecular Weight:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-UHFFFAOYSA-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:164.2011
Molecular Formula:C10H12O2
InChIKey:IXNFXAHCEDDXAK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:CBEAQHBVDAQDGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:MEMQWLUDROWPHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:230.2592
Molecular Formula:C14H14O3
InChIKey:WKJDBPKLFIZZGH-CDRMENOJSA-N
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Compound Information
Molecular Weight:145.201
Molecular Formula:C10H11N
InChIKey:SXYMSGVQTKLDFC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:158.1965
Molecular Formula:C11H10O
InChIKey:WKJSBFXJGZJVET-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.765
Molecular Formula:C11H12CuLiS
InChIKey:OEDRLCPGDVZUPY-UHFFFAOYSA-M
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:BSUDRRGVKNXULI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:318.495
Molecular Formula:C24H30
InChIKey:MVZVDAGWAAZJPE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:286.3224
Molecular Formula:C17H18O4
InChIKey:HRJJYHBUEXWMNQ-CABCVRRESA-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:231.13
Molecular Formula:C10H15BrO
InChIKey:FMNGDHYMVNYZJE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:328.4022
Molecular Formula:C20H24O4
InChIKey:XXOIZBAUCQNUGS-YAHCETOVSA-N
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Compound Information
Molecular Weight:353.458
Molecular Formula:C21H27N3O2
InChIKey:GITSGAOIQHAXTO-NRJHNQFBSA-N
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Compound Information
Molecular Weight:224.4146
Molecular Formula:C13H24OSi
InChIKey:HGOIKGVYASTKAI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.395
Molecular Formula:C16H20S
InChIKey:HAYIDNZNMPSQEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.1916
Molecular Formula:C9H12
InChIKey:OLNXIBCIPUFDHP-DTWKUNHWSA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:312.4458
Molecular Formula:C21H28O2
InChIKey:CTNIMHKALLVGSJ-WSGPNKEYSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:CDWAKLKSWYVUSL-GQCTYLIASA-N
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Compound Information
Molecular Weight:84.0734
Molecular Formula:C4H4O2
InChIKey:IMAKHNTVDGLIRY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.1745
Molecular Formula:C9H10O2
InChIKey:FUQXBIVRQRQWJQ-WPZUCAASSA-N
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Compound Information
Molecular Weight:284.3065
Molecular Formula:C17H16O4
InChIKey:IQHVNIOPVRHEBW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1677
Molecular Formula:C7H10N2
InChIKey:RXJWCPYHYQNSMU-KNVOCYPGSA-N
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Compound Information
Molecular Weight:122.1677
Molecular Formula:C7H10N2
InChIKey:RXJWCPYHYQNSMU-BQBZGAKWSA-N
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:UEYYOGFVPAORCH-KNVOCYPGSA-N
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Compound Information
Molecular Weight:98.1789
Molecular Formula:C7H10
InChIKey:Not Available
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Compound Information
Molecular Weight:98.1789
Molecular Formula:C7H10
InChIKey:Not Available
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Compound Information
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:GWYPDXLJACEENP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:PCTQXTPEUWPMPH-CDGHSHMBSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:PCTQXTPEUWPMPH-VKTMEOEOSA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:PCTQXTPEUWPMPH-AEDVTNKESA-N
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Compound Information
Molecular Weight:108.1809
Molecular Formula:C8H12
InChIKey:PCTQXTPEUWPMPH-LFHXBRCSSA-N
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Compound Information
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:TTYIJTXBBRUWBF-CMTQZWALSA-N
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Compound Information
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:TTYIJTXBBRUWBF-RHCSFITRSA-N
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Compound Information
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:TTYIJTXBBRUWBF-NYDMHHSESA-N
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Compound Information
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:TTYIJTXBBRUWBF-VTPQSVFASA-N
