Standard Article

The Nazarov Cyclization

  1. Karl L. Habermas1,
  2. Scott E. Denmark1,
  3. Todd K. Jones2

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or045.01

Organic Reactions

Organic Reactions

How to Cite

Habermas, K. L., Denmark, S. E. and Jones, T. K. 2004. The Nazarov Cyclization. Organic Reactions. 45:1:1–158.

Author Information

  1. 1

    University of Illinois, Department of Chemistry, Urbana, Illinois

  2. 2

    Ligand Pharmaceuticals Inc., San Diego, California

Publication History

  1. Published Online: 15 OCT 2004

Chemistry Terms

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Abstract

The Nazarov cyclization is named after the eminent Russian chemist I. N. Nazarov (1900–1957). In the course of an extensive study on the formation of allyl vinyl ketones by the mercuric ion and acid-catalyzed hydration of dienynes, Nazarov and his co-workers discovered a secondary reaction to form 2-cyclopentenones. Nazarov initially formulated a direct acid-catalyzed closure of the allyl vinyl ketones and demonstrated the preparation of 2-cyclopentenones from these precursors in dozens of cases. However in 1952, Braude and Coles suggested the intermediacy of carbocations and demonstrated that the formation of 2-cyclopentenones actually proceeds via the α,α′-divinyl ketones. This fact, together with further mechanistic clarification, has led to the current formulation of the Nazarov cyclization as the acid-catalyzed closure of divinyl ketones to 2-cyclopentenones.

This process was already documented in 1903. Treatment of dibenzylideneacetone with concentrated sulfuric acid and acetic anhydride followed by mild alkaline hydrolysis afforded a ketol, the correct structure of which was finally proposed in 1955. Other examples of acid-catalyzed cyclizations of divinyl ketones exist in the early literature, as do reactions which must have proceeded via divinyl ketones.

A broader definition of the Nazarov cyclization includes a wide variety of precursors that under specific reaction conditions also produce 2-cyclopentenones via divinyl ketones or their functional equivalents. A case in point is the formation of a cyclopentenone by treatment of either divinyl ketone or tetrahydropyrone with ethanolic hydrochloric acid. It is the structural variety of precursors that lends versatility to the Nazarov cyclization and which also serves as the organizational framework for this chapter.

To facilitate presentation, the reaction is divided into six categories defined by the structure of the precursor: (1) cyclization of divinyl and allyl vinyl ketones, (2) cyclization of silylated (stannylated) divinyl ketones, (3) in situ generation/cyclization of divinyl ketones or equivalents, (4) generation/cyclization of divinyl ketone equivalents by solvolysis, (5) alkyne-based precursors of divinyl ketones, and (6) coupling reactions to form and cyclize divinyl ketones. The logic of this sequence follows from the order of decreasing structural similarity of the precursors to divinyl ketones. This is intended to be comprehensive in the coverage of cyclizations which produce 2-cyclopentenones. The related electrocyclic closure of less oxidized pentadienylic cations is not covered. The reaction was most recently reviewed in 1991. Prior to that, the Nazarov cyclization had been reviewed in 1983 and also in the context of pentannulation.

Keywords:

  • Nazarov cyclization;
  • scope;
  • limitations;
  • mechanisms;
  • precursors;
  • divinyl ketones;
  • allyl vinyl ketones;
  • silyated divinyl ketones;
  • in situ generation;
  • acetylene;
  • coupling;
  • beta eliminations;
  • acyclic precursors;
  • cyclic precursors;
  • solvolysis;
  • organometallices;
  • scope;
  • limitation;
  • experimental procedures;
  • in situ construction

