Standard Article

Conjugate Addition of Hydroxylamines, Oximes and Hydroxamic Acids

Hydroxylamines, Oximes and Hydroxamic Acids (2010)

  1. Yunfei Du,
  2. Deng Mao,
  3. Daisy Zhang-Negrerie,
  4. Kang Zhao

Published Online: 15 SEP 2010

DOI: 10.1002/9780470682531.pat0501

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Du, Y., Mao, D., Zhang-Negrerie, D. and Zhao, K. 2010. Conjugate Addition of Hydroxylamines, Oximes and Hydroxamic Acids. Patai's Chemistry of Functional Groups. .

Author Information

  1. School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, Nankai District, P. R. China

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

  • 1
    General Introduction
  • 2
    Conjugate Addition of Hydroxylamine and Itsderivatives
  • 3
    Conjugate Addition of Oximes
  • 4
    Conjugate Addition of Hydroxamic Acids
  • 5
    Conclusions
  • 6
    Acknowledgments

The conjugate addition of hydroxylamines, oximes and hydroxamic acids provides convenient route to incorporate an N[BOND]O moiety into various Michael acceptors. This chapter reviews comprehensive experimental reactions on the formation of carbon–nitrogen and carbon–oxygen bonds via conjugate addition of hydroxylamines, oximes and hydroxamic acids to alkenes, alkynes or allenes attached to one or more electron-withdrawing groups. Hydroxylamine derivatives predominantly undergo N-centered conjugate addition, while for the ambient nucleophilic oximes and hydroxamic acids, both N-centered and O-centered conjugate addition are operative by control of the reaction conditions. A concerted cycloaddition mechanism has been well established for the conjugate addition of N-substituted hydroxylamines. The last decade has witnessed enormous growth in enantioselective conjugate addition of hydroxylamine derivatives and the O-centered oximes.

Keywords:

  • Conjugate addition, Hydroxylamines, Oximes, Hydroxamic acids, 1,4-Adducts, Michael acceptor, Concerted cycloaddition, Asymmetric conjugate addition, Nitrone

