Standard Article

Development and Application of Isocyanide-based Multicomponent Reactions

Part 7. Green Synthesis

  1. Jieping Zhu1,
  2. Qian Wang1,
  3. Mei-Xiang Wang2

Published Online: 15 APR 2012

DOI: 10.1002/9783527628698.hgc076

Handbook of Green Chemistry

Handbook of Green Chemistry

How to Cite

Zhu, J., Wang, Q. and Wang, M.-X. 2012. Development and Application of Isocyanide-based Multicomponent Reactions. Handbook of Green Chemistry. 7:5:121–157.

Author Information

  1. 1

    École Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, Lausanne, Switzerland

  2. 2

    Tsinghua University, The Key Laboratory of Bioorganic, Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Beijing, China

Publication History

  1. Published Online: 15 APR 2012

Chemistry Terms

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Abstract

Multicomponent reaction (MCR) is a process in which three or more reactants are combined in a single chemical operation to produce a compound that incorporates substantial portions of all starting materials. They are by definition sustainable chemistry and are inherently

  1. chemo- and regioselective, a prerequisite for a successful MCR since at least three reactive functional groups are involved and they react in an ordered and selective fashion;

  2. atom-economic since most of them involve addition rather than substitution reactions;

  3. step-efficient since they create at least two chemical bonds in one operation;

  4. convergent and efficient in generating molecular complexity and diversity;

  5. cost-effective since they reduce waste production significantly by minimizing the number of costly end-of-pipe treatments by decreasing the number of synthetic steps;

  6. operationally simple since most of the MCRs are performed under mild reaction conditions and in some cases even proceed spontaneously in the absence of an external reagent.

Using isocyanide-based MCRs as examples, the recent development and applications of this family of MCRs are illustrated in the context of green chemistry. Most of MCRs discussed in this chapter satisfy the following criteria:

  1. need no external reagent or, if required, in only a catalytic amount;

  2. produce minimum amounts of side products, in most cases water and low molecular weight alcohols;

  3. require no protective groups;

  4. create more than two chemical bonds.

Keywords:

  • green chemistry;
  • isocyanides;
  • multicomponent reactions;
  • Ugi reactions