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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:OZINNMSRADJFGT-VMPITWQZSA-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:219.2365
Molecular Formula:C12H13NO3
InChIKey:ZNSDCFNBAWNVGU-BDAKNGLRSA-N
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Compound Information
Molecular Weight:204.308
Molecular Formula:C14H20O
InChIKey:FQVCRLDGFUDZLP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.3984
Molecular Formula:C18H26O
InChIKey:YDIORERGQVQVDE-XUJLQICISA-N
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Compound Information
Molecular Weight:341.616
Molecular Formula:C16H11Cl3O2
InChIKey:HVFXXGHPXZOZMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:OSJBNOIWECYILA-QDEBKDIKSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:TYOHIOSBKBCTGV-ZCOYIIAOSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:XIQZWXRTLOQFCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3456
Molecular Formula:C19H18O
InChIKey:FPMNYEMWMGKIKG-UHFFFAOYSA-N
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Molecular Weight:222.2802
Molecular Formula:C13H18O3
InChIKey:HWCMBVSIYRTMCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:VNZLXHULMGQBBV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:VGXASKAGJHQIAQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.2762
Molecular Formula:C14H16O
InChIKey:UKXBXZZLVDWYEN-CMDGGOBGSA-N
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Compound Information
Molecular Weight:264.3615
Molecular Formula:C19H20O
InChIKey:YOPQDPIXXPUUCD-KNCCTNLNSA-N
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Compound Information
Molecular Weight:286.753
Molecular Formula:C17H15ClO2
InChIKey:RIACJBJTVDXAMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:BDINBSUUIUWFNH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:307.171
Molecular Formula:C16H12Cl2O2
InChIKey:RHUCGJFEPAJWNX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.2497
Molecular Formula:C13H14O
InChIKey:MOLIPKPQUNOLPS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.308
Molecular Formula:C14H20O
InChIKey:CXAZLUPBTPWMBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:IUEXCSQSZKSTBV-SOFGYWHQSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:JBKOITKOCSUMJU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:386.067
Molecular Formula:C16H11BrCl2O2
InChIKey:WNMJGSPJQCCLCP-UHFFFAOYSA-N
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Molecular Weight:325.162
Molecular Formula:C16H11Cl2FO2
InChIKey:VVLSSKANSRKXMP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:DLIOIVADLGYAKX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:PTWDCTVTFUJBTP-AMMQDNIMSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:HZKMMDJFMOCBDN-JXMROGBWSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:JTHVVAXWTIDCJL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.308
Molecular Formula:C14H20O
InChIKey:QPLURCPDRWDWGP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.3346
Molecular Formula:C15H22O
InChIKey:OGGLYJQVKQLORS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:OVTCGEGPTDACTQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:RFKUZZDLAINSOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3068
Molecular Formula:C14H20O3
InChIKey:DMKPJKHBQILTEK-VZUCSPMQSA-N
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Compound Information
Molecular Weight:186.2497
Molecular Formula:C13H14O
InChIKey:GFXUKSMUKHKIGP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:OVUKXBLWPZQINY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3068
Molecular Formula:C14H20O3
InChIKey:AUMYQLFSDKDLRA-KGVSQERTSA-N
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Compound Information
Molecular Weight:133.341
Molecular Formula:AlCl3
InChIKey:VSCWAEJMTAWNJL-UHFFFAOYSA-K
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:WUMGJDIHDFUJTH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:CMQIDSFBRZKDCF-AATRIKPKSA-N
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Compound Information
Molecular Weight:295.3325
Molecular Formula:C18H17NO3
InChIKey:CZACSTFTHHDBHS-AEOIHIIDSA-N
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Compound Information
Molecular Weight:200.2762
Molecular Formula:C14H16O
InChIKey:JKQJKZUOFYQZDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:219.2365
Molecular Formula:C12H13NO3
InChIKey:VFQOTOIXMOEBIM-ZQARSLAVSA-N
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Compound Information
Molecular Weight:328.3591
Molecular Formula:C19H20O5
InChIKey:TZJPQVGVRMARPX-RRCSTGOVSA-N