Featured Compounds

VIEW

  1. 1 - 250
Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 4
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 5
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:BAPJBEWLBFYGME-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 6
Molecular Weight:205.2084
Molecular Formula:C8H15NO5
InChIKey:NNVNNJSBWGOCGI-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 7
Molecular Weight:118.154
Molecular Formula:C4H6O2S
InChIKey:AFOSIXZFDONLBT-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 8
Molecular Weight:151.184
Molecular Formula:C4H9NO3S
InChIKey:LSPITPXGBBVDQS-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 9
Molecular Weight:148.1586
Molecular Formula:C9H8O2
InChIKey:WBYWAXJHAXSJNI-VOTSOKGWSA-N
View compound in article | Full details | Search for this compound
Compound 10
Molecular Weight:181.1885
Molecular Formula:C9H11NO3
InChIKey:MUURQVSFSDVWKM-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 11
Molecular Weight:165.1891
Molecular Formula:C9H11NO2
InChIKey:UJOYFRCOTPUKAK-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 12
Molecular Weight:234.271
Molecular Formula:C12H10O3S
InChIKey:DYURULMVVUWNMX-VQHVLOKHSA-N
View compound in article | Full details | Search for this compound
Compound 13
Molecular Weight:267.301
Molecular Formula:C12H13NO4S
InChIKey:AADFGRCXZWIGOR-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 14
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 16
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 17
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:MTZWHHIREPJPTG-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 18
Molecular Weight:171.2368
Molecular Formula:C9H17NO2
InChIKey:YUARUBGPNUEQBK-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 20
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:UNELZWLTCBQRGC-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 21
Molecular Weight:141.1677
Molecular Formula:C7H11NO2
InChIKey:IHBAYRYWEQNTGU-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 22
Molecular Weight:248.183
Molecular Formula:C9H14BrNS
InChIKey:HHUKIIGNMPCJSJ-HJWRWDBZSA-N
View compound in article | Full details | Search for this compound
Compound 23
Molecular Weight:200.301
Molecular Formula:C9H16N2OS
InChIKey:DPJUWADAMFBNKZ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 24
Molecular Weight:65.0733
Molecular Formula:C4H3N
InChIKey:IRLQAJPIHBZROB-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 25
Molecular Weight:98.1032
Molecular Formula:C4H6N2O
InChIKey:FNXYWHTZDAVRTB-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 26
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 27
Molecular Weight:241.2851
Molecular Formula:C15H15NO2
InChIKey:MXHKSTBYXCKUQJ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 28
Molecular Weight:256.2997
Molecular Formula:C15H16N2O2
InChIKey:ZUWXMDDZLGXBOF-ICFOKQHNSA-N
View compound in article | Full details | Search for this compound
Compound 29
Molecular Weight:223.2698
Molecular Formula:C15H13NO
InChIKey:IXQYPXRYRSEMAA-AQVAVHIYSA-N
View compound in article | Full details | Search for this compound
Compound 30
Molecular Weight:290.316
Molecular Formula:C18H14N2O2
InChIKey:URZSQKTVRXTQTQ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 31
Molecular Weight:143.1406
Molecular Formula:C6H9NO3
InChIKey:WZCQFOAUTDONOT-SREVYHEPSA-N
View compound in article | Full details | Search for this compound
Compound 32
Molecular Weight:125.1253
Molecular Formula:C6H7NO2
InChIKey:KYVXYWKQFCSMHL-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 33a
Molecular Weight:352.499
Molecular Formula:C21H24O3Si
InChIKey:WSMXUZXPKHTNPA-SFHVURJKSA-N
View compound in article | Full details | Search for this compound
Compound 33b
Molecular Weight:114.0993
Molecular Formula:C5H6O3
InChIKey:AWNLUIGMHSSXHB-BYPYZUCNSA-N
View compound in article | Full details | Search for this compound
Compound 34a
Molecular Weight:459.652
Molecular Formula:C28H33NO3Si
InChIKey:MZQPYKYDOGADPI-RRPNLBNLSA-N
View compound in article | Full details | Search for this compound
Compound 34b
Molecular Weight:221.2524
Molecular Formula:C12H15NO3
InChIKey:JKNNXLJRYMHHPE-WDEREUQCSA-N
View compound in article | Full details | Search for this compound
Compound 33c
Molecular Weight:228.3602
Molecular Formula:C11H20O3Si
InChIKey:OBEODKRPVKJAIX-VIFPVBQESA-N
View compound in article | Full details | Search for this compound
Compound 34c
Molecular Weight:351.5127
Molecular Formula:C18H29NO4Si
InChIKey:CDVDOGNLNOBZOG-JKSUJKDBSA-N
