Standard Article

Light-Induced Chemistry of Oximes and Derivatives

Hydroxylamines, Oximes and Hydroxamic Acids (2010)

  1. Heinz D. Roth

Published Online: 15 SEP 2010

DOI: 10.1002/9780470682531.pat0500

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

D. Roth, H. 2010. Light-Induced Chemistry of Oximes and Derivatives. Patai's Chemistry of Functional Groups. .

Author Information

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

Photoreactions of oximes have been known for 120 years. The earliest recognized reaction was geometric isomerization, which is still the most prominent oxime photoreaction; it proceeds via a ππ* triplet state. More than sixty years later the intriguing photo-Beckmann rearrangement came to light, a C–C=N–O to O=C–N–C conversion, generating, for example, ɛ-caprolactam from cyclohexanone ξιμɛ. The rearrangement proceeds via a ππ* singlet state forming an oxazirane intermediate; the oxazirane ring usually opens in stereospecific fashion. Detailed insight into the stereo- and regiochemistry of the rearrangement was gained from steroidal oximes, the most thoroughly investigated class of oximes.

Additional photoreactions of oximes or of their ethers and esters include: net loss of hydroxylamine generating carbonyl compounds; loss of water from aldoximes forming nitriles; conversion of ketoximes to nitriles by more complex mechanisms; photochemical O–H cleavage generating iminoxyl radicals, an interesting family of free radicals; N–O cleavage giving rise to iminyl radials, which undergo radical cyclizations. β,γ-Unsaturated oximes undergo aza-di-π-methane rearrangements, cyclize to oxazolines, and undergo further reorganizations. The palette of oxime reactions has been further enriched by triplet energy transfer or electron transfer sensitization; oximes serve as electron donors or acceptors.

Keywords:

  • Light-induced chemistry of oximes and derivatives;
  • HEINZ D. ROTH;
  • E, Z isomerization;
  • photo-Beckmann rearrangement;
  • oxazirane formation;
  • O–H cleavage;
  • N–O cleavage;
  • aza-di-π-methane rearrangement;
  • isoxazoline formation;
  • iminoxyl radical;
  • iminyl radial;
  • steroidal oximes;
  • oxo-oximes