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Compound Information
Molecular Weight:320.4663
Molecular Formula:C20H32O3
InChIKey:YAAAWJHJNSJVLK-CUWKQTPXSA-N
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Compound Information
Molecular Weight:247.2897
Molecular Formula:C14H17NO3
InChIKey:HREZFCDGTKEJKX-XKSSXDPKSA-N
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Compound Information
Molecular Weight:200.2762
Molecular Formula:C14H16O
InChIKey:XLSVZCWMRCGKIF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:AELCEILSBQJDNN-KXFIGUGUSA-N
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Compound Information
Molecular Weight:286.753
Molecular Formula:C17H15ClO2
InChIKey:CDNLAPAQVBJOIL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.2762
Molecular Formula:C14H16O
InChIKey:ABUVFPGLUDMUGS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.4143
Molecular Formula:C18H28O
InChIKey:XWKFGNZANAEDJJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:296.65
Molecular Formula:HgO4S
InChIKey:DOBUSJIVSSJEDA-UHFFFAOYSA-L
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:ONWVDLXZJFDSKI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:247.2897
Molecular Formula:C14H17NO3
InChIKey:DCDJXOCVNZZFCQ-MNOVXSKESA-N
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Compound Information
Molecular Weight:153.823
Molecular Formula:CCl4
InChIKey:VZGDMQKNWNREIO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:307.171
Molecular Formula:C16H12Cl2O2
InChIKey:XCQVCKFRFDYRJG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.3346
Molecular Formula:C15H22O
InChIKey:KVQGWGYXVZANLO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:QQTOKQJUMJORAY-ALCCZGGFSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:JCQDXLAJHNMEJO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:328.3591
Molecular Formula:C19H20O5
InChIKey:ILKGAHQRSGVBBZ-WQVCFCJDSA-N
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Compound Information
Molecular Weight:162.204
Molecular Formula:Cl3Fe
InChIKey:RBTARNINKXHZNM-UHFFFAOYSA-K
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:AWDIPVATDWHUEJ-YDFGWWAZSA-N
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Compound Information
Molecular Weight:204.308
Molecular Formula:C14H20O
InChIKey:OPNNNPWOVXNXFJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:GNGLZOMSRQEYPY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.106
Molecular Formula:CH4O3S
InChIKey:AFVFQIVMOAPDHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2695
Molecular Formula:C12H18O3
InChIKey:FINFEVDZGXPOFJ-BXXMFMFASA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:QQNCJUZOZNCZLI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:HGKVDALQZGEOJH-QHHAFSJGSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:XDJBXCQPXSFIML-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:BBZXSLQHJFZEBE-VMPITWQZSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:FNSWVLHMKKGFQD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:BMSQLWVXCPXIKM-PSRYSYJVSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:LUOJRDJKWPDJPZ-JBLDHEPKSA-N
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Compound Information
Molecular Weight:200.2762
Molecular Formula:C14H16O
InChIKey:JXKBKGJZBXNRKQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2921
Molecular Formula:C14H18O
InChIKey:QSHFHUWRBSREDR-VDUILEQBSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:ZRVRFRQABNZQLZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.3163
Molecular Formula:C15H20O5
InChIKey:PZZYXESBDRVCNH-DTWKUNHWSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:IEQGUHPWAWGIRY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:141.928
Molecular Formula:C4H10BF3O
InChIKey:MZTVMRUDEFSYGQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:JYFIFUJPUQJKGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.2631
Molecular Formula:C13H16O5
InChIKey:MFKLHWNYBKUURK-ZJUUUORDSA-N
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Compound Information
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:AMUQJUSLJOGVMP-XROYCOCOSA-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:222.258
Molecular Formula:C4H9F3O3SSi
InChIKey:FTVLMFQEYACZNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.078
Molecular Formula:H2O4S
InChIKey:QAOWNCQODCNURD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:AMUQJUSLJOGVMP-XROYCOCOSA-N
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Compound Information
Molecular Weight:176.082
Molecular Formula:Cl3Ga
InChIKey:UPWPDUACHOATKO-UHFFFAOYSA-K
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Compound Information
