Standard Article

Organocatalysis

Part 1. Homogeneous Catalysis

  1. Isabelle McCort-Tranchepain,
  2. Morgane Petit,
  3. Peter I. Dalko

Published Online: 15 JUL 2010

DOI: 10.1002/9783527628698.hgc009

Handbook of Green Chemistry

Handbook of Green Chemistry

How to Cite

McCort-Tranchepain, I., Petit, M. and Dalko, P. I. 2010. Organocatalysis. Handbook of Green Chemistry. 1:9:255–318.

Author Information

  1. Université Paris Descartes, Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, Paris, France

Publication History

  1. Published Online: 15 JUL 2010

Chemistry Terms

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Abstract

Asymmetric organocatalytic reactions are continuing to provide more and more efficient and environmentally friendly synthetic alternatives to metal complex-mediated reactions. Although substrate dependence remains an important issue, there are increasing numbers of transformations that have reached the standards of current asymmetric reactions.

Keywords:

  • asymmetric synthesis;
  • organocatalysis;
  • nucleophilic addition;
  • alkene addition;
  • green chemistry

Featured Compounds

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  1. 1 - 100
Compound 28
Molecular Weight:358.5402
Molecular Formula:C24H39P
InChIKey:LTXIQCIVTVZGOA-CAMXOCNWSA-N
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Compound 17
Molecular Weight:842.9451
Molecular Formula:C51H52N6O2P2
InChIKey:HTIRTTKKZTYOST-UHFFFAOYSA-N
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Compound 42
Molecular Weight:394.4635
Molecular Formula:C23H26N2O4
InChIKey:RSHYJKVRZCEMSO-FKBYEOEOSA-N
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Compound 10a
Molecular Weight:466.5675
Molecular Formula:C31H30O4
InChIKey:OWVIRVJQDVCGQX-NSOVKSMOSA-N
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Compound 75
Molecular Weight:367.872
Molecular Formula:C21H22ClN3O
InChIKey:GUECWMLEUCWYOS-OZYANKIXSA-M
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Compound 60
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 48.HX
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 31
Molecular Weight:853.0139
Molecular Formula:C54H52N4O6
InChIKey:RMHFANAFTWZAKJ-JAXLAYQKSA-N
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Compound 33
Molecular Weight:392.36
Molecular Formula:C14H18F6N2O2S
InChIKey:ZNAMJUPIFGLJDN-RKDXNWHRSA-N
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Compound 5.p-TSA
Molecular Weight:418.55
Molecular Formula:C22H30N2O4S
InChIKey:DZHBZDHXBIPFLH-KYSPHBLOSA-N
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Compound 30
Molecular Weight:376.4929
Molecular Formula:C27H24N2
InChIKey:CYPLHBQOKKNBSN-NHCUHLMSSA-N
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Compound 48a
Molecular Weight:218.2948
Molecular Formula:C13H18N2O
InChIKey:UACYWOJLWBDSHG-NSHDSACASA-N
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Compound 3a
Molecular Weight:325.52
Molecular Formula:C20H27NOSi
InChIKey:Not Available
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Compound (R)-3a
Molecular Weight:325.52
Molecular Formula:C20H27NOSi
InChIKey:Not Available
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Compound 45
Molecular Weight:390.586
Molecular Formula:C21H34N4OS
InChIKey:CNEVMNSDRMDKFO-KZNAEPCWSA-N
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Compound 3c
Molecular Weight:1161.621
Molecular Formula:C36H25F34NOSi
InChIKey:UPOGXAQYHYZJRF-IBGZPJMESA-N
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Compound 27
Molecular Weight:660.626
Molecular Formula:C45H36FeN2
InChIKey:NRVHUMOOLXYRGT-UHFFFAOYSA-N
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Compound 18
Molecular Weight:498.582
Molecular Formula:C23H44N6O2P2
InChIKey:GKCOBJYSFNJADZ-SSGKUCQKSA-N