Featured Compounds

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  1. 1 - 250
Compound (E)-1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound (Z)-1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Z-2
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:OFYLBLSSPQTTHT-YVMONPNESA-N
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Compound E-2
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:OFYLBLSSPQTTHT-VMPITWQZSA-N
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Compound (E)-3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound (Z)-3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 248
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound (E)-4
Molecular Weight:199.2484
Molecular Formula:C13H13NO
InChIKey:UXILCQIEYGDOAG-GXDHUFHOSA-N
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Compound (Z)-4
Molecular Weight:199.2484
Molecular Formula:C13H13NO
InChIKey:UXILCQIEYGDOAG-UVTDQMKNSA-N
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Compound (Z)-5
Molecular Weight:161.1574
Molecular Formula:C9H7NO2
InChIKey:CWEXMSPEUDRDPH-NTMALXAHSA-N
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Compound (E)-5
Molecular Weight:161.1574
Molecular Formula:C9H7NO2
InChIKey:CWEXMSPEUDRDPH-CSKARUKUSA-N
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Compound (E)-7
Molecular Weight:255.3117
Molecular Formula:C16H17NO2
InChIKey:FERBDISQNYTXMC-WUKNDPDISA-N
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Compound (Z)-7
Molecular Weight:255.3117
Molecular Formula:C16H17NO2
InChIKey:FERBDISQNYTXMC-MSUUIHNZSA-N
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Compound 8
Molecular Weight:176.172
Molecular Formula:C9H8N2O2
InChIKey:SMHQUCTYJONECJ-KTKRTIGZSA-N
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Compound (E)-9
Molecular Weight:176.172
Molecular Formula:C9H8N2O2
InChIKey:XVDVCPOWCPQHNC-CSKARUKUSA-N
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Compound (Z)-9
Molecular Weight:176.172
Molecular Formula:C9H8N2O2
InChIKey:XVDVCPOWCPQHNC-NTMALXAHSA-N
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Compound 10
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 11
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 13
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 14
Molecular Weight:165.1891
Molecular Formula:C9H11NO2
InChIKey:XXOHMWCSTKXDLH-YFHOEESVSA-N
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Compound 15
Molecular Weight:165.1891
Molecular Formula:C9H11NO2
InChIKey:XVAIDCNLVLTVFM-UHFFFAOYSA-N
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Compound 16
Molecular Weight:113.1576
Molecular Formula:C6H11NO
InChIKey:VEZUQRBDRNJBJY-UHFFFAOYSA-N
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Compound 17
Molecular Weight:113.1576
Molecular Formula:C6H11NO
InChIKey:JBKVHLHDHHXQEQ-UHFFFAOYSA-N
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Compound 18
Molecular Weight:115.1735
Molecular Formula:C6H13NO
InChIKey:ALBYIUDWACNRRB-UHFFFAOYSA-N
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Compound 19
Molecular Weight:169.264
Molecular Formula:C10H19NO
InChIKey:XJKYDNDJFRDNHX-KKKOKTMOSA-N
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Compound 20
Molecular Weight:169.264
Molecular Formula:C10H19NO
InChIKey:XTGVNDCCKLFHJY-BDAKNGLRSA-N
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Compound 21
Molecular Weight:169.264
Molecular Formula:C10H19NO
InChIKey:PUUQDDMRHVFUDQ-BDAKNGLRSA-N
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Compound (Z)-22
Molecular Weight:187.2377
Molecular Formula:C12H13NO
InChIKey:MPGIUSCZBFKCBJ-QBFSEMIESA-N
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Compound 23
Molecular Weight:187.2377
Molecular Formula:C12H13NO
InChIKey:RHNLCMXDLOMLKY-UHFFFAOYSA-N
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Compound 24
Molecular Weight:172.2231
Molecular Formula:C12H12O
InChIKey:QIRRMISWLDWHKK-UHFFFAOYSA-N
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Compound 25
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:XHMBPLVWLSVQGQ-UHFFFAOYSA-N
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Compound 26
Molecular Weight:187.2377
Molecular Formula:C12H13NO
InChIKey:IKAGAKULMNUAJU-UHFFFAOYSA-N
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Compound (E)-22
Molecular Weight:187.2377
Molecular Formula:C12H13NO
InChIKey:MPGIUSCZBFKCBJ-ACCUITESSA-N
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Compound 27
Molecular Weight:161.2004
Molecular Formula:C10H11NO
InChIKey:OGVPVEBIPIJKEJ-MFDVASPDSA-N
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Compound (E)-29
Molecular Weight:161.2004
Molecular Formula:C10H11NO
InChIKey:LGHWILJMCJJDMV-FPLPWBNLSA-N
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Compound (Z)-29
Molecular Weight:161.2004
Molecular Formula:C10H11NO