Molecular Weight:186.2497
Molecular Formula:C13H14O
InChIKey:ZTWQQDRCGWZCKQ-UUILKARUSA-N
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Compound Information
Molecular Weight:200.0935
Molecular Formula:C3H9ISi
InChIKey:CSRZQMIRAZTJOY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:IOCQNUCZKMQLHU-RNCFNFMXSA-N
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Compound Information
Molecular Weight:172.202
Molecular Formula:C7H8O3S
InChIKey:JOXIMZWYDAKGHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3068
Molecular Formula:C14H20O3
InChIKey:ORXXLFAEIYKJIT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:257.955
Molecular Formula:H5O10P3
InChIKey:UNXRWKVEANCORM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:YOKZDALFYWMEHH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:ZSTBALGLNMBYPL-FARCUNLSSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:Not Available
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Compound Information
Molecular Weight:210.2695
Molecular Formula:C12H18O3
InChIKey:HBMRVYMCLAMXCV-ZJUUUORDSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:XAIDJKMHAGUWQN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:SWNIDXDREKMWCF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:XMCFIMTZBPWLIC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2921
Molecular Formula:C14H18O
InChIKey:QSHFHUWRBSREDR-VDUILEQBSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:BCQYOFQAZNHYTB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.377
Molecular Formula:C16H26O
InChIKey:QOKIFEBUOKBZRE-PTNGSMBKSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:WJMAAIUGJBUDLY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2055
Molecular Formula:CK2O3
InChIKey:BWHMMNNQKKPAPP-UHFFFAOYSA-L
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Compound Information
Molecular Weight:308.371
Molecular Formula:C20H20O3
InChIKey:IUQZFUVVLJGXME-XMHGGMMESA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:NKDYJPIVZMBXNR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.3163
Molecular Formula:C15H20O5
InChIKey:PZZYXESBDRVCNH-DTWKUNHWSA-N
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Compound Information
Molecular Weight:252.2631
Molecular Formula:C13H16O5
InChIKey:RPLFDITWLLPMSI-ZJUUUORDSA-N
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Compound Information
Molecular Weight:379.472
Molecular Formula:C22H21NO3S
InChIKey:KBODAUNZLQUMAC-MRXNPFEDSA-N
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Compound Information
Molecular Weight:222.3663
Molecular Formula:C15H26O
InChIKey:HFTYKVIABIXSIE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:IGQGGQLLFGYYFL-WLRTZDKTSA-N
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Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:MHJHXQGYYHAJSC-VXNVDRBHSA-N
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Compound Information
Molecular Weight:373.4
Molecular Formula:C19H18O6S
InChIKey:UQROYXPNJSISTI-BHIYHBOVSA-M
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:PWIYCNRRAWIGBD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:258.3984
Molecular Formula:C18H26O
InChIKey:DFSHJBRCNZZAES-DCWRUNIHSA-N
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Compound Information
Molecular Weight:328.3591
Molecular Formula:C19H20O5
InChIKey:OTYBPIKOUDCLHE-IRZHHCKBSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:CERXIJIPDUUHBT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:HKUSGJUIVWSFAW-FOGDFJRCSA-N
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Compound Information
Molecular Weight:208.2536
Molecular Formula:C12H16O3
InChIKey:ILKHUQNAIMTJKW-XCVCLJGOSA-N
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Compound Information
Molecular Weight:386.067
Molecular Formula:C16H11BrCl2O2
InChIKey:ULUULEQOBVSPGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:IXNYYJARHNGRSX-ZJRFNNFUSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:GNGLZOMSRQEYPY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:UCDRMGOESYJHJP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.4143
Molecular Formula:C18H28O
InChIKey:JLDSOJFRVDTPDV-SAPNQHFASA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:MDQBPZFTVXXHSM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:POIARNZEYGURDG-FNORWQNLSA-N
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Compound Information
Molecular Weight:204.308
Molecular Formula:C14H20O
InChIKey:DCYRGPHYBMPSPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:OSFBPUCJKKZBQF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:WHCFYBLKMUUCBG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:QQTOKQJUMJORAY-ALCCZGGFSA-N