View compound in article | Full details | Search for this compound
Compound 33
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 34
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 189
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 49
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 35
Molecular Weight:161.1989
Molecular Formula:C7H15NO3
InChIKey:NGEFAIKVNAUJKX-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 36
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 64a
Molecular Weight:176.2118
Molecular Formula:C11H12O2
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 38
Molecular Weight:177.1998
Molecular Formula:C10H11NO2
InChIKey:NUIOEYZFQWGTEJ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 39
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 40
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 41
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 42
Molecular Weight:228.3602
Molecular Formula:C11H20O3Si
InChIKey:OBEODKRPVKJAIX-SECBINFHSA-N
View compound in article | Full details | Search for this compound
Compound 43
Molecular Weight:275.4167
Molecular Formula:C12H25NO4Si
InChIKey:KHIWWTPBIJAUSZ-VHSXEESVSA-N
View compound in article | Full details | Search for this compound
Compound 44
Molecular Weight:275.4167
Molecular Formula:C12H25NO4Si
InChIKey:OHGLYPRTZYGWKH-AXDSSHIGSA-N
View compound in article | Full details | Search for this compound
Compound 45
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 47
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 48
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 50a
Molecular Weight:205.253
Molecular Formula:C12H15NO2
InChIKey:MIIOWIOMHHFJGC-YHMJZVADSA-N
View compound in article | Full details | Search for this compound
Compound 50b
Molecular Weight:205.253
Molecular Formula:C12H15NO2
InChIKey:MIIOWIOMHHFJGC-RGURZIINSA-N
View compound in article | Full details | Search for this compound
Compound 51
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 51a
Molecular Weight:285.3361
Molecular Formula:C14H23NO5
InChIKey:YSNYRLFAMVTFTM-QROSGCPLSA-N
View compound in article | Full details | Search for this compound
Compound 51b
Molecular Weight:483.6719
Molecular Formula:C27H37NO5Si
InChIKey:DIDNGOZXJCUDMO-XDSRXIPYSA-N
View compound in article | Full details | Search for this compound
Compound 53
Molecular Weight:323.4287
Molecular Formula:C21H25NO2
InChIKey:JKYVHNGUIMNYCY-JJJPLKNQSA-N
View compound in article | Full details | Search for this compound
Compound 54a
Molecular Weight:324.4168
Molecular Formula:C20H24N2O2
InChIKey:CEWYABPZPDHRCB-LPHOPBHVSA-N
View compound in article | Full details | Search for this compound
Compound anti-52a
Molecular Weight:408.4886
Molecular Formula:C21H32N2O6
InChIKey:UYDNAUOUURGUGL-SJORKVTESA-N
View compound in article | Full details | Search for this compound
Compound anti-52b
Molecular Weight:606.8243
Molecular Formula:C34H46N2O6Si
InChIKey:QVYDZXQXPRTQKB-XZWHSSHBSA-N
View compound in article | Full details | Search for this compound
Compound syn-52a
Molecular Weight:408.4886
Molecular Formula:C21H32N2O6
InChIKey:UYDNAUOUURGUGL-IRXDYDNUSA-N
View compound in article | Full details | Search for this compound
Compound syn-52b
Molecular Weight:606.8243
Molecular Formula:C34H46N2O6Si
InChIKey:QVYDZXQXPRTQKB-KYJUHHDHSA-N
View compound in article | Full details | Search for this compound
Compound 54b
Molecular Weight:324.4168
Molecular Formula:C20H24N2O2
InChIKey:CEWYABPZPDHRCB-QFBILLFUSA-N
View compound in article | Full details | Search for this compound
Compound 55
Molecular Weight:201.2212
Molecular Formula:C12H11NO2
InChIKey:GYAPIMIROZBAGG-CMPLNLGQSA-N
View compound in article | Full details | Search for this compound
Compound 56
Molecular Weight:324.3737
Molecular Formula:C19H20N2O3
InChIKey:YQGJNCROJYEFIH-YQVWRLOYSA-N
View compound in article | Full details | Search for this compound
Compound 58
Molecular Weight:201.2197
Molecular Formula:C9H15NO4
InChIKey:UFCPAWUKDLQLFS-COBSHVIPSA-N
View compound in article | Full details | Search for this compound
Compound 57
Molecular Weight:200.2316
Molecular Formula:C10H16O4
InChIKey:GZVXALXOWVXZLH-GJIOHYHPSA-N
View compound in article | Full details | Search for this compound
Compound 58a
Molecular Weight:201.2197
Molecular Formula:C9H15NO4
InChIKey:UFCPAWUKDLQLFS-RNFRBKRXSA-N
View compound in article | Full details | Search for this compound
Compound 58b
Molecular Weight:201.2197
Molecular Formula:C9H15NO4
InChIKey:UFCPAWUKDLQLFS-NKWVEPMBSA-N
View compound in article | Full details | Search for this compound