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Compound 5.TFA
Molecular Weight:360.3713
Molecular Formula:C17H23F3N2O3
InChIKey:PSURRFOPVPJWSP-KYSPHBLOSA-N
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Compound C-2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 71
Molecular Weight:442.5494
Molecular Formula:C28H30N2O3
InChIKey:JLFFUQBWAOTOPB-LSQWXYBESA-N
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Compound 59
Molecular Weight:258.2677
Molecular Formula:C12H18O6
InChIKey:IVWWFWFVSWOTLP-RWYTXXIDSA-N
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Compound 38
Molecular Weight:574.818
Molecular Formula:C31H50N4O4S
InChIKey:BOFCLIFENISFHX-SINPPJPYSA-N
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Compound I
Molecular Weight:253.2943
Molecular Formula:C13H19NO4
InChIKey:LJXTYJXBORAIHX-UHFFFAOYSA-N
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Compound 5.TfOH
Molecular Weight:396.425
Molecular Formula:C16H23F3N2O4S
InChIKey:IUSGJGFQORLYCC-KYSPHBLOSA-N
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Compound 29
Molecular Weight:1437.8061
Molecular Formula:C79H112N12O13
InChIKey:XFRUMLNXBBWBMT-BSOYYHKASA-P
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Compound 50
Molecular Weight:160.2572
Molecular Formula:C8H20N2O
InChIKey:XRQLDNYYTJQSHA-QRPNPIFTSA-M
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Compound 61
Molecular Weight:396.3915
Molecular Formula:C25H16O5
InChIKey:CVEUEGQSDBSNMJ-UHFFFAOYSA-N
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Compound 55
Molecular Weight:264.426
Molecular Formula:C16H24OS
InChIKey:RAUKEFYWSAFZAX-VJPYIOSNSA-N
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Compound 69
Molecular Weight:742.6456
Molecular Formula:C42H32O9P2
InChIKey:SASLKKCTLQWVGI-UHFFFAOYSA-N
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Compound 51
Molecular Weight:139.1585
Molecular Formula:C5H9N5
InChIKey:XUHYQIQIENDJER-BYPYZUCNSA-N
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Compound 10c
Molecular Weight:666.8022
Molecular Formula:C47H38O4
InChIKey:WTZVNZRNIOJACO-CXNSMIOJSA-N
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Compound 63
Molecular Weight:532.6291
Molecular Formula:C27H40N4O7
InChIKey:PPMVQCXBLRLORE-IWLVTHKOSA-N
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Compound 43
Molecular Weight:262.3474
Molecular Formula:C15H22N2O2
InChIKey:WWUZCRRIJZUXEZ-AWEZNQCLSA-N
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Compound 47
Molecular Weight:413.424
Molecular Formula:C17H21F6N3S
InChIKey:NQRCAVZHOLYEBJ-ZIAGYGMSSA-N
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 5.HX
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 46
Molecular Weight:425.588
Molecular Formula:C27H27N3S
InChIKey:GGAOZHGXEGTTFN-PBXQCXKZSA-N
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Compound 22
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 68
Molecular Weight:426.169
Molecular Formula:C20H11Ar2O4P
InChIKey:WLUJYHRDUNUBOW-UHFFFAOYSA-N
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Compound 3b
Molecular Weight:597.5119
Molecular Formula:C24H23F12NOSi
InChIKey:MOHRGTBNEJKFMB-IBGZPJMESA-N
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Compound 6
Molecular Weight:324.4168
Molecular Formula:C20H24N2O2
InChIKey:LOUPRKONTZGTKE-HAOVMRFASA-N
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Compound 8
Molecular Weight:324.4168
Molecular Formula:C20H24N2O2
InChIKey:LOUPRKONTZGTKE-MYUJHIMRSA-N
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Compound 23
Molecular Weight:384.623
Molecular Formula:C20H40N4OS
InChIKey:HJYZGDLQPZQFIN-BRWVUGGUSA-N
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Compound 44
Molecular Weight:182.3058
Molecular Formula:C11H22N2
InChIKey:LTQBUTVRZPYPEU-GHMZBOCLSA-N
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Compound 65.HCLO4