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Compound Information
Molecular Weight:248.319
Molecular Formula:C18H16O
InChIKey:WUYVWTRPPWLTQF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:BZUDJXIQAPEUDV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.52
Molecular Formula:Cl4Sn
InChIKey:Not Available
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Compound Information
Molecular Weight:192.2973
Molecular Formula:C13H20O
InChIKey:IXLLBXDECOMIBP-FNORWQNLSA-N
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Compound Information
Molecular Weight:141.9445
Molecular Formula:O5P2
InChIKey:YWEUIGNSBFLMFL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:341.616
Molecular Formula:C16H11Cl3O2
InChIKey:FOTZESWUEPVLDE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:379.472
Molecular Formula:C22H21NO3S
InChIKey:RTPLFRXNBVKANY-BJZITVGISA-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:124.1803
Molecular Formula:C8H12O
InChIKey:QJQNTXCURBPBOK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:JPFCSCMSXWDZPA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3068
Molecular Formula:C14H20O3
InChIKey:UXRYHVNSGPZGDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3456
Molecular Formula:C19H18O
InChIKey:QEJFSWMOGORAHD-WXUKJITCSA-N
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Compound Information
Molecular Weight:248.319
Molecular Formula:C18H16O
InChIKey:KMNIHRZJBBITIA-SAPNQHFASA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:FRJCBSYBOWIKCF-VZGHUFTCSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:VKMPHJINXYTSIM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.377
Molecular Formula:C16H26O
InChIKey:COXWOSURKUIXRK-ZPJJMXRQSA-N
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Compound Information
Molecular Weight:46.0254
Molecular Formula:CH2O2
InChIKey:BDAGIHXWWSANSR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:127.91241
Molecular Formula:HI
InChIKey:XMBWDFGMSWQBCA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:NOFSNYQYGQRNMS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.308
Molecular Formula:C14H20O
InChIKey:DVLOSGFHWPRCRC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:97.9952
Molecular Formula:H3O4P
InChIKey:NBIIXXVUZAFLBC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.3346
Molecular Formula:C15H22O
InChIKey:NAWNMTUEMCFTPY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:216.2756
Molecular Formula:C14H16O2
InChIKey:PDSYCLSNNJAUTL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2435
Molecular Formula:C11H16O2
InChIKey:VVUFQBBSDOPLPY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:YEPVCZSUVSKIRZ-SFYZADRCSA-N
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Compound Information
Molecular Weight:320.4663
Molecular Formula:C20H32O3
InChIKey:PKOGCMIOJQMKJN-VGGQSJIBSA-N
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Compound Information
Molecular Weight:186.2497
Molecular Formula:C13H14O
InChIKey:SVXSGMHECCQOJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:280.3163
Molecular Formula:C15H20O5
InChIKey:DBKXMNLULSAGKE-NEPJUHHUSA-N
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Compound Information
Molecular Weight:208.2536
Molecular Formula:C12H16O3
InChIKey:HPNGQWYFGGRHLH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.377
Molecular Formula:C16H26O
InChIKey:RSJCZMMJWOHZNN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:325.162
Molecular Formula:C16H11Cl2FO2
InChIKey:XBWKCMGIKFXXJY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:180.2435
Molecular Formula:C11H16O2
InChIKey:ZRMASKUGHTZHTD-UHFFFAOYSA-N
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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:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:APJNFHYKAHKUCP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:202.2921
Molecular Formula:C14H18O
InChIKey:VNSPYBLCYVIHLJ-NEPJUHHUSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:JRZTUUICGWFQIU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.2762
Molecular Formula:C14H16O
InChIKey:XICYDSRQFDKLBY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:BHWSUESVZDAOGN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:36.461
Molecular Formula:ClH
InChIKey:VEXZGXHMUGYJMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:209.265
Molecular Formula:Cl3Rh
InChIKey:SONJTKJMTWTJCT-UHFFFAOYSA-K
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:MOKAQSNAVCFXIR-XVYDYJIPSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:HGKVDALQZGEOJH-QHHAFSJGSA-N