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Compound Information
Molecular Weight:122.2075
Molecular Formula:C9H14
InChIKey:DKJLGFFAXRMQCX-IUCAKERBSA-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:150.2606
Molecular Formula:C11H18
InChIKey:UZAYYMIBUZEMAI-ZXXKLBARSA-N
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Compound Information
Molecular Weight:150.2606
Molecular Formula:C11H18
InChIKey:UZAYYMIBUZEMAI-IJUHFESZSA-N
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Compound Information
Molecular Weight:150.2606
Molecular Formula:C11H18
InChIKey:IRKYSUMPMNRVDS-NSHDSACASA-N
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Compound Information
Molecular Weight:150.2606
Molecular Formula:C11H18
InChIKey:IRKYSUMPMNRVDS-LLVKDONJSA-N
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Compound Information
Molecular Weight:150.2606
Molecular Formula:C11H18
InChIKey:UZAYYMIBUZEMAI-UOECRDIDSA-N
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Compound Information
Molecular Weight:148.2447
Molecular Formula:C11H16
InChIKey:KIFXGGYCNMHCSX-BAQGIRSFSA-N
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Compound Information
Molecular Weight:148.2447
Molecular Formula:C11H16
InChIKey:IUJUNEVKAIOLIM-WYJIDPQJSA-N
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Compound Information
Molecular Weight:150.2606
Molecular Formula:C11H18
InChIKey:DTIMRZHGSBVJJQ-NXEZZACHSA-N
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Compound Information
Molecular Weight:178.3138
Molecular Formula:C13H22
InChIKey:DBVAJHPLJNRCCW-VXGBXAGGSA-N
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Compound Information
Molecular Weight:258.4308
Molecular Formula:C16H22OSi
InChIKey:XDUAGDNFMSDTID-QWNIKGHISA-N
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Compound Information
Molecular Weight:244.395
Molecular Formula:C16H20S
InChIKey:PNIJMJDZDAURBU-GOEBONIOSA-N
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Compound Information
Molecular Weight:286.3224
Molecular Formula:C17H18O4
InChIKey:MTFILACMLRJCNQ-MBKWQPFDSA-N
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Compound Information
Molecular Weight:286.3224
Molecular Formula:C17H18O4
InChIKey:HRJJYHBUEXWMNQ-HUUCEWRRSA-N
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Compound Information
Molecular Weight:286.3224
Molecular Formula:C17H18O4
InChIKey:MTFILACMLRJCNQ-MQGMYGBOSA-N
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Compound Information
Molecular Weight:286.3224
Molecular Formula:C17H18O4
InChIKey:MTFILACMLRJCNQ-GKGCGFJXSA-N
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Compound Information
Molecular Weight:286.3224
Molecular Formula:C17H18O4
InChIKey:HRJJYHBUEXWMNQ-LSDHHAIUSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:GCNBXIOWQNCARN-NXEZZACHSA-N
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Compound Information
Molecular Weight:312.4458
Molecular Formula:C21H28O2
InChIKey:XBMICEPMNNMHED-UXHICEINSA-N
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Compound Information
Molecular Weight:107.1712
Molecular Formula:C8H10
InChIKey:Not Available
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Compound Information
Molecular Weight:107.1712
Molecular Formula:C8H10
InChIKey:Not Available
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Compound Information
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:JBVCYDCDMVOVHU-MAUMQABQSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:UCYPWSYSMRULKS-LDYMZIIASA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:UCYPWSYSMRULKS-KCJUWKMLSA-N
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Compound Information
Molecular Weight:262.3441
Molecular Formula:C16H22O3
InChIKey:NDOKIAQSZLOHNB-SLEUVZQESA-N
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Compound Information
Molecular Weight:234.2909
Molecular Formula:C14H18O3
InChIKey:YOCYKDPDPGMXLH-QPJJXVBHSA-N
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Compound Information
Molecular Weight:302.388
Molecular Formula:C17H18O3S
InChIKey:DJSIWDBJWGSERW-MDZDMXLPSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:LIFGIFYPFPUXMX-WJTVCTBASA-N
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Compound Information
Molecular Weight:266.223
Molecular Formula:C11H16LiO3PS
