Standard Article

Catalytic, Asymmetric, Intramolecular Carbon–Hydrogen Insertion

  1. Michael P. Doyle,
  2. Yu Liu,
  3. Maxim Ratnikov

Published Online: 19 APR 2013

DOI: 10.1002/0471264180.or080.01

Organic Reactions

Organic Reactions

How to Cite

P. Doyle, M., Liu, Y. and Ratnikov, M. 2013. Catalytic, Asymmetric, Intramolecular Carbon–Hydrogen Insertion. Organic Reactions. 80:1:1–132.

Author Information

  1. University of Maryland, Department of Chemistry and Biochemistry, College Park, Maryland

Publication History

  1. Published Online: 19 APR 2013

Chemistry Terms

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Abstract

The insertion of a chiral-ligated metal carbene into an aliphatic C-H bond to construct a carbon-carbon bond imparts asymmetry into the resultant molecule to form enantiomerically enriched lactones, lactams, and cycloalkane derivatives and returns the chiral-ligated metal to its catalytically active state. Insertion is favored by electron-donating groups adjacent to the C-H bond that undergoes insertion, and is disfavored by electron-withdrawing groups. Chiral dirhodium(II) carboxamidates have proven to have the greatest breadth of high selectivities, but other classes of catalysts are selective in specific cases. Although there are examples of iodonium ylides as reactants, diazo compounds are the reactants of choice for these reactions. Diazocarbonyl compounds, especially diazoacetates and diazoacetamides, have reactivities and selectivities that are most suitable for high product yields and high stereoselectivities. This reaction is optimally designed for the formation of five-membered ring compounds using diazoacetates and diazoacetamides and of four-membered ring products with constrained diazoacetamides. Access to lignan lactones, baclofen, deoxyxylolactone, and rolipram, among others, exemplify the efficiencies of this methodology relative to other synthetic approaches.

Keywords:

  • insertion;
  • lactones;
  • lactams;
  • cycloalkanes;
  • diazoesters;
  • diazoketones;
  • catalysts;
  • rhodium;
  • copper;
  • metal carbene;
  • enantioselective;
  • experimental conditions