Compound 57a
Molecular Weight:200.2316
Molecular Formula:C10H16O4
InChIKey:GZVXALXOWVXZLH-GJIOHYHPSA-N
View compound in article | Full details | Search for this compound
Compound 57b
Molecular Weight:200.2316
Molecular Formula:C10H16O4
InChIKey:GZVXALXOWVXZLH-SLGIHZDVSA-N
View compound in article | Full details | Search for this compound
Compound 59
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 61
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 62
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 63
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 65
Molecular Weight:225.2806
Molecular Formula:C12H17NO3
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 66a
Molecular Weight:178.206
Molecular Formula:C10H11NO2
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 64b
Molecular Weight:177.2179
Molecular Formula:C11H12O2
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 66b
Molecular Weight:178.206
Molecular Formula:C10H11NO2
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 67a
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:QRGSTISKDZCDHV-KMKOMSMNSA-N
View compound in article | Full details | Search for this compound
Compound 69
Molecular Weight:205.253
Molecular Formula:C12H15NO2
InChIKey:PBGOPDVEJUQQKF-VHSXEESVSA-N
View compound in article | Full details | Search for this compound
Compound 67b
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:QRGSTISKDZCDHV-XCVCLJGOSA-N
View compound in article | Full details | Search for this compound
Compound 70
Molecular Weight:129.157
Molecular Formula:C6H11NO2
InChIKey:UIVNUVZVHBKCOK-RFZPGFLSSA-N
View compound in article | Full details | Search for this compound
Compound 72
Molecular Weight:291.3422
Molecular Formula:C16H21NO4
InChIKey:YHNTYHCDGVGPMX-KWCYVHTRSA-N
View compound in article | Full details | Search for this compound
Compound 73
Molecular Weight:291.3422
Molecular Formula:C16H21NO4
InChIKey:YHNTYHCDGVGPMX-FPMFFAJLSA-N
View compound in article | Full details | Search for this compound
Compound 74
Molecular Weight:226.2689
Molecular Formula:C12H18O4
InChIKey:DWSRQJRGJUHSIM-MUNZNRDXSA-N
View compound in article | Full details | Search for this compound
Compound 75
Molecular Weight:317.3795
Molecular Formula:C18H23NO4
InChIKey:NHDIYKJXAVCJOX-ILXRZTDVSA-N
View compound in article | Full details | Search for this compound
Compound E-71
Molecular Weight:214.2582
Molecular Formula:C11H18O4
InChIKey:GYGMOLHWGMLEGA-ORZBULNSSA-N
View compound in article | Full details | Search for this compound
Compound Z-71
Molecular Weight:214.2582
Molecular Formula:C11H18O4
InChIKey:GYGMOLHWGMLEGA-XZLDQRQTSA-N
View compound in article | Full details | Search for this compound
Compound 77
Molecular Weight:613.6777
Molecular Formula:C38H36AlNO5
InChIKey:SNEKIHIXZNWXSY-QLBXQKMFSA-N
View compound in article | Full details | Search for this compound
Compound 76
Molecular Weight:155.1513
Molecular Formula:C7H9NO3
InChIKey:PNPVETUIPHVXGI-NSCUHMNNSA-N
View compound in article | Full details | Search for this compound
Compound 78
Molecular Weight:191.2264
Molecular Formula:C11H13NO2
InChIKey:QNEJEOULQGPSBD-VIFPVBQESA-N
View compound in article | Full details | Search for this compound
Compound 79
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 91
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 80
Molecular Weight:356.4171
Molecular Formula:C23H20N2O2
InChIKey:QFXUVUBVPPOPQZ-ZRNYENFQSA-N
View compound in article | Full details | Search for this compound
Compound 81
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 82
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 83
Molecular Weight:579.623
Molecular Formula:C23H20Cl2MgN2O10
InChIKey:PEJLVFVCRAZOOK-SIHOSDBDSA-L
View compound in article | Full details | Search for this compound
Compound 84
Molecular Weight:627.91
Molecular Formula:C17H24F6N2O8S2Zn
InChIKey:OIOOKPWYRJIXET-BEOOHURISA-L
View compound in article | Full details | Search for this compound
Compound 85
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 86
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 87
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 88
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 89
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 90
Molecular Weight:187.216
Molecular Formula:C7H9NO3S
InChIKey:XMJJPCJUQLGGND-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 93
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 92
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 94
Molecular Weight:200.2332