Molecular Weight:370.785
Molecular Formula:C16H19ClN2O6
InChIKey:OCAUSDAAAILUSM-SLHAJLBXSA-N
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Compound 15
Molecular Weight:446.5812
Molecular Formula:C28H34N2O3
InChIKey:ZNAQJQQYNJCUMP-YNJKOYDBSA-N
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Compound 48
Molecular Weight:Not Available
Molecular Formula:(CH2)nC14H18N2O
InChIKey:OEGYNDQXDKPJCH-ZDUSSCGKSA-N
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Compound 48b
Molecular Weight:244.3321
Molecular Formula:C15H20N2O
InChIKey:OEGYNDQXDKPJCH-ZDUSSCGKSA-N
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Compound 2b
Molecular Weight:525.3307
Molecular Formula:C21H15F12NO
InChIKey:ITXPGQOGEYWAKW-INIZCTEOSA-N
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Compound 35a
Molecular Weight:590.4756
Molecular Formula:C32H19N2O8P
InChIKey:ZAVIDRFWCFHRJK-UHFFFAOYSA-N
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Compound 65
Molecular Weight:270.3263
Molecular Formula:C16H18N2O2
InChIKey:IQIMPHPFMHVWBZ-ZFWWWQNUSA-N
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Compound 74
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 72
Molecular Weight:270.2488
Molecular Formula:C10H17F3N2O3
InChIKey:HKHKOEMMPVPVOS-OGFXRTJISA-N
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Compound Rotamer A
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 34
Molecular Weight:650.914
Molecular Formula:C37H54N4O4S
InChIKey:HLBWYDYPUBVZMP-OCXGOZKISA-N
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Compound 56
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 5.HCl
Molecular Weight:282.809
Molecular Formula:C15H23ClN2O
InChIKey:TWORUGGOMHQXAW-KYSPHBLOSA-N
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Compound 5
Molecular Weight:246.348
Molecular Formula:C15H22N2O
InChIKey:SKHPYKHVYFTIOI-JSGCOSHPSA-N
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Compound 21
Molecular Weight:594.7596
Molecular Formula:C41H39FN2O
InChIKey:CRTWLJYQHHCQID-PTEQEHSKSA-M
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Compound 67
Molecular Weight:293.4458
Molecular Formula:C21H27N
InChIKey:PHKHWUVAUXBNPC-FQEVSTJZSA-N
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Compound C-1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 48c
Molecular Weight:258.3587
Molecular Formula:C16H22N2O
InChIKey:LQRYNHHESCAKMH-AWEZNQCLSA-N
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Compound 4
Molecular Weight:267.3654
Molecular Formula:C18H21NO
InChIKey:CGUGCZSRPDCLBT-KRWDZBQOSA-N
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Compound 4a
Molecular Weight:267.3654
Molecular Formula:C18H21NO
InChIKey:CGUGCZSRPDCLBT-KRWDZBQOSA-N
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Compound 2a
Molecular Weight:253.3389
Molecular Formula:C17H19NO
InChIKey:OGCGXUGBDJGFFY-INIZCTEOSA-N
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Compound 25
Molecular Weight:583.59
Molecular Formula:C31H23F6N3S
InChIKey:Not Available
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Compound 52
Molecular Weight:220.2676
Molecular Formula:C12H16N2O2
InChIKey:YAYFGCSJMYVTMF-VUWPPUDQSA-N
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Compound 73
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 70.2HCl
Molecular Weight:241.201
Molecular Formula:C10H22Cl2N2
InChIKey:UIAHGDBWKRHPAY-XRIOVQLTSA-N
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Compound 66
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 54
Molecular Weight:282.337
Molecular Formula:C17H18N2O2
InChIKey:HPCWKBVSJGWXMC-KSCSMHSMSA-N
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Compound 44.pTSA
Molecular Weight:354.507
Molecular Formula:C18H30N2O3S
InChIKey:DPAWFNOFVXYIKY-NDXYWBNTSA-N
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Compound 16