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  1. 1 - 250
Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:528.1227
Molecular Formula:C12H22N2O8Rh2
InChIKey:QGNCFSJCIWCVEJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.62
Molecular Formula:C9H9ClO
InChIKey:MFEILWXBDBCWKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:188.2209
Molecular Formula:C9H16O4
InChIKey:NVFCTEWHWHXMCX-HTQZYQBOSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:DISZALCMKPICJS-WDSKDSINSA-N
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Compound Information
Molecular Weight:198.2621
Molecular Formula:C10H18N2O2
InChIKey:NQJHQUYXNPMZCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.1818
Molecular Formula:C7H12N2O3
InChIKey:POJCVZMVRUJYES-UHFFFAOYSA-N
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Compound Information
Molecular Weight:391.6519
Molecular Formula:C20H33NO3Si2
InChIKey:RKBTUTZGWRHDAG-IAGOWNOFSA-N
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Compound Information
Molecular Weight:166.26
Molecular Formula:C11H18O
InChIKey:ZKWXHMQLBLFZHP-JTQLQIEISA-N
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Compound Information
Molecular Weight:439.4425
Molecular Formula:C20H30N3O6P
InChIKey:UTVGIBNMZSVLTR-MRXNPFEDSA-N
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Compound Information
Molecular Weight:241.2869
Molecular Formula:C11H19N3O3
InChIKey:JFMIMGTXEDLDCY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.3254
Molecular Formula:C13H22N2O3
InChIKey:FBESEAQFADXELM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.2215
Molecular Formula:C9H15NO
InChIKey:BTJJNDMVQJCXFV-MRVPVSSYSA-N
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Compound Information
Molecular Weight:220.2246
Molecular Formula:C11H12N2O3
InChIKey:KURYWUIYBINDOS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:265.305
Molecular Formula:C14H19NO4
InChIKey:AMLLEEPFAAFXKQ-GHMZBOCLSA-N
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Compound Information
Molecular Weight:232.275
Molecular Formula:C14H16O3
InChIKey:SRYYASBMTKGXHC-PYMCNQPYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:AQKZNTBBGPQPBG-BQBZGAKWSA-N
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Compound Information
Molecular Weight:193.2456
Molecular Formula:C10H15N3O
InChIKey:NMGMIIJCSNUJLK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Molecular Weight:220.2246
Molecular Formula:C11H12N2O3
InChIKey:XZQILPCITMHQPT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:312.3597
Molecular Formula:C19H20O4
InChIKey:ZVNMIMFCDTZKSU-QZTJIDSGSA-N
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Compound Information
Molecular Weight:216.2359
Molecular Formula:C12H12N2O2
InChIKey:FAFMZFNIXLNWQU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.2215
Molecular Formula:C9H15NO
InChIKey:LBVHEFWXMHNYHX-HTQZYQBOSA-N
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Compound Information
Molecular Weight:405.6387
Molecular Formula:C19H31N3O3Si2
InChIKey:LANGTPZZMHMAQS-SAABIXHNSA-N
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Compound Information
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:RQLWLQRWDIYLKB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:181.2349
Molecular Formula:C9H15N3O
InChIKey:SSXPKMZQLMMQPK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:442.6737
Molecular Formula:C29H46O3
InChIKey:VRBPQRPEKQITJA-FOFHWNONSA-N
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Compound Information
Molecular Weight:268.3071
Molecular Formula:C17H16O3
InChIKey:NRCUZNVMIOONFH-HOTGVXAUSA-N
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Compound Information
Molecular Weight:514.8011
Molecular Formula:C28H42O5Si2
InChIKey:SQVLRMNPGRRCNA-DQEYMECFSA-N
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Compound Information
Molecular Weight:362.4955
Molecular Formula:C18H26N2O4Si
InChIKey:RJNGZSHWRJLTON-CSKARUKUSA-N
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Compound Information
Molecular Weight:245.234
Molecular Formula:C12H11N3O3
InChIKey:NZGAPIJGMZFXKB-LDYMZIIASA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:DTOLKOPFSXVMBX-APPZFPTMSA-N
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Compound Information
Molecular Weight:285.2964
Molecular Formula:C12H19N3O5
InChIKey:LNICTHUTIYPOAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:350.5386
Molecular Formula:C21H38N2O2
InChIKey:NWUHNCATNYFYMY-KTKRTIGZSA-N
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Compound Information
Molecular Weight:309.3591
Molecular Formula:C19H19NO3
InChIKey:GCVZNCBWWZNCLB-LNLFQRSKSA-N
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Compound Information
Molecular Weight:180.2468
Molecular Formula:C10H16N2O
InChIKey:QGEKXCQULWLGDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:265.3083
Molecular Formula:C13H19N3O3