Molecular Formula:C13H12O2
InChIKey:WREMWLMAIUZCEE-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 96
Molecular Weight:247.2897
Molecular Formula:C14H17NO3
InChIKey:XIKVDBHOGKJJOO-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 97
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 98
Molecular Weight:189.2105
Molecular Formula:C11H11NO2
InChIKey:LCVUUGPCEKZAPG-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 99
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 102
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 103
Molecular Weight:241.307
Molecular Formula:C11H15NO3S
InChIKey:HAXGWOYUDAVHEM-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 104
Molecular Weight:244.289
Molecular Formula:C14H16N2O2
InChIKey:BWZQFUDKBBIFOH-GWCFXTLKSA-N
View compound in article | Full details | Search for this compound
Compound 105
Molecular Weight:611.7305
Molecular Formula:C35H41N5O5
InChIKey:PRTOWTFRORVLRA-SWWUGJJYSA-N
View compound in article | Full details | Search for this compound
Compound 106
Molecular Weight:367.4415
Molecular Formula:C21H25N3O3
InChIKey:QSSKIHWTOWUYEA-JXFKEZNVSA-N
View compound in article | Full details | Search for this compound
Compound 107
Molecular Weight:241.2405
Molecular Formula:C11H15NO5
InChIKey:HSUCSQQGPVSBLR-RTMURIBGSA-N
View compound in article | Full details | Search for this compound
Compound 108
Molecular Weight:364.393
Molecular Formula:C18H24N2O6
InChIKey:FKDAMDPEVWGZND-HUUCEWRRSA-N
View compound in article | Full details | Search for this compound
Compound 109
Molecular Weight:364.393
Molecular Formula:C18H24N2O6
InChIKey:FKDAMDPEVWGZND-LSDHHAIUSA-N
View compound in article | Full details | Search for this compound
Compound E-107
Molecular Weight:241.2405
Molecular Formula:C11H15NO5
InChIKey:HSUCSQQGPVSBLR-RTMURIBGSA-N
View compound in article | Full details | Search for this compound
Compound Z-107
Molecular Weight:241.2405
Molecular Formula:C11H15NO5
InChIKey:HSUCSQQGPVSBLR-VEMNSZJBSA-N
View compound in article | Full details | Search for this compound
Compound 110
Molecular Weight:323.3856
Molecular Formula:C20H21NO3
InChIKey:RJEFSJBIUXLNAD-VSRBDQBUSA-N
View compound in article | Full details | Search for this compound
Compound 111
Molecular Weight:446.5381
Molecular Formula:C27H30N2O4
InChIKey:SSDYSLIJQAVADK-KEKNWZKVSA-N
View compound in article | Full details | Search for this compound
Compound 113a
Molecular Weight:381.4681
Molecular Formula:C22H27N3O3
InChIKey:CLWBHKYIRLSJBD-CSODHUTKSA-N
View compound in article | Full details | Search for this compound
Compound 114a
Molecular Weight:381.4681
Molecular Formula:C22H27N3O3
InChIKey:CLWBHKYIRLSJBD-CBGDNZLLSA-N
View compound in article | Full details | Search for this compound
Compound 113b
Molecular Weight:409.5212
Molecular Formula:C24H31N3O3
InChIKey:JDCWJDSZBTYJIV-RZFNWQHOSA-N
View compound in article | Full details | Search for this compound
Compound 114b
Molecular Weight:409.5212
Molecular Formula:C24H31N3O3
InChIKey:JDCWJDSZBTYJIV-JMUQELJHSA-N
View compound in article | Full details | Search for this compound
Compound 114
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 113
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 115
Molecular Weight:273.2839
Molecular Formula:C15H15NO4
InChIKey:WLVOQWAJJPFVPX-SMDDNHRTSA-N
View compound in article | Full details | Search for this compound
Compound 116
Molecular Weight:396.4364
Molecular Formula:C22H24N2O5
InChIKey:ORTYGYGDUZGGQN-RCLSDMTESA-N
View compound in article | Full details | Search for this compound
Compound 117
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 118
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:BWHOZHOGCMHOBV-BQYQJAHWSA-N
View compound in article | Full details | Search for this compound
Compound 119
Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:JSCPGPKWAGKQKA-CDKJVOIVSA-N
View compound in article | Full details | Search for this compound
Compound 120
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 122
Molecular Weight:724.149
Molecular Formula:C25H28CuF6N2O8S2
InChIKey:UZBQKBHWYJOGAJ-KEHAGZLWSA-L
View compound in article | Full details | Search for this compound
Compound 121
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 120a
Molecular Weight:220.2213
Molecular Formula:C12H12O4
InChIKey:HPLVTKYRGZZXJF-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 120b
Molecular Weight:248.2744
Molecular Formula:C14H16O4
InChIKey:VUWPIBNKJSEYIN-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 120c