InChIKey:LGHWILJMCJJDMV-FPLPWBNLSA-N
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Compound 30
Molecular Weight:113.1576
Molecular Formula:C6H11NO
InChIKey:NELACHBDCVNKTB-UHFFFAOYSA-N
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Compound 32
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:NCCHARWOCKOHIH-UHFFFAOYSA-N
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Compound 31
Molecular Weight:135.1632
Molecular Formula:C8H9NO
InChIKey:GDAZZZLHHSQPOQ-UHFFFAOYSA-N
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Compound 33
Molecular Weight:401.6682
Molecular Formula:C27H47NO
InChIKey:JDISBUOUHRAUBW-ZXDWHPMWSA-N
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Compound 34
Molecular Weight:401.6682
Molecular Formula:C27H47NO
InChIKey:MPOOJUCLYWRBKH-GRFPRMRASA-N
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Compound 35
Molecular Weight:401.6682
Molecular Formula:C27H47NO
InChIKey:KFJNEFBBGCKUAS-HVPCJGPWSA-N
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Compound 36a
Molecular Weight:197.2325
Molecular Formula:C13H11NO
InChIKey:DNYZBFWKVMKMRM-UHFFFAOYSA-N
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Compound 36b
Molecular Weight:211.2591
Molecular Formula:C14H13NO
InChIKey:MFZNRFQCOCWADL-UHFFFAOYSA-N
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Compound 36
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 39
Molecular Weight:327.4605
Molecular Formula:C21H29NO2
InChIKey:IYBUCRWPJZEIGJ-IZTFOULLSA-N
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Compound 38
Molecular Weight:345.4757
Molecular Formula:C21H31NO3
InChIKey:VZJWDAYDJDYHKS-YSTMREEHSA-N
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Compound 40
Molecular Weight:177.2429
Molecular Formula:C11H15NO
InChIKey:OMGYRVZNACAWDS-FMIVXFBMSA-N
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Compound 41
Molecular Weight:176.235
Molecular Formula:C11H14NO
InChIKey:OMGYRVZNACAWDS-FMIVXFBMSA-N
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Compound 42
Molecular Weight:103.1213
Molecular Formula:C7H5N
InChIKey:JFDZBHWFFUWGJE-UHFFFAOYSA-N
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Compound (E)-43
Molecular Weight:369.4971
Molecular Formula:C23H31NO3
InChIKey:VWPVLBMFEWIEJW-NRWXAJLOSA-N
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Compound 44
Molecular Weight:369.4971
Molecular Formula:C23H31NO3
InChIKey:NOETVJARAGJNRP-GUYYSMISSA-N
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Compound 43
Molecular Weight:371.513
Molecular Formula:C23H33NO3
InChIKey:OUOGHZIOSYXOFF-UFHIKBBASA-N
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Compound 45
Molecular Weight:285.4238
Molecular Formula:C19H27NO
InChIKey:ILEACKBEHDIYIN-QKBRSHRXSA-N
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Compound 46
Molecular Weight:285.4238
Molecular Formula:C19H27NO
InChIKey:MGQPYJMVJDEJRO-WFZCBACDSA-N
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Compound (E,E)-27
Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:JSCPGPKWAGKQKA-CDKJVOIVSA-N
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Compound (Z,E)-27
Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:JSCPGPKWAGKQKA-ZLNDROGTSA-N
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Compound (E,Z)-27
Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:JSCPGPKWAGKQKA-LVQHWDRTSA-N
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Compound (Z,Z)-27
Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:JSCPGPKWAGKQKA-DMGFJBLZSA-N
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Compound 47
Molecular Weight:291.4714
Molecular Formula:C19H33NO
InChIKey:UAKZDDFHGIVEID-HMMYKYKNSA-N
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Compound 49
Molecular Weight:273.4561
Molecular Formula:C19H31N
InChIKey:MQMKNDOEWLDTSA-JOBJLJCHSA-N
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Compound 50
Molecular Weight:273.4561
Molecular Formula:C19H31N
InChIKey:CUPTWQLCJWWWMT-UHFFFAOYSA-N
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Compound 51
Molecular Weight:305.498
Molecular Formula:C20H35NO
InChIKey:FYXNTJDWAPUJSZ-HVCKESBWSA-N
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Compound (E,E)-52
Molecular Weight:235.3651
Molecular Formula:C15H25NO
InChIKey:LWMOQGBYLMTRNL-FVTBZGPOSA-N
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Compound (E,Z)-52
Molecular Weight:235.3651
Molecular Formula:C15H25NO
InChIKey:LWMOQGBYLMTRNL-FVTBZGPOSA-N
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Compound (Z,E)-53
Molecular Weight:235.3651
Molecular Formula:C15H25NO
InChIKey:QUUKFCINMRGSGI-GOAZRFPBSA-N
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Compound 54
Molecular Weight:147.1739
Molecular Formula:C9H9NO
InChIKey:IQYQPCRTUUEMKC-KTKRTIGZSA-N
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Compound 56
Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:GMNPPKWGHKAQSX-XFXZXTDPSA-N
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Compound 58
Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:VUHWNMVPFXVDBB-UHFFFAOYSA-N
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Compound 59
Molecular Weight:189.2536
Molecular Formula:C12H15NO
InChIKey:RMTQFMGNJYXJMG-RAXLEYEMSA-N
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Compound 60
Molecular Weight:189.2536
Molecular Formula:C12H15NO
InChIKey:OMJMCDKFIPGGBI-LCYFTJDESA-N
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Compound 61
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 62
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 63
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 64
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 67
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 68
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 69
Molecular Weight:189.2536
Molecular Formula:C12H15NO
InChIKey:YYOCSURFYGZXHJ-UKTHLTGXSA-N
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Compound 72
Molecular Weight:189.2536
Molecular Formula:C12H15NO
InChIKey:KAZYKWOYTCEMFD-UKTHLTGXSA-N
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Compound 74
Molecular Weight:201.2643
Molecular Formula:C13H15NO
InChIKey:WDLUBGBHNKTVEZ-WYMLVPIESA-N
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Compound 73
Molecular Weight:215.2909
Molecular Formula:C14H17NO
InChIKey:VSVMYULMDBHCKK-XNTDXEJSSA-N
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Compound 75
Molecular Weight:305.3704
Molecular Formula:C20H19NO2
InChIKey:CWFNRHOQFQNWDJ-RCCKNPSSSA-N
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Compound 77
Molecular Weight:245.3184
Molecular Formula:C18H15N
InChIKey:AHQNTOAHHXDTKL-UHFFFAOYSA-N
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Compound 76
Molecular Weight:305.3704
Molecular Formula:C20H19NO2
InChIKey:QIDNJBDZYPXKCY-KGENOOAVSA-N
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Compound 79
Molecular Weight:305.3704
Molecular Formula:C20H21NO2
InChIKey:CIRHFEMZSLWNEM-BMRADRMJSA-N
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Compound 80
Molecular Weight:305.3704
Molecular Formula:C20H21NO2
InChIKey:WNSAZGROGDERMF-UHFFFAOYSA-N
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Compound 81
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 82
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 83
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 84
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 85
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 86
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 87
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 88
Molecular Weight:195.2597
Molecular Formula:C14H13N
InChIKey:RQJJERLPNPDQLD-UHFFFAOYSA-N
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Compound 90
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 91a
Molecular Weight:203.2802
Molecular Formula:C13H17NO
InChIKey:QARJRTSXCQPTAV-QDCWQMMGSA-N
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Compound 92a
Molecular Weight:203.2802
Molecular Formula:C13H17NO
InChIKey:JWOHTQURBIQXKO-NTEUORMPSA-N
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Compound 91b
Molecular Weight:279.3761
Molecular Formula:C19H21NO
InChIKey:COLOYAJBOOZODI-HMMYKYKNSA-N
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Compound 91
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 92
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 92b
Molecular Weight:279.3761
Molecular Formula:C19H21NO
InChIKey:WUINDACJQDKYJR-XSFVSMFZSA-N
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Compound 95
Molecular Weight:455.5497
Molecular Formula:C31H25N3O
InChIKey:PUSPGCDTTOIAEH-JIRKWGMCSA-N
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Compound 96
Molecular Weight:217.3068
Molecular Formula:C14H19NO
InChIKey:GCKLNTXYXFAAEQ-GCHFJXRNSA-N
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Compound 98
Molecular Weight:401.5438
Molecular Formula:C26H31N3O
InChIKey:UWTOKDQIOBRIBJ-MUFRIFMGSA-N
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Compound 97
Molecular Weight:217.3068
Molecular Formula:C14H19NO
InChIKey:BVVXUABUUSJJQS-XNTDXEJSSA-N
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Compound 101
Molecular Weight:483.5996
Molecular Formula:C34H29NO2
InChIKey:NJHZYKHYFKPRTN-XICOUIIWSA-N
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Compound 102
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 103
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 104
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 105
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 106
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 108
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 109