InChIKey:FTXBYZVQAKUDJU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.2462
Molecular Formula:C10H16N2O2
InChIKey:BIHYWWVPGJQTNO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:SFHMMIVSBBSOJZ-LLVKDONJSA-N
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Compound Information
Molecular Weight:212.2887
Molecular Formula:C11H20N2O2
InChIKey:OVUQWRRSYKDYOL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:267.3208
Molecular Formula:C14H21NO4
InChIKey:LOYTWCAWEKCIDN-DCAQKATOSA-N
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Compound Information
Molecular Weight:166.2203
Molecular Formula:C9H14N2O
InChIKey:KVUOWBVVWWAMCP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:144.1286
Molecular Formula:C5H8N2O3
InChIKey:NUPMZZPPCNECQD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:219.2365
Molecular Formula:C12H13NO3
InChIKey:GCCVRCZMVYRDCO-LDYMZIIASA-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:320.3006
Molecular Formula:C14H16N4O5
InChIKey:HODFFMSWIJTFPK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:309.3591
Molecular Formula:C19H19NO3
InChIKey:FNLYHRIFXCVMMK-RVDLWCBHSA-N
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Compound Information
Molecular Weight:255.3134
Molecular Formula:C12H21N3O3
InChIKey:CDYLNHIIUHMPFX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:UIYNLWMFVBFECH-JGVFFNPUSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:87.1204
Molecular Formula:C4H9NO
InChIKey:YNAVUWVOSKDBBP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:262.3043
Molecular Formula:C14H18N2O3
InChIKey:SLGJXVMEGBBVRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.218
Molecular Formula:C8H19Al
InChIKey:AZWXAPCAJCYGIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:122.1677
Molecular Formula:C7H10N2
InChIKey:VHYFNPMBLIVWCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.63
Molecular Formula:C10H9ClO2
InChIKey:FJIIHITUMSUKIQ-QMMMGPOBSA-N
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Compound Information
Molecular Weight:153.2215
Molecular Formula:C9H15NO
InChIKey:AEAWNPSXVXTRAN-QMMMGPOBSA-N
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Compound Information
Molecular Weight:206.2378
Molecular Formula:C12H14O3
InChIKey:LFLYTOODDXDHGD-SNVBAGLBSA-N
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Compound Information
Molecular Weight:349.3783
Molecular Formula:C18H23NO6
InChIKey:JFLGQUXGKFKXOF-ZYOSVBKOSA-N
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Compound Information
Molecular Weight:411.4291
Molecular Formula:C20H30NO6P
InChIKey:NUKBYOWIEYDSRF-LSJNQWAISA-N
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Compound Information
Molecular Weight:212.2456
Molecular Formula:C10H16N2O3
InChIKey:HUQQGXRPVVKHLI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.2884
Molecular Formula:C14H16N2O3
InChIKey:MHEVIALOYIAMEX-SNVBAGLBSA-N
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Compound Information
Molecular Weight:421.6779
Molecular Formula:C21H35NO4Si2
InChIKey:PEBNASYLAPSXHL-QZTJIDSGSA-N
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Compound Information
Molecular Weight:385.455
Molecular Formula:C25H23NO3
InChIKey:BSZMHCLBPVXXJH-FPKOHDFBSA-N
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Compound Information
Molecular Weight:185.2634
Molecular Formula:C10H19NO2
InChIKey:VOYBHBGQHCAZNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:312.3199
Molecular Formula:C17H16N2O4
InChIKey:HXPZRFPRPAMJSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:121.118
Molecular Formula:CH3N3O2S
InChIKey:BHQIGUWUNPQBJY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:JFVMNDINHUZJDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:261.762
Molecular Formula:C10H14CuO4
InChIKey:QYJPSWYYEKYVEJ-FDGPNNRMSA-L
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Compound Information
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:NOOLISFMXDJSKH-AEJSXWLSSA-N
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Compound Information
Molecular Weight:197.231
Molecular Formula:C10H15NO3
InChIKey:SYVSORJUYOYLOD-HTQZYQBOSA-N
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Compound Information
Molecular Weight:213.2304
Molecular Formula:C10H15NO4
InChIKey:XDPNWLHGKZNDCC-RNFRBKRXSA-N
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Compound Information
Molecular Weight:182.2197
Molecular Formula:C9H14N2O2
InChIKey:ULIFBVLZVLMOST-SFYZADRCSA-N
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Compound Information
Molecular Weight:421.5319
Molecular Formula:C25H31N3O3
InChIKey:SLKIVAROVXOWCI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.3361
Molecular Formula:C14H22N2O3
InChIKey:YKKRUSSGONCGHJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.4247
Molecular Formula:C14H24O2Si
InChIKey:PYJHGLZUNQCGJE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.1678