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:FMBOQULYOCJTME-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 120d
Molecular Weight:214.2582
Molecular Formula:C11H18O4
InChIKey:KHLQZLQKIPCFJF-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 121a
Molecular Weight:343.3737
Molecular Formula:C19H21NO5
InChIKey:MDPYZJHRTMSFSP-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 121b
Molecular Weight:371.4269
Molecular Formula:C21H25NO5
InChIKey:MNCKGDYZNZSBHJ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 121c
Molecular Weight:309.3575
Molecular Formula:C16H23NO5
InChIKey:UNZUVRUNQQZCDK-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 121d
Molecular Weight:337.4107
Molecular Formula:C18H27NO5
InChIKey:XBXSYEIDXBCIGE-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 123
Molecular Weight:164.2044
Molecular Formula:C9H12N2O
InChIKey:RKFPPQJJCPXERZ-SNAWJCMRSA-N
View compound in article | Full details | Search for this compound
Compound 124
Molecular Weight:287.3568
Molecular Formula:C16H21N3O2
InChIKey:WPABANSBCZHROA-CYBMUJFWSA-N
View compound in article | Full details | Search for this compound
Compound 126
Molecular Weight:420.372
Molecular Formula:C18H14F6N2OS
InChIKey:SUSUBFXIXQAEHC-LSDHHAIUSA-N
View compound in article | Full details | Search for this compound
Compound 125
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 127
Molecular Weight:962.653
Molecular Formula:C60H36Li3O6Y
InChIKey:SYAJWALQLAUGBC-UHFFFAOYSA-H
View compound in article | Full details | Search for this compound
Compound 128
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 129
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 130
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 131
Molecular Weight:261.3163
Molecular Formula:C15H19NO3
InChIKey:ZXHXVWQMNAYKDY-NQPRBDNZSA-N
View compound in article | Full details | Search for this compound
Compound 132
Molecular Weight:261.3163
Molecular Formula:C15H19NO3
InChIKey:XLAORTOETVRAAG-AMVTZNPPSA-N
View compound in article | Full details | Search for this compound
Compound 133
Molecular Weight:245.2738
Molecular Formula:C14H15NO3
InChIKey:DJZFGBTVCPIEDS-XFFZJAGNSA-N
View compound in article | Full details | Search for this compound
Compound 134
Molecular Weight:245.2738
Molecular Formula:C14H15NO3
InChIKey:LKIFTQSUCUITOY-VMPITWQZSA-N
View compound in article | Full details | Search for this compound
Compound 31a
Molecular Weight:157.1671
Molecular Formula:C7H11NO3
InChIKey:YTHHIYNAYAXMKI-FPLPWBNLSA-N
View compound in article | Full details | Search for this compound
Compound 135
Molecular Weight:223.2683
Molecular Formula:C12H17NO3
InChIKey:MZNBNPWFHGWAGH-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 136
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 137
Molecular Weight:179.2157
Molecular Formula:C10H13NO2
InChIKey:HMXIQGDRQJPMQI-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 138
Molecular Weight:244.289
Molecular Formula:C14H16N2O2
InChIKey:BWZQFUDKBBIFOH-GWCFXTLKSA-N
View compound in article | Full details | Search for this compound
Compound 139
Molecular Weight:481.5408
Molecular Formula:C26H31N3O6
InChIKey:FIZMEINSEKGTRT-AVRDEDQJSA-N
View compound in article | Full details | Search for this compound
Compound 140
Molecular Weight:218.2502
Molecular Formula:C9H18N2O4
InChIKey:ZHTIXJUOUJKRRR-LURJTMIESA-N
View compound in article | Full details | Search for this compound
Compound 146
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 144
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 147
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 148
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 149
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 147a
Molecular Weight:395.4914
Molecular Formula:C24H29NO4
InChIKey:ORXXUDLYHNUEJB-IBGZPJMESA-N
View compound in article | Full details | Search for this compound
Compound 147b
Molecular Weight:471.5873
Molecular Formula:C30H33NO4
InChIKey:IBQQRLASYJCWBW-MHZLTWQESA-N
View compound in article | Full details | Search for this compound
Compound 147c
Molecular Weight:437.5711
Molecular Formula:C27H35NO4
InChIKey:IIFPINORVUWMGT-UIDYPRJRSA-N
View compound in article | Full details | Search for this compound
Compound 148a
Molecular Weight:500.7024
Molecular Formula:C27H40N2O5Si
InChIKey:GBCXVQSRBOAAGF-OFVILXPXSA-N
View compound in article | Full details | Search for this compound
Compound 148b
Molecular Weight:576.7984
Molecular Formula:C33H44N2O5Si
InChIKey:SDNZJHKZVXJSAK-SMCANUKXSA-N
View compound in article | Full details | Search for this compound
Compound 148c