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 110
Molecular Weight:196.2656
Molecular Formula:C11H17NO2
InChIKey:ISAIIPOKTBSBHP-IUZMTQGWSA-O
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Compound 111
Molecular Weight:195.2582
Molecular Formula:C11H17NO2
InChIKey:DPRRISQSEVKKOT-YHMJZVADSA-N
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Compound 112
Molecular Weight:250.3382
Molecular Formula:C17H18N2
InChIKey:NGVXFRHGMCHOHJ-UHFFFAOYSA-N
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Compound 113
Molecular Weight:125.1683
Molecular Formula:C7H11NO
InChIKey:RPGSLIJSBHTVPW-FPLPWBNLSA-N
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Compound 114
Molecular Weight:125.1683
Molecular Formula:C7H11NO
InChIKey:WXPIMQINWWWSEF-UHFFFAOYSA-N
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Compound 115
Molecular Weight:125.1683
Molecular Formula:C7H11NO
InChIKey:VIJCSXWSAGILRP-UHFFFAOYSA-N
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Compound 116
Molecular Weight:127.1842
Molecular Formula:C7H13NO
InChIKey:OXRCIXHTUHZNRY-UHFFFAOYSA-N
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Compound 117
Molecular Weight:127.1842
Molecular Formula:C7H13NO
InChIKey:ZYFCJOQNKMJDJQ-NTSWFWBYSA-N
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Compound 118
Molecular Weight:167.2481
Molecular Formula:C10H17NO
InChIKey:POYGWXWGOBEMAT-FLIBITNWSA-N
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Compound 119
Molecular Weight:167.2481
Molecular Formula:C10H17NO
InChIKey:JQQOCAUUPQUUEK-UHFFFAOYSA-N
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Compound 120
Molecular Weight:167.2481
Molecular Formula:C10H17NO
InChIKey:PBWHMIKVKLPBCY-UHFFFAOYSA-N
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Compound 121
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 122
Molecular Weight:167.2481
Molecular Formula:C10H17NO
InChIKey:OVFDEGGJFJECAT-NTIVIHFJSA-N
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Compound 123
Molecular Weight:167.2481
Molecular Formula:C10H17NO
InChIKey:RLZHPSSARXFRJU-UHFFFAOYSA-N
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Compound 124
Molecular Weight:164.2872
Molecular Formula:C12H20
InChIKey:JTICILNLZKBRFP-UHFFFAOYSA-N
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Compound 125
Molecular Weight:138.2499
Molecular Formula:C10H18
InChIKey:RIIDDPWESWWOEQ-UHFFFAOYSA-N
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Compound 126
Molecular Weight:165.2322
Molecular Formula:C10H15NO
InChIKey:RABVIFXMFZFITE-KHPPLWFESA-N
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Compound 127
Molecular Weight:165.2322
Molecular Formula:C10H15NO
InChIKey:OKDJIRNQPPBDKJ-UHFFFAOYSA-N
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Compound 128
Molecular Weight:147.2169
Molecular Formula:C10H13N
InChIKey:HSKASOUJOUMXNC-UHFFFAOYSA-N
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Compound (E)-180
Molecular Weight:209.2848
Molecular Formula:C12H19NO2
InChIKey:BINOREILBYKSMZ-UKTHLTGXSA-N
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Compound 129
Molecular Weight:303.4391
Molecular Formula:C19H29NO2
InChIKey:CCDNGLFWWXCDAW-QBDCATRVSA-N
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Compound 130
Molecular Weight:371.513
Molecular Formula:C23H33NO3
InChIKey:OUOGHZIOSYXOFF-UFHIKBBASA-N
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Compound (Z)-43
Molecular Weight:369.4971
Molecular Formula:C23H31NO3
InChIKey:VWPVLBMFEWIEJW-NRWXAJLOSA-N
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Compound 131
Molecular Weight:399.6523
Molecular Formula:C27H45NO
InChIKey:QNTASHOAVRSLMD-SIWSWZRQSA-N
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Compound 132
Molecular Weight:399.6523
Molecular Formula:C27H45NO
InChIKey:QNTASHOAVRSLMD-SIWSWZRQSA-N
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Compound 133
Molecular Weight:399.6523
Molecular Formula:C27H45NO
InChIKey:QNTASHOAVRSLMD-SIWSWZRQSA-N
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Compound 134
Molecular Weight:397.6364
Molecular Formula:C27H43NO
InChIKey:KCIUAAYYHVRWSB-SIWSWZRQSA-N
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Compound 135
Molecular Weight:399.6523
Molecular Formula:C27H45NO
InChIKey:SHVBKGHOYCELLZ-HBQJLUOTSA-N
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Compound 136
Molecular Weight:399.6523
Molecular Formula:C27H45NO
InChIKey:WLRKZCOQKNBQFB-CIKOVIBGSA-N
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Compound 137
Molecular Weight:399.6523
Molecular Formula:C27H45NO
InChIKey:UKGGIXPTRIZOOU-DILNCBNMSA-N
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Compound 138
Molecular Weight:347.4916
Molecular Formula:C21H33NO3
InChIKey:MAIMKJVHBJVMBS-NJEVLBSVSA-N
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Compound 139