Molecular Formula:C7H12O4
InChIKey:GSCVZZMSBLVOTD-WDSKDSINSA-N
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Compound Information
Molecular Weight:337.4155
Molecular Formula:C20H23N3O2
InChIKey:RDVMGSCNNQKSLD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:210.2695
Molecular Formula:C12H18O3
InChIKey:DRXIHIVLXWHSPX-YYXYEGJISA-N
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Compound Information
Molecular Weight:121.1796
Molecular Formula:C8H11N
InChIKey:Not Available
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Compound Information
Molecular Weight:142.1525
Molecular Formula:C7H10O3
InChIKey:IJZHVCONXALYLE-PHDIDXHHSA-N
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Compound Information
Molecular Weight:309.3591
Molecular Formula:C19H19NO3
InChIKey:CUDZQQBGALHRAA-RVDLWCBHSA-N
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Compound Information
Molecular Weight:367.3798
Molecular Formula:C17H26N3O4P
InChIKey:UIKIDOXBMPCQKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:JDJMECLBAVIBPW-SNVBAGLBSA-N
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Compound Information
Molecular Weight:433.6919
Molecular Formula:C21H35N3O3Si2
InChIKey:ALGGVMUVZIAOIU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.3282
Molecular Formula:C16H20O3
InChIKey:SPKZCRHTLSLKKU-GJZGRUSLSA-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:227.3
Molecular Formula:C12H21NO3
InChIKey:PUWOOYPDUDSOBG-DTWKUNHWSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:LIMALTCPXVLAQH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:196.0479
Molecular Formula:C4H2F6O2
InChIKey:ZKUJOCJJXCPCFS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:413.341
Molecular Formula:C18H15N5O7
InChIKey:RPEAOLPEJQZRNJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:BXVGGHJBRCDSGU-JTQLQIEISA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:257.283
Molecular Formula:C12H19NO5
InChIKey:NDUOPWMCPCRREV-IONNQARKSA-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:218.2518
Molecular Formula:C12H14N2O2
InChIKey:DUNXLWWHDVEPEF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:65.0099
Molecular Formula:N3Na
InChIKey:PXIPVTKHYLBLMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.2607
Molecular Formula:C13H14N2O5
InChIKey:ZFQBEAWJXQPKKT-KCJUWKMLSA-N
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Compound Information
Molecular Weight:206.3272
Molecular Formula:C13H22N2
InChIKey:QOSSAOTZNIDXMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:309.4021
Molecular Formula:C20H23NO2
InChIKey:CHQPLLRRHZAEDP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:413.4684
Molecular Formula:C25H23N3O3
InChIKey:PAQJORWIVOFVOR-RZFKFIIISA-N
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Compound Information
Molecular Weight:377.6253
Molecular Formula:C19H31NO3Si2
InChIKey:UZDKLFBMKDWAKN-HZPDHXFCSA-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:358.3851
Molecular Formula:C20H22O6
InChIKey:JQLSEYJXODFAEJ-NFBGWVBBSA-N
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Compound Information
Molecular Weight:188.2258
Molecular Formula:C11H12N2O
InChIKey:PFUPLIYCPICYBP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:542.8145
Molecular Formula:C28H42N2O5Si2
InChIKey:PVMWHGWFGBKMTA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.275
Molecular Formula:C14H16O3
InChIKey:FQPOIVSQEMZIEI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.1824
Molecular Formula:C7H12N2O2
InChIKey:ISEKJRTVDNQEHD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:274.315
Molecular Formula:C15H18N2O3
InChIKey:WUNAQTQAHCIRBU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.1992
Molecular Formula:C10H10N2O
InChIKey:ODTNRWGIIUZDHW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:309.4021
Molecular Formula:C20H23NO2
InChIKey:OWCDASIURNGZKP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.275
Molecular Formula:C14H16O3
InChIKey:VHMQJIAYXOPACO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.551
Molecular Formula:CH3ClO2S
InChIKey:QARBMVPHQWIHKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:436.2834
Molecular Formula:C20H21IO3
InChIKey:ROFDSYSZKBBDST-OAHLLOKOSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:ZBRBEWHKLHIEOT-IUCAKERBSA-N
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Compound Information
Molecular Weight:256.3736
Molecular Formula:C11H20N2O3Si
InChIKey:XLIWNMXKBCISIR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:231.2903
Molecular Formula:C14H17NO2
InChIKey:ZIMBAFVDTGHWLE-STQMWFEESA-N
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Compound Information
Molecular Weight:260.2884
Molecular Formula:C14H16N2O3
InChIKey:HRHJATSJLVOSST-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:XSQDTSWAPFCEDH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.0078