Molecular Weight:542.7821
Molecular Formula:C30H46N2O5Si
InChIKey:KZWSRGYBSOLCEP-ISJPVSPGSA-N
View compound in article | Full details | Search for this compound
Compound 149a
Molecular Weight:500.7024
Molecular Formula:C27H40N2O5Si
InChIKey:GBCXVQSRBOAAGF-SQJMNOBHSA-N
View compound in article | Full details | Search for this compound
Compound 149b
Molecular Weight:576.7984
Molecular Formula:C33H44N2O5Si
InChIKey:SDNZJHKZVXJSAK-IGYGKHONSA-N
View compound in article | Full details | Search for this compound
Compound 149c
Molecular Weight:542.7821
Molecular Formula:C30H46N2O5Si
InChIKey:KZWSRGYBSOLCEP-HMCKCBAOSA-N
View compound in article | Full details | Search for this compound
Compound 150
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 152
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 151
Molecular Weight:362.4647
Molecular Formula:C23H26N2O2
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 150a
Molecular Weight:200.2316
Molecular Formula:C10H16O4
InChIKey:VMKTWDDHIHCHFX-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 150b
Molecular Weight:242.3114
Molecular Formula:C13H22O4
InChIKey:ODHIUCXWGBUWRF-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 150c
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:GWXKCEDJZQBQQY-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 150d
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:FMBOQULYOCJTME-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 152a
Molecular Weight:305.4427
Molecular Formula:C13H27NO5Si
InChIKey:KZHRVRGIKYVUSE-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 152b
Molecular Weight:347.5224
Molecular Formula:C16H33NO5Si
InChIKey:BXAPZLDUKURHEX-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 152c
Molecular Weight:291.4161
Molecular Formula:C12H25NO5Si
InChIKey:MEXFKYWGKJIGCN-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 152d
Molecular Weight:291.4161
Molecular Formula:C12H25NO5Si
InChIKey:RIUHYTXSTRLVCN-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 153
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 154
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 155
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 156
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 157
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 158
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 161
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 159
Molecular Weight:166.1341
Molecular Formula:C7H6N2O3
InChIKey:GQMMRLBWXCGBEV-VMPITWQZSA-N
View compound in article | Full details | Search for this compound
Compound 160
Molecular Weight:293.2753
Molecular Formula:C13H15N3O5
InChIKey:FZYXNZPZHKCSOE-NTEUORMPSA-N
View compound in article | Full details | Search for this compound
Compound 188
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 186
Molecular Weight:98.0999
Molecular Formula:C5H6O2
InChIKey:FMVJYQGSRWVMQV-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 162
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 163
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 164
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 165
Molecular Weight:1159.583
Molecular Formula:C72H104Al2N4O5
InChIKey:DZERYWRJARUEFN-UGIKXLIJSA-J
View compound in article | Full details | Search for this compound
Compound 166
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 167
Molecular Weight:277.3157
Molecular Formula:C15H19NO4
InChIKey:SDTIFKUSKQBDMA-GCZGVDRJSA-N
View compound in article | Full details | Search for this compound
Compound 168
Molecular Weight:295.3309
Molecular Formula:C15H21NO5
InChIKey:OGLMXMJTACJCOO-YPMHNXCESA-N
View compound in article | Full details | Search for this compound
Compound 169
Molecular Weight:295.3309
Molecular Formula:C15H21NO5
InChIKey:OGLMXMJTACJCOO-DGCLKSJQSA-N
View compound in article | Full details | Search for this compound
Compound 170
Molecular Weight:597.5119
Molecular Formula:C24H23F12NOSi
InChIKey:MOHRGTBNEJKFMB-IBGZPJMESA-N
View compound in article | Full details | Search for this compound
Compound 171
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 172
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 173
Molecular Weight:828.0046
Molecular Formula:C46H61N5O9
InChIKey:SGYWRYSBQPUOIK-MZOYTQLQSA-N
View compound in article | Full details | Search for this compound
Compound 174
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 174a
Molecular Weight:321.4113
Molecular Formula:C18H27NO4
InChIKey:MKZLCZPBEZEAPZ-HNMKQIAWSA-N
View compound in article | Full details | Search for this compound