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 40
Molecular Weight:1280.0276
Molecular Formula:C72H46F12IN
InChIKey:SEUPHUIZSCWPRA-UHFFFAOYSA-M
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Compound 41
Molecular Weight:454.671
Molecular Formula:C26H38N4OS
InChIKey:TYYBWOMDGCWLGF-MZYLBHOOSA-N
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Compound 19
Molecular Weight:414.4962
Molecular Formula:C26H26N2O3
InChIKey:MKLYYDRSHXDKNA-UJXVZYGKSA-N
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Compound 20
Molecular Weight:414.4962
Molecular Formula:C26H26N2O3
InChIKey:MKLYYDRSHXDKNA-VRCHSZTHSA-N
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Compound 32
Molecular Weight:500.6301
Molecular Formula:C34H32N2O2
InChIKey:IFIRZHVEJFSVKE-SAUGTVQKSA-N
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Compound 36
Molecular Weight:398.563
Molecular Formula:C19H34N4O3S
InChIKey:CBZTULSJTZUBOY-BZUAXINKSA-N
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Compound C-3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 13
Molecular Weight:212.2902
Molecular Formula:C14H16N2
InChIKey:PONXTPCRRASWKW-ZIAGYGMSSA-N
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Compound 39
Molecular Weight:566.798
Molecular Formula:C32H46N4O3S
InChIKey:NVTLOXOBQAJWCW-IAFVRIFVSA-N
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Compound 1
Molecular Weight:115.1305
Molecular Formula:C5H9NO2
InChIKey:ONIBWKKTOPOVIA-BYPYZUCNSA-N
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Compound 57
Molecular Weight:163.1733
Molecular Formula:C9H9NO2
InChIKey:QNRXNRGSOJZINA-QMMMGPOBSA-N
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Compound 64
Molecular Weight:303.4854
Molecular Formula:C19H33N3
InChIKey:WLERMHUTKPCLNK-OALUTQOASA-N
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Compound 49
Molecular Weight:400.415
Molecular Formula:C18H19F3N2O3S
InChIKey:MBNCYOAVDQVATB-UQKRIMTDSA-N
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Compound 12
Molecular Weight:622.6724
Molecular Formula:C44H32P2
InChIKey:Not Available
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Compound 24
Molecular Weight:310.3902
Molecular Formula:C19H22N2O2
InChIKey:ULTQUFCPWDEOND-BAUCMMJXSA-N
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Compound 11
Molecular Weight:286.324
Molecular Formula:C20H14O2
InChIKey:PPTXVXKCQZKFBN-UHFFFAOYSA-N
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Compound 14
Molecular Weight:114.1888
Molecular Formula:C6H14N2
InChIKey:SSJXIUAHEKJCMH-PHDIDXHHSA-N
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Compound 62
Molecular Weight:302.2772
Molecular Formula:C13H18O8
InChIKey:DJTMIVAUVZAXBV-BREBYQMCSA-N
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Compound 7
Molecular Weight:294.3908
Molecular Formula:C19H22N2O
InChIKey:KMPWYEUPVWOPIM-BRNCMBGJSA-N
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Compound 9
Molecular Weight:294.3908
Molecular Formula:C19H22N2O
InChIKey:KMPWYEUPVWOPIM-LRQCXVISSA-N
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Compound 3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 37
Molecular Weight:451
Molecular Formula:C27H31ClN2O2
InChIKey:JYDIJFKNXHPWBJ-GOGFHWEMSA-M
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Compound 10b
Molecular Weight:706.8661
Molecular Formula:C50H42O4
InChIKey:CJCPHRPISJGNDL-MVRBIKRMSA-N
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Compound 26
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 53
Molecular Weight:244.2956
Molecular Formula:C12H16N6
InChIKey:NQHRDPMJNWQISK-NUHJPDEHSA-N
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Compound 35b
Molecular Weight:752.9589
Molecular Formula:C50H57O4P
InChIKey:AGQAQYPGJDBIQR-UHFFFAOYSA-N
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