Molecular Formula:C6H5IO
InChIKey:Not Available
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Compound Information
Molecular Weight:167.2083
Molecular Formula:C8H13N3O
InChIKey:GEWUCPCTYOJPRM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:82.0338
Molecular Formula:C2H3NaO2
InChIKey:VMHLLURERBWHNL-UHFFFAOYSA-M
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Compound Information
Molecular Weight:330.375
Molecular Formula:C19H22O5
InChIKey:RCQPYMXHGRTMOZ-NHZBNJEXSA-N
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Compound Information
Molecular Weight:253.2943
Molecular Formula:C13H19NO4
InChIKey:GNEJUOUBRPMWSC-NXEZZACHSA-N
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Compound Information
Molecular Weight:23.948
Molecular Formula:HLiO
InChIKey:WMFOQBRAJBCJND-UHFFFAOYSA-M
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:SJBLVTZMVAKOLA-SNVBAGLBSA-N
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Compound Information
Molecular Weight:139.1949
Molecular Formula:C8H13NO
InChIKey:XINDRCTVIBWZGV-ZETCQYMHSA-N
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Compound Information
Molecular Weight:234.2512
Molecular Formula:C12H14N2O3
InChIKey:HVWNLRFMBDWJDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:188.2225
Molecular Formula:C12H12O2
InChIKey:FPFVYUWRIIVBLE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:IFYYFLINQYPWGJ-SECBINFHSA-N
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Compound Information
Molecular Weight:296.3205
Molecular Formula:C17H16N2O3
InChIKey:XAJZCHSDSUSDTG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:467.312
Molecular Formula:C23H19BrN2O4
InChIKey:KAMNKYXWZYDTKW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:MFBXYJLOYZMFIN-JTQLQIEISA-N
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Compound Information
Molecular Weight:213.2768
Molecular Formula:C10H19N3O2
InChIKey:BDTJFNRWTURVHY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:322.5252
Molecular Formula:C21H38O2
InChIKey:FXIPEPUSNDEFHT-VFCOFNOGSA-N
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Compound Information
Molecular Weight:225.2444
Molecular Formula:C10H15N3O3
InChIKey:SAXNTMURWPUYMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:YMRRWQZJYFEWQT-XPUUQOCRSA-N
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Compound Information
Molecular Weight:183.2905
Molecular Formula:C11H21NO
InChIKey:QMCGABRGOSWVFQ-SECBINFHSA-N
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Compound Information
Molecular Weight:320.5093
Molecular Formula:C21H36O2
InChIKey:WJRZRPAZTHFRKY-DSADLTMXSA-N
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Compound Information
Molecular Weight:213.2735
Molecular Formula:C11H19NO3
InChIKey:GLFWQDFZWDKWHW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:340.3731
Molecular Formula:C19H20N2O4
InChIKey:BBAAYUAJKYDSTC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:42.04
Molecular Formula:CH2N2
InChIKey:YXHKONLOYHBTNS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:237.2949
Molecular Formula:C13H19NO3
InChIKey:DMZAEZWAEFVXHS-GHMZBOCLSA-N
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Compound Information
Molecular Weight:213.2735
Molecular Formula:C11H19NO3
InChIKey:UWIOULGMXTZEAH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.2905
Molecular Formula:C11H21NO
InChIKey:FSIDMWFDIXGTCY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.2252
Molecular Formula:C11H12N2O2
InChIKey:UEQCSMLHVJCXDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.2884
Molecular Formula:C14H16N2O3
InChIKey:AKWYJLJFNMRFIK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:419.6653
Molecular Formula:C20H33N3O3Si2
InChIKey:YTKWRQPHAAFIOB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.1931
Molecular Formula:C8H12N2O2
InChIKey:ZBHVRTGDBRNTAE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.198
Molecular Formula:C10H10N2O3
InChIKey:NKBHCKNQZTWVBQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:349.4214
Molecular Formula:C19H27NO5
InChIKey:WOBYBSVGWJQUOF-WBTZKQGOSA-N
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Compound Information
Molecular Weight:212.615
Molecular Formula:CCuF3O3S
InChIKey:YNYHGRUPNQLZHB-UHFFFAOYSA-M
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Compound Information
Molecular Weight:259.3037
Molecular Formula:C14H17N3O2
InChIKey:FNOGAVPQVJOTSI-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:442.6737
Molecular Formula:C29H46O3
InChIKey:GJHCDIVMINMZHK-USZMGKNZSA-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:218.2518
Molecular Formula:C12H14N2O2
InChIKey:YOIBIYKYSCWYJI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:166.2203
Molecular Formula:C9H14N2O
InChIKey:WKSHCSHMPFUNJH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:112.557
Molecular Formula:C6H5Cl
InChIKey:MVPPADPHJFYWMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:241.2438
Molecular Formula:C10H15N3O4
InChIKey:MSURGXZDZWCWPY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.1152
Molecular Formula:C5H8O3
InChIKey:FREVCKUTSMQJOO-BYPYZUCNSA-N
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Compound Information
Molecular Weight:170.1659
Molecular Formula:C7H10N2O3
InChIKey:NGIMHMIVDUEXEX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:201.06
Molecular Formula:C8H9BrO
InChIKey:ZKSOJQDNSNJIQW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:398.3694
Molecular Formula:C19H18N4O6
InChIKey:ATOAHAGIJOKSEM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:HEWVYVNDGPNJQQ-YFKPBYRVSA-N
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Compound Information
Molecular Weight:153.2215
Molecular Formula:C9H15NO
InChIKey:HGDAMVWHTNMRLW-APPZFPTMSA-N
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Compound Information
Molecular Weight:194.184
Molecular Formula:C10H10O4
InChIKey:KSEBMYQBYZTDHS-HWKANZROSA-N
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Compound Information
Molecular Weight:234.2512
Molecular Formula:C12H14N2O3
InChIKey:BARCUOQTGWQYQA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:PQANGXXSEABURG-LURJTMIESA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:339.3664
Molecular Formula:C17H26NO4P
InChIKey:GEISONGUTVPIFW-LSDHHAIUSA-N
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Compound Information
Molecular Weight:385.455
Molecular Formula:C25H23NO3
InChIKey:RZYJEMFEDSQADE-HWBMXIPRSA-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:492.163
Molecular Formula:C3H3F9O9S3Sc
InChIKey:HZXJVDYQRYYYOR-UHFFFAOYSA-K
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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:292.392
Molecular Formula:C13H24O5S
InChIKey:JIVQGIPNGILBKJ-GFCCVEGCSA-N
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Compound Information
Molecular Weight:405.6785
Molecular Formula:C21H35NO3Si2
InChIKey:YLJFWWMVOFJMPY-QZTJIDSGSA-N
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Compound Information
Molecular Weight:152.1473
Molecular Formula:C8H8O3
InChIKey:MWOOGOJBHIARFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:169.264
Molecular Formula:C10H19NO
InChIKey:OFLCVEGJJUMPQB-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:393.3878
Molecular Formula:C19H23NO8
InChIKey:HVISAZUBCZSCHJ-PYNWJHIZSA-N
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Compound Information
Molecular Weight:198.2621
Molecular Formula:C10H18N2O2
InChIKey:FKCWAUQIIPLMRM-SECBINFHSA-N
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Compound Information
Molecular Weight:222.671
Molecular Formula:C11H11ClN2O
InChIKey:TXJXTMZENSBBRT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:315.2446
Molecular Formula:C14H12F3NO4
InChIKey:YYCZPCIFFIRGRZ-LFKKORROSA-N
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Compound Information
Molecular Weight:224.2994
Molecular Formula:C12H20N2O2
InChIKey:ARIRLMOIPLAKEK-VWYCJHECSA-N
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Compound Information
Molecular Weight:224.2563
Molecular Formula:C11H16N2O3
InChIKey:KHKGYIHQRSTCKT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:292.2872
Molecular Formula:C14H16N2O5
InChIKey:CGNHFFXTRKXPJO-SKDRFNHKSA-N
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Compound Information
Molecular Weight:128.0862
Molecular Formula:C4H4N2O3
InChIKey:AWXVZQXIMPKRGJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.3016
Molecular Formula:C15H18O3
InChIKey:PADHXKBQVDPIKC-WUJWULDRSA-N
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Compound Information
Molecular Weight:441.9871
Molecular Formula:C8H12O8Rh2
InChIKey:SYBXSZMNKDOUCA-UHFFFAOYSA-J
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Compound Information
Molecular Weight:183.1216
Molecular Formula:C6H5N3O4
InChIKey:QTZFYMCHQMNSNL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:156.609
Molecular Formula:C8H9ClO
InChIKey:HZFRKZWBVUJYDA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:470.6871
Molecular Formula:C29H46N2O3
InChIKey:NXCBQAWNTDWDHT-ZPXMYGNSSA-N
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Compound Information
Molecular Weight:442.6737
Molecular Formula:C29H46O3
InChIKey:WDIPJZDMYBRZLL-YDLIUSEBSA-N
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Compound Information
Molecular Weight:825.1895
Molecular Formula:C51H60O6Si2
InChIKey:LCMANBPQLCBGAC-PWLYXOBOSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:YGHCAHWARGVWQD-CBAPKCEASA-N
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Compound Information
Molecular Weight:144.1684
Molecular Formula:C7H12O3
InChIKey:XDFNRFOJIYGFRY-ZETCQYMHSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:168.1931
Molecular Formula:C8H12N2O2
InChIKey:ZRDDLFZEMCNMBB-ONEGZZNKSA-N