Compound 174b
Molecular Weight:335.4379
Molecular Formula:C19H29NO4
InChIKey:PXCKIYNMGNDTIS-SQVRNEIYSA-N
View compound in article | Full details | Search for this compound
Compound 174c
Molecular Weight:265.305
Molecular Formula:C14H19NO4
InChIKey:LLMDPCFQYUZVED-BTAWCLGRSA-N
View compound in article | Full details | Search for this compound
Compound 174d
Molecular Weight:279.3315
Molecular Formula:C15H21NO4
InChIKey:WBWDJBQFBOAPPU-HPUUJOOBSA-N
View compound in article | Full details | Search for this compound
Compound 175
Molecular Weight:117.1033
Molecular Formula:C4H7NO3
InChIKey:MWOBRJZWNNCTSK-HWKANZROSA-N
View compound in article | Full details | Search for this compound
Compound 176
Molecular Weight:594.614
Molecular Formula:C29H28F6N4OS
InChIKey:IQMKPBFOEWWDIQ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 178
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 177
Molecular Weight:357.3402
Molecular Formula:C19H20NO4P
InChIKey:DMKOEAUNIVCIPW-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 179
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 180
Molecular Weight:184.2355
Molecular Formula:C9H16N2O2
InChIKey:ITHSXKQIEXYJGK-YRNVUSSQSA-N
View compound in article | Full details | Search for this compound
Compound 181
Molecular Weight:352.448
Molecular Formula:C17H24N2O4S
InChIKey:HGEKKKHFHMLBQZ-PBHICJAKSA-N
View compound in article | Full details | Search for this compound
Compound 182
Molecular Weight:216.2789
Molecular Formula:C13H16N2O
InChIKey:BQLANWFNFWQPCH-KYPMKJFLSA-N
View compound in article | Full details | Search for this compound
Compound 183
Molecular Weight:231.2936
Molecular Formula:C13H17N3O
InChIKey:IRSSMUJWUQUTMI-RQOWECAXSA-N
View compound in article | Full details | Search for this compound
Compound 184
Molecular Weight:474.5449
Molecular Formula:C29H30O6
InChIKey:WIFQAEKDWPKCAQ-MVOVIXLKSA-N
View compound in article | Full details | Search for this compound
Compound 185
Molecular Weight:489.5595
Molecular Formula:C29H31NO6
InChIKey:ZLAKCYVPLRTDOG-PMBHKHONSA-N
View compound in article | Full details | Search for this compound
Compound 187
Molecular Weight:223.2252
Molecular Formula:C11H13NO4
InChIKey:PGGQCHVPWSXPSI-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 190
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 191
Molecular Weight:141.1247
Molecular Formula:C6H7NO3
InChIKey:HIBSYUPTCGGRSD-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 192
Molecular Weight:262.2613
Molecular Formula:C13H14N2O4
InChIKey:IGROFXIRQDIPAL-UVTDQMKNSA-N
View compound in article | Full details | Search for this compound
Compound 193
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 194
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 195
Molecular Weight:413.582
Molecular Formula:C23H31NO4Si
InChIKey:WPHODUZPFSNCFS-MTLCJGDQSA-N
View compound in article | Full details | Search for this compound
Compound 196
Molecular Weight:531.736
Molecular Formula:C27H37NO6SSi
InChIKey:TWPGCBYHTIXACD-OJVSJSBUSA-N
View compound in article | Full details | Search for this compound
Compound 197
Molecular Weight:531.736
Molecular Formula:C27H37NO6SSi
InChIKey:TWPGCBYHTIXACD-OJVSJSBUSA-N
View compound in article | Full details | Search for this compound
Compound 198
Molecular Weight:195.2582
Molecular Formula:C11H17NO2
InChIKey:KDJCHLBDOONQFO-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 199
Molecular Weight:195.2582
Molecular Formula:C11H17NO2
InChIKey:UVFZGHKGEDZCJK-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 200
Molecular Weight:334.41
Molecular Formula:C16H14O4S2
InChIKey:MZRCSZMGBMHTJW-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 202
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 203
Molecular Weight:458.5073
Molecular Formula:C30H22N2O3
InChIKey:YNAUPJHAAOZVLV-UIOOFZCWSA-N
View compound in article | Full details | Search for this compound
Compound 204
Molecular Weight:230.2625
Molecular Formula:C13H14N2O2
InChIKey:MYNUGBXKVDPZEK-QHHAFSJGSA-N
View compound in article | Full details | Search for this compound
Compound 205
Molecular Weight:137.136
Molecular Formula:C7H7NO2
InChIKey:VDEUYMSGMPQMIK-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 206
Molecular Weight:207.2258
Molecular Formula:C11H13NO3
InChIKey:HYDBMESHMNVRRA-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 207
Molecular Weight:207.2258
Molecular Formula:C11H13NO3
InChIKey:WGSNLKSKYSECJM-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 208
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound

VIEW

  1. 1 - 250