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Compound Information
Molecular Weight:295.3325
Molecular Formula:C18H17NO3
InChIKey:COPUUGVVTFQZGW-VIRABCJISA-N
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Compound Information
Molecular Weight:222.3663
Molecular Formula:C15H26O
InChIKey:STEKBQXBCBAXRO-BUHFOSPRSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:NDINEAZIWFKJEN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:PECJLLWRMRWDHH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:NDIQNZBBNBMLMR-SNAWJCMRSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:AWDIPVATDWHUEJ-YDFGWWAZSA-N
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Compound Information
Molecular Weight:204.308
Molecular Formula:C14H20O
InChIKey:HMDDYSUKJVUEAW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:SUZMRTGGJHYIBD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:NCCVWTMZTIJUJB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:234.2925
Molecular Formula:C17H14O
InChIKey:WMKGGPCROCCUDY-PHEQNACWSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:HCCAEHCZDSIPAD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:308.371
Molecular Formula:C20H20O3
InChIKey:NBICVCLIDSHKKJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:NCXAJTNGEGRDBR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.3346
Molecular Formula:C15H22O
InChIKey:QEDWNIUIKXMGOE-JURCDPSOSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:IHTGGNOYGQEFON-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:NZPJGHVPFXLJOY-CQCRHSALSA-N
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Compound Information
Molecular Weight:30.973762
Molecular Formula:P
InChIKey:XYFCBTPGUUZFHI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:VGMZRZKQYULQKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:111.1599
Molecular Formula:C7H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:101.0137
Molecular Formula:H3O4P
InChIKey:Not Available
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Compound Information
Molecular Weight:167.2662
Molecular Formula:C11H18O
InChIKey:Not Available
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Compound Information
Molecular Weight:20.0276
Molecular Formula:H2O
InChIKey:Not Available
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:XLOSJJHYKQYOFF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:UAOAMBDPJPMYDO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.2631
Molecular Formula:C13H16O5
InChIKey:MFKLHWNYBKUURK-NXEZZACHSA-N
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Compound Information
Molecular Weight:252.2631
Molecular Formula:C13H16O5
InChIKey:RPLFDITWLLPMSI-NXEZZACHSA-N
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Compound Information
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:LUOJRDJKWPDJPZ-NHCYSSNCSA-N
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Compound Information
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:AMUQJUSLJOGVMP-ONOSFVFSSA-N
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Compound Information
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:IXNYYJARHNGRSX-XKFHPXPTSA-N
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Compound Information
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:AMUQJUSLJOGVMP-WHGOUJPWSA-N
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Compound Information
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:AMUQJUSLJOGVMP-AVPPRXQKSA-N
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Compound Information
Molecular Weight:266.2897
Molecular Formula:C14H18O5
InChIKey:AMUQJUSLJOGVMP-WHGOUJPWSA-N
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Compound Information
Molecular Weight:247.2897
Molecular Formula:C14H17NO3
InChIKey:HREZFCDGTKEJKX-QXFUBDJGSA-N
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Compound Information
Molecular Weight:204.308
Molecular Formula:C14H20O
InChIKey:ZNKNTLTVJTUAFZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.3346
Molecular Formula:C15H22O
InChIKey:QEDWNIUIKXMGOE-NEBZKDRISA-N
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Compound Information
Molecular Weight:295.3325
Molecular Formula:C18H17NO3
InChIKey:COPUUGVVTFQZGW-GBOPCIDUSA-N
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Compound Information
Molecular Weight:328.3591
Molecular Formula:C19H20O5
InChIKey:ILKGAHQRSGVBBZ-MAZHCROVSA-N
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Compound Information
Molecular Weight:328.3591
Molecular Formula:C19H20O5
InChIKey:OTYBPIKOUDCLHE-ZVYLKZBJSA-N