Molecular Weight:347.4916
Molecular Formula:C21H33NO3
InChIKey:WCLNQJVUMYGHJY-ODVAYUMLSA-N
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Compound 140
Molecular Weight:347.4916
Molecular Formula:C21H33NO3
InChIKey:VYPOZWWTWYUODO-ODVAYUMLSA-N
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Compound 141
Molecular Weight:347.4916
Molecular Formula:C21H33NO3
InChIKey:MAIMKJVHBJVMBS-ALOREAFYSA-N
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Compound 142
Molecular Weight:347.4916
Molecular Formula:C21H33NO3
InChIKey:WCLNQJVUMYGHJY-DHDYLUHWSA-N
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Compound 143
Molecular Weight:347.4916
Molecular Formula:C21H33NO3
InChIKey:WCLNQJVUMYGHJY-ODVAYUMLSA-N
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Compound 144
Molecular Weight:275.429
Molecular Formula:C18H29NO
InChIKey:KUZXGUHOIFGBJU-LBMPELRMSA-N
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Compound 145
Molecular Weight:257.4137
Molecular Formula:C18H27N
InChIKey:QPQKLISGQNVASL-ASZWDNHYSA-N
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Compound 146
Molecular Weight:257.4137
Molecular Formula:C18H27N
InChIKey:FZPBHDNFGJZVOC-ASZWDNHYSA-N
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Compound 147
Molecular Weight:289.4555
Molecular Formula:C19H31NO
InChIKey:RHGVUBJZUJLKOQ-ONBNRTMESA-N
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Compound 148
Molecular Weight:275.429
Molecular Formula:C18H29NO
InChIKey:RAYHDFBLAPPFCZ-SSJNANRASA-N
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Compound 149
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 155
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 150
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 156
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 151
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 153
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 152
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 154
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 157
Molecular Weight:400.6585
Molecular Formula:C27H45NO
InChIKey:Not Available
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Compound 159
Molecular Weight:400.6585
Molecular Formula:C27H45NO
InChIKey:Not Available
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Compound 161
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 158
Molecular Weight:432.7003
Molecular Formula:C28H49NO2
InChIKey:Not Available
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Compound 160
Molecular Weight:431.6942
Molecular Formula:C28H49NO2
InChIKey:LSACMXITTOJWEQ-WAGWGTPRSA-N
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Compound 162
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 164
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 163
Molecular Weight:402.6708
Molecular Formula:C27H45NO
InChIKey:Not Available
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Compound 166
Molecular Weight:402.6708
Molecular Formula:C27H45NO
InChIKey:Not Available
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Compound 167
Molecular Weight:413.6789
Molecular Formula:C28H47NO
InChIKey:ORMKERCTGBESMN-YFFBDUEJSA-N
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Compound 168
Molecular Weight:413.6789
Molecular Formula:C28H47NO
InChIKey:ORMKERCTGBESMN-YFFBDUEJSA-N
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Compound 169
Molecular Weight:413.6789
Molecular Formula:C28H47NO
InChIKey:LJEVPNGUITXBRZ-URBFCUMZSA-N
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Compound 170
Molecular Weight:415.6924
Molecular Formula:C28H48NO
InChIKey:Not Available
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Compound 171
Molecular Weight:427.7055
Molecular Formula:C29H49NO
InChIKey:JRODMKQNKJCYHF-SSAOKAMWSA-N
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Compound 172
Molecular Weight:427.7055
Molecular Formula:C29H49NO
InChIKey:IKDAWDHOUFVSCC-KOVCEZANSA-N
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Compound 173
Molecular Weight:427.7055
Molecular Formula:C29H49NO
InChIKey:GLNLVJXHAUPFAU-KOVCEZANSA-N
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Compound (E)-174
Molecular Weight:129.157
Molecular Formula:C6H11NO2
InChIKey:ABZLRXBAERZNRD-FNORWQNLSA-N
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Compound (Z)-174
Molecular Weight:129.157
Molecular Formula:C6H11NO2
InChIKey:ABZLRXBAERZNRD-ALCCZGGFSA-N
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Compound 175
Molecular Weight:199.2899
Molecular Formula:C11H21NO2
InChIKey:GWRCDWZIQSBOJI-ZRDIBKRKSA-N
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Compound (Z)-177
Molecular Weight:199.2899
Molecular Formula:C11H21NO2
InChIKey:QYLSDOPORONFRN-XFXZXTDPSA-N
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Compound 176
Molecular Weight:199.2899