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Compound Information
Molecular Weight:234.2909
Molecular Formula:C14H18O3
InChIKey:JCVSIOSZMZEYJB-ALCCZGGFSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:WXEMDVAITHCACX-KYHHOPLUSA-N
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Compound Information
Molecular Weight:256.2964
Molecular Formula:C16H16O3
InChIKey:CPIKEDMPXDEUED-UHFFFAOYSA-N
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Compound Information
Molecular Weight:200.1919
Molecular Formula:C8H12N2O4
InChIKey:CVTQSOLUWLVTHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:393.5185
Molecular Formula:C25H31NO3
InChIKey:SXZBIMLSZLVAIN-IBGZPJMESA-N
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Compound Information
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:UDBSCEBMGHOBRS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1023
Molecular Formula:C6H5F
InChIKey:Not Available
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Compound Information
Molecular Weight:261.3163
Molecular Formula:C15H19NO3
InChIKey:OVWKIBNNCGGPPH-NEPJUHHUSA-N
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Compound Information
Molecular Weight:269.297
Molecular Formula:C12H19N3O4
InChIKey:WDFCDIPQLBAYRS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:FWFSEYBSWVRWGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:368.47
Molecular Formula:C23H25LiO2Si
InChIKey:MRKCENKKRSMJIF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.644
Molecular Formula:C10H9ClN2O2
InChIKey:NCCVOQOELRREEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:428.6902
Molecular Formula:C29H48O2
InChIKey:DJTINRJHGIEFGR-AHFIXCNCSA-N
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Compound Information
Molecular Weight:460.6368
Molecular Formula:C28H32O4Si
InChIKey:OFUIRFMWORIYJF-QFIPXVFZSA-N
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Compound Information
Molecular Weight:299.3229
Molecular Formula:C13H21N3O5
InChIKey:PPDVTFAASXCNLC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:232.2353
Molecular Formula:C12H12N2O3
InChIKey:XFDAUPGSSHQRCZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.1785
Molecular Formula:C8H12O4
InChIKey:SHGLLZKGEWAIKN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:298.3331
Molecular Formula:C18H18O4
InChIKey:HVDGDHBAMCBBLR-WMLDXEAASA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:WJAVYOXZIAGPOR-FYLLDIAZSA-N
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Compound Information
Molecular Weight:241.2836
Molecular Formula:C12H19NO4
InChIKey:LAPDNEUYHHYTJQ-RKDXNWHRSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:363.547
Molecular Formula:C2F6O6S2Zn
InChIKey:CITILBVTAYEWKR-UHFFFAOYSA-L
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Compound Information
Molecular Weight:281.3077
Molecular Formula:C13H19N3O4
InChIKey:AXCJEXFAIGEXHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:197.2774
Molecular Formula:C10H19N3O
InChIKey:SUSOTOSMCXCWCQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:316.739
Molecular Formula:C16H13ClN2O3
InChIKey:GNQXXLDQTUHHBN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:309.2974
Molecular Formula:C15H20NO4P
InChIKey:GRRFDSPGTHIRLJ-KBPBESRZSA-N
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Compound Information
Molecular Weight:196.286
Molecular Formula:C12H20O2
InChIKey:QEHQCMGKZTZYRX-JFGNBEQYSA-N
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Compound Information
Molecular Weight:206.2162
Molecular Formula:C11H11FN2O
InChIKey:SKGSPHYVILRLSC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:385.3276
Molecular Formula:C18H15N3O7
InChIKey:BJBRGVFUYFTEMA-HOTGVXAUSA-N
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Compound Information
Molecular Weight:329.3505
Molecular Formula:C17H19N3O4
InChIKey:VZVVFSSCYCNAAA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:BFWWGPIXMQLRTJ-ZXFLCMHBSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:AMBOSHXMUMOHBF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:401.396
Molecular Formula:C20H24N3O4P
InChIKey:FEZMGFIYHRJBHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:KWKJNTUSCAOUBD-JTQLQIEISA-N
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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:185.2634
Molecular Formula:C10H19NO2
InChIKey:BGPZNAUOSGHIKQ-UHFFFAOYSA-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:456.7036
Molecular Formula:C29H48N2O2
InChIKey:FLZGUYUDZFBMPK-TZEXCMLFSA-N
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Compound Information
Molecular Weight:502.7703
Molecular Formula:C35H50O2
InChIKey:JRIHCZBHTGYOMV-FDMGIFJVSA-N
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Compound Information
Molecular Weight:374.775
Molecular Formula:C18H15ClN2O5
InChIKey:KVBSAYZUTWYUMA-HOTGVXAUSA-N
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