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Compound Information
Molecular Weight:328.3591
Molecular Formula:C19H20O5
InChIKey:ILKGAHQRSGVBBZ-XHAYOOOLSA-N
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Compound Information
Molecular Weight:379.472
Molecular Formula:C22H21NO3S
InChIKey:RTPLFRXNBVKANY-DKSSEZFCSA-N
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Compound Information
Molecular Weight:130.2173
Molecular Formula:C8H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:130.2173
Molecular Formula:C8H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:130.2173
Molecular Formula:C8H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:127.1988
Molecular Formula:C8H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:128.2049
Molecular Formula:C8H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:128.2049
Molecular Formula:C8H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:222.3987
Molecular Formula:C13H22OSi
InChIKey:OPRREFJZZNQBEA-MDZDMXLPSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:CWJMUDRNLYBGAV-SFECMWDFSA-N
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Compound Information
Molecular Weight:176.2548
Molecular Formula:C12H16O
InChIKey:RZVYRHIZBCICFI-KRXBUXKQSA-N
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Compound Information
Molecular Weight:332.5109
Molecular Formula:C22H24OSi
InChIKey:OATVPLIBMPAILN-FOCLMDBBSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:WHXGMHQDSQWUMC-CMDGGOBGSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:DWFQNDXJJAEPMV-XVNBXDOJSA-N
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Compound Information
Molecular Weight:276.4891
Molecular Formula:C17H28OSi
InChIKey:BHZSOSLUEVXKAO-XUMBHXRASA-N
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Compound Information
Molecular Weight:182.2164
Molecular Formula:C10H14O3
InChIKey:GZLOYGNKOOQICR-UWVGGRQHSA-N
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Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:RMBZCEQCJKMJLB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:XAIDJKMHAGUWQN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2548
Molecular Formula:C12H16O
InChIKey:GGIGXMHCJLHREX-NGJJGHSNSA-N
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Compound Information
Molecular Weight:184.2322
Molecular Formula:C10H16O3
InChIKey:KVUYTWLGGPCJNI-NXEZZACHSA-N
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Compound Information
Molecular Weight:222.3987
Molecular Formula:C13H22OSi
InChIKey:DTKOTMYJZJRMHK-VQHVLOKHSA-N
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Compound Information
Molecular Weight:182.3348
Molecular Formula:C10H18OSi
InChIKey:YARWDVPRWIILSG-KHHFIZIMSA-N
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:KNBPFMYLUOGAGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.3227
Molecular Formula:C14H22O3
InChIKey:OYODBKSXIJWQNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:TZJMINBYXYFIGT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.4253
Molecular Formula:C14H24OSi
InChIKey:YJASOCBASBCJMZ-DHZHZOJOSA-N
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Compound Information
Molecular Weight:178.2707
Molecular Formula:C12H18O
InChIKey:VROVLGDPAJTDOE-WCQGTBRESA-N
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Compound Information
Molecular Weight:240.3401
Molecular Formula:C17H20O
InChIKey:XHHIJPWMTITBLY-NUPWCOBBSA-N
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Compound Information
Molecular Weight:194.2701
Molecular Formula:C12H18O2
InChIKey:PBQXIJJNRJGAFX-MKKAVFGOSA-N
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Compound Information
Molecular Weight:453.29
Molecular Formula:C23H42OSn
InChIKey:WUPHSQKDMXCDIU-MWJBMVRFSA-N
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Compound Information
Molecular Weight:222.3987
Molecular Formula:C13H22OSi
InChIKey:UXTDBPZPTLNYNL-CMDGGOBGSA-N
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Compound Information
Molecular Weight:306.5582
Molecular Formula:C19H34OSi
InChIKey:KNXANJHEOXWUTH-OUKQBFOZSA-N
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Compound Information
Molecular Weight:503.35
Molecular Formula:C27H44OSn
InChIKey:XJSWYOHIFJXLAL-GOIPUJLYSA-N
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Compound Information
Molecular Weight:236.4253
Molecular Formula:C14H24OSi
InChIKey:AYXWEPWDBVGDMF-CSKARUKUSA-N
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Compound Information
Molecular Weight:262.4625
Molecular Formula:C16H26OSi
InChIKey:ZZHZZNXUGKAYJB-HNNXBMFYSA-N
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