Molecular Formula:C11H21NO2
InChIKey:FXLIFYYTJLMADD-ZRDIBKRKSA-N
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Compound (E)-177
Molecular Weight:199.2899
Molecular Formula:C11H21NO2
InChIKey:QYLSDOPORONFRN-FMIVXFBMSA-N
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Compound 178
Molecular Weight:84.0965
Molecular Formula:C4H6NO
InChIKey:UGQVJNSXZWLJMP-UHFFFAOYSA-N
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Compound 179
Molecular Weight:127.1412
Molecular Formula:C6H9NO2
InChIKey:SROSLIALPCZMCB-DAXSKMNVSA-N
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Compound 184
Molecular Weight:136.2142
Molecular Formula:C9H14N
InChIKey:ZNWLWFRMPJDTEW-BRFYHDHCSA-N
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Compound 185
Molecular Weight:135.2062
Molecular Formula:C9H13N
InChIKey:JUTJFQIFRWSPFI-MRVPVSSYSA-N
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Compound 186
Molecular Weight:135.2062
Molecular Formula:C9H13N
InChIKey:IMCLYKLRSANTMV-MRVPVSSYSA-N
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Compound 187
Molecular Weight:137.2221
Molecular Formula:C9H15N
InChIKey:ZNWLWFRMPJDTEW-BRFYHDHCSA-N
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Compound 181
Molecular Weight:209.2848
Molecular Formula:C12H19NO2
InChIKey:SVMXJNPMMRYVFW-UHFFFAOYSA-N
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Compound 182
Molecular Weight:164.2243
Molecular Formula:C10H14NO
InChIKey:GNGDLNMVJARTRQ-SCZZXKLOSA-N
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Compound (Z)-180
Molecular Weight:209.2848
Molecular Formula:C12H19NO2
InChIKey:BINOREILBYKSMZ-LCYFTJDESA-N
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Compound 183
Molecular Weight:209.2848
Molecular Formula:C12H19NO2
InChIKey:AXYIADQAIZHKQV-SKDRFNHKSA-N
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Compound (E)-188
Molecular Weight:211.3006
Molecular Formula:C12H21NO2
InChIKey:DFZPTACRIAQCIW-ACCUITESSA-N
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Compound (Z)-188
Molecular Weight:211.3006
Molecular Formula:C12H21NO2
InChIKey:DFZPTACRIAQCIW-QBFSEMIESA-N
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Compound 189
Molecular Weight:211.3006
Molecular Formula:C12H21NO2
InChIKey:MQEUSTJIAUITKJ-ACCUITESSA-N
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Compound 190
Molecular Weight:211.3006
Molecular Formula:C12H21NO2
InChIKey:GNJQNZNVEFOKBH-ACCUITESSA-N
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Compound 191a
Molecular Weight:211.3006
Molecular Formula:C12H21NO2
InChIKey:MHNQEZJGZJFBKI-UHFFFAOYSA-N
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Compound 191b
Molecular Weight:193.2854
Molecular Formula:C12H19NO
InChIKey:YNXXCUKUDONOEW-UHFFFAOYSA-N
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Compound 191c
Molecular Weight:198.3019
Molecular Formula:C12H22O2
InChIKey:KISVAASFGZJBCY-UHFFFAOYSA-N
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Compound 192
Molecular Weight:193.2854
Molecular Formula:C12H19NO
InChIKey:JXLKEPJGAGPQES-UHFFFAOYSA-N
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Compound 191
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 193
Molecular Weight:193.2854
Molecular Formula:C12H19NO
InChIKey:ZNFVMOGGTZSTSS-UHFFFAOYSA-N
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Compound 194
Molecular Weight:211.3006
Molecular Formula:C12H21NO2
InChIKey:YKHZGLKQBYTRHO-UHFFFAOYSA-N
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Compound 195a
Molecular Weight:183.2475
Molecular Formula:C10H17NO2
InChIKey:GYIRKYIYBKUPHN-XFFZJAGNSA-N
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Compound 195b
Molecular Weight:197.2741
Molecular Formula:C11H19NO2
InChIKey:KWJSKQSDPQAPLS-XYOKQWHBSA-N
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Compound 195c
Molecular Weight:211.3006
Molecular Formula:C12H21NO2
InChIKey:OWQQEPNYFSGBDM-UKTHLTGXSA-N
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Compound 200
Molecular Weight:199.2899
Molecular Formula:C11H21NO2
InChIKey:NEXYHSLSLXTQQH-WQLSENKSSA-N
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Compound 195
Molecular Weight:Not Available
Molecular Formula:(CH2)nC9H15NO2
InChIKey:GYIRKYIYBKUPHN-XFFZJAGNSA-N
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Compound 196
Molecular Weight:Not Available
Molecular Formula:(CH2)nC8H12NO
InChIKey:GZCZLFQYPXQWMY-UHFFFAOYSA-N
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Compound 197
Molecular Weight:Not Available
Molecular Formula:(CH2)nC8H12NO
InChIKey:DAKLBJUAXLFIJD-UHFFFAOYSA-N
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Compound 198
Molecular Weight:Not Available
Molecular Formula:(CH2)nC7H12N
InChIKey:FSKRSJMYNXGUBM-UHFFFAOYSA-N
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Compound 196a
Molecular Weight:152.2136
Molecular Formula:C9H14NO