InChIKey:YSLKBGBTDBNFRE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:384.473
Molecular Formula:C25H21PS
InChIKey:FZZJYLXPYSGTAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:148.2447
Molecular Formula:C11H16
InChIKey:Not Available
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Compound Information
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:OIBNOPICMKFGEM-GLXQMMQGSA-N
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Compound Information
Molecular Weight:270.389
Molecular Formula:C17H18OS
InChIKey:UAYLCAGIJWNVAF-AULVFQMTSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:DHTCPOCLWDZNEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.2903
Molecular Formula:C14H18O4
InChIKey:ODFOEFLMHGBUHY-JKIOLJMWSA-N
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Compound Information
Molecular Weight:222.3987
Molecular Formula:C13H22OSi
InChIKey:DBNLESUOWRDVBT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:416.472
Molecular Formula:C25H21O2PS
InChIKey:PIJCACKAVQQTPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3441
Molecular Formula:C16H22O3
InChIKey:PIKQVXROYXMZHF-SPGJAERMSA-N
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Compound Information
Molecular Weight:232.3181
Molecular Formula:C15H20O2
InChIKey:VBARQDIKXWNABC-UEKVPHQBSA-N
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Compound Information
Molecular Weight:426.5452
Molecular Formula:C26H34O5
InChIKey:NBRNOXUZSYDCNF-OXUURNJGSA-N
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Compound Information
Molecular Weight:204.308
Molecular Formula:C14H20O
InChIKey:FOHAYQHTQXKQAC-ALCCZGGFSA-N
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Compound Information
Molecular Weight:275.3013
Molecular Formula:C18H13NO2
InChIKey:AYHSMADDXZUZBX-NJKRNUQASA-N
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Compound Information
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:QPUODTOFTADTPC-NUGNTBJXSA-N
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Compound Information
Molecular Weight:176.2548
Molecular Formula:C12H16O
InChIKey:ZIPLHJSRWHXOQA-DQIWSBTHSA-N
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Compound Information
Molecular Weight:450.909
Molecular Formula:C23H27ClO7
InChIKey:UZGBDXNYPDBPEE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:464.7855
Molecular Formula:C25H44O4Si2
InChIKey:GEIHMYSOESNZMY-QQUHULSZSA-N
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Compound Information
Molecular Weight:266.4082
Molecular Formula:C14H22O3Si
InChIKey:KPGYLZPPHJXZLH-MNOVXSKESA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:UVYBUILFPHGICE-OUAUKWLOSA-N
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Compound Information
Molecular Weight:358.4727
Molecular Formula:C25H26O2
InChIKey:VIOFBJNSTNGVNV-MOUTVQLLSA-N
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Compound Information
Molecular Weight:126.583
Molecular Formula:C7H7Cl
InChIKey:HMCDTIPTNPHHQW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:VYHWQHYSUMPIHU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:498.7263
Molecular Formula:C29H42O5Si
InChIKey:DNOLFSWCWWZZMJ-SCALINHKSA-N
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Compound Information
Molecular Weight:292.5316
Molecular Formula:C18H32OSi
InChIKey:UUOQUUKXKGZSAE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:WKIGPOWBDOSHHL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:HALCXXAVLJHSTJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:XEVMBGZGFURZIR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.2179
Molecular Formula:C13H10O
InChIKey:RWCCWEUUXYIKHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:WIKOFOVLTJGZPZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:356.4569
Molecular Formula:C25H24O2
InChIKey:BIIWFDZRIJZRFJ-UOHRICOVSA-N
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Compound Information
Molecular Weight:164.2011
Molecular Formula:C10H12O2
InChIKey:BGQVJSGWDPCSBT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:250.2903
Molecular Formula:C14H18O4
InChIKey:IAHQWFWTHFDOSW-CNNDECALSA-N
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Compound Information
Molecular Weight:440.5717
Molecular Formula:C27H36O5
InChIKey:DSTHMYSFFOMCLS-JERKJWEBSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:XJNMAPSTMQHAAD-ONGXEEELSA-N
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