InChIKey:GZCZLFQYPXQWMY-UHFFFAOYSA-N
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Compound 196b
Molecular Weight:166.2401
Molecular Formula:C10H16NO
InChIKey:LCZOZOFRWZGKOJ-UHFFFAOYSA-N
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Compound 196c
Molecular Weight:180.2667
Molecular Formula:C11H18NO
InChIKey:HEAVLKSDIJHFAY-UHFFFAOYSA-N
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Compound 197a
Molecular Weight:152.2136
Molecular Formula:C9H14NO
InChIKey:DAKLBJUAXLFIJD-UHFFFAOYSA-N
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Compound 197b
Molecular Weight:166.2401
Molecular Formula:C10H16NO
InChIKey:DDDNQMOGIANBLW-UHFFFAOYSA-N
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Compound 197c
Molecular Weight:180.2667
Molecular Formula:C11H18NO
InChIKey:NSWNSRSEJBTFOS-UHFFFAOYSA-N
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Compound 198a
Molecular Weight:124.2035
Molecular Formula:C8H14N
InChIKey:FSKRSJMYNXGUBM-UHFFFAOYSA-N
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Compound 198b
Molecular Weight:138.23
Molecular Formula:C9H16N
InChIKey:TTWPISKVNKXMPJ-UHFFFAOYSA-N
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Compound 198c
Molecular Weight:152.2566
Molecular Formula:C10H18N
InChIKey:RWQCBHHFGMJQNL-UHFFFAOYSA-N
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Compound 199
Molecular Weight:138.23
Molecular Formula:C9H16N
InChIKey:KSOQPAIMKVRQQA-UHFFFAOYSA-N
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Compound 201
Molecular Weight:168.256
Molecular Formula:C10H18NO
InChIKey:DERAWIHHQPARRN-UHFFFAOYSA-N
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Compound (E)-202
Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:RMBCFTXUYGHXFN-DHZHZOJOSA-N
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Compound 204
Molecular Weight:326.4326
Molecular Formula:C20H26N2O2
InChIKey:HVNYESPPKCHVJQ-QURGRASLSA-N
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Compound 203
Molecular Weight:162.2084
Molecular Formula:C10H12NO
InChIKey:LNKQHVCWOHPGIU-UHFFFAOYSA-N
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Compound 205
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 205a
Molecular Weight:193.2423
Molecular Formula:C11H15NO2
InChIKey:KVTVPYFNRPPSIW-XFXZXTDPSA-N
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Compound 205b
Molecular Weight:193.2423
Molecular Formula:C11H15NO2
InChIKey:SHNOIIHQFACZOS-XFXZXTDPSA-N
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Compound 206
Molecular Weight:249.3486
Molecular Formula:C15H23NO2
InChIKey:GDAGJNIKLAINHL-VBKFSLOCSA-N
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Compound 207
Molecular Weight:249.3486
Molecular Formula:C15H23NO2
InChIKey:DXLHNODUOBPLLT-WJDWOHSUSA-N
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Compound 208
Molecular Weight:249.3486
Molecular Formula:C15H23NO2
InChIKey:DXLHNODUOBPLLT-WJDWOHSUSA-N
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Compound 209
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 210
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 212
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 211
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 251
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 213
Molecular Weight:137.136
Molecular Formula:C7H7NO2
InChIKey:ORIHZIZPTZTNCU-VMPITWQZSA-N
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Compound 214
Molecular Weight:119.1207
Molecular Formula:C7H5NO
InChIKey:Not Available
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Compound 215
Molecular Weight:119.1207
Molecular Formula:C7H5NO
InChIKey:CHZCERSEMVWNHL-UHFFFAOYSA-N
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Compound 216
Molecular Weight:151.1626
Molecular Formula:C8H9NO2
InChIKey:JZXBPZWZZOXDFB-TWGQIWQCSA-N
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Compound 217
Molecular Weight:133.1473
Molecular Formula:C8H7NO
InChIKey:GAUKCDPSYQUYQL-UHFFFAOYSA-N
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Compound 218
Molecular Weight:133.1473
Molecular Formula:C8H7NO
InChIKey:DQSHFKPKFISSNM-UHFFFAOYSA-N
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Compound 219
Molecular Weight:237.2964
Molecular Formula:C16H15NO
InChIKey:DEKOOXQBPCOQQX-RFTYBOQRSA-N
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Compound 221a
Molecular Weight:219.2811
Molecular Formula:C16H13N
InChIKey:LBDODDLWQDVLIH-UHFFFAOYSA-N
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Compound 221
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 220
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound (Z)-219
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 219a
Molecular Weight:237.2964
Molecular Formula:C16H15NO
InChIKey:DEKOOXQBPCOQQX-OHCYLCFFSA-N
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