Featured Compounds

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  1. 1 - 112
Compound 128
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound A
Molecular Weight:Not Available
Molecular Formula:Not Available
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Compound B
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound D
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound F
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound C
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound E
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 1
Molecular Weight:439.4611
Molecular Formula:C23H25N3O6
InChIKey:WFFGNVMOIDGOQC-LROBGIAVSA-N
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Compound 2
Molecular Weight:223.2252
Molecular Formula:C11H13NO4
InChIKey:NJSRYBIBUXBNSW-VIFPVBQESA-N
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Compound 4
Molecular Weight:157.276
Molecular Formula:C8H15NS
InChIKey:BQMNKSIPXWTEPI-ZETCQYMHSA-N
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Compound 5
Molecular Weight:316.459
Molecular Formula:C15H28N2O3S
InChIKey:MLQGICSXJVXJAU-KFJBMODSSA-N
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Compound 6
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:AVPYQKSLYISFPO-UHFFFAOYSA-N
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Compound 7
Molecular Weight:99.088
Molecular Formula:C4H5NO2
InChIKey:Not Available
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Compound 8
Molecular Weight:85.1475
Molecular Formula:C5H11N
InChIKey:Not Available
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Compound 9
Molecular Weight:306.787
Molecular Formula:C16H19ClN2O2
InChIKey:NHNKIXVWCPVFEE-DARJFKRNSA-N
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Compound 13
Molecular Weight:175.184
Molecular Formula:C10H9NO2
InChIKey:SKSIHYZCBHLEOB-UHFFFAOYSA-N
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Compound 15
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 16
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 17
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 21
Molecular Weight:676.9315
Molecular Formula:C39H60N6O4
InChIKey:GISFDDVCOZPDPQ-UHFFFAOYSA-N
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Compound 22
Molecular Weight:136.1943
Molecular Formula:C8H12N2
InChIKey:FDLQZKYLHJJBHD-UHFFFAOYSA-N
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Compound 23
Molecular Weight:348.3969
Molecular Formula:C17H24N4O4
InChIKey:LAOZPKBVLATEOF-UHFFFAOYSA-N
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Compound 31
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:Not Available
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Compound 24
Molecular Weight:96.0841
Molecular Formula:C5H4O2
InChIKey:HYBBIBNJHNGZAN-UHFFFAOYSA-N
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Compound 25
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:WGQKYBSKWIADBV-UHFFFAOYSA-N
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Compound 26
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:Not Available
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Compound 27
Molecular Weight:144.1253
Molecular Formula:C6H8O4
InChIKey:XLYMOEINVGRTEX-ONEGZZNKSA-N
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Compound 28
Molecular Weight:446.495
Molecular Formula:C26H26N2O5
InChIKey:JTANUYXDYRTBMY-XMLSHEPFSA-N
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Compound 30
Molecular Weight:247.2963
Molecular Formula:C12H17N5O
InChIKey:CXNOFXCYKBBQAR-UHFFFAOYSA-N
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Compound 32
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 33
Molecular Weight:569.7402
Molecular Formula:C33H43N7O2
InChIKey:QVZAZLNPEVADJL-UHFFFAOYSA-N
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Compound 36
Molecular Weight:517.6591
Molecular Formula:C31H39N3O4
InChIKey:YBQRPYXYPRWRHE-XMYOTZFWSA-N
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Compound 35
Molecular Weight:177.1998
Molecular Formula:C10H11NO2
InChIKey:TUQBDQPPBVABFN-VOTSOKGWSA-N
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Compound 37
Molecular Weight:517.6591
Molecular Formula:C31H39N3O4
InChIKey:VCPKLZQSYBGDNI-ISLYRVAYSA-N
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Compound 38
Molecular Weight:161.2004
Molecular Formula:C10H11NO
InChIKey:COEXIWUQQKISAJ-UHFFFAOYSA-N
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Compound 39
Molecular Weight:396.4794
Molecular Formula:C23H28N2O4
InChIKey:YKLVSVIKLXUPNT-UHFFFAOYSA-N
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Compound 40
Molecular Weight:515.6432
Molecular Formula:C31H37N3O4
InChIKey:FOEKEMAKULOAOK-UHFFFAOYSA-N
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Compound 36a
Molecular Weight:517.6591
Molecular Formula:C31H39N3O4
InChIKey:YBQRPYXYPRWRHE-LIUKAWEGSA-N
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Compound 36b
Molecular Weight:517.6591
Molecular Formula:C31H39N3O4
InChIKey:YBQRPYXYPRWRHE-YGDBUXKNSA-N
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Compound 41
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 42
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 46
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 47
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 48
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 53
Molecular Weight:154.1665
Molecular Formula:C7H10N2O2
InChIKey:FREGRQYTSPAJDX-WAYWQWQTSA-N
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Compound 54
Molecular Weight:403.4769
Molecular Formula:C23H25N5O2
InChIKey:CBQWJIAYZDBJBG-UHFFFAOYSA-N
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Compound 110
Molecular Weight:156.1806
Molecular Formula:C11H8O
InChIKey:SQAINHDHICKHLX-UHFFFAOYSA-N
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Compound 58
Molecular Weight:346.444
Molecular Formula:C18H22N2O3S
InChIKey:QPIHTPBWLAQVFO-UHFFFAOYSA-N
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Compound 66
Molecular Weight:360.6196
Molecular Formula:C24H44N2
InChIKey:KMUUPFCJNQIZCO-LYWYBQTLSA-N
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Compound 67
Molecular Weight:380.6092
Molecular Formula:C26H40N2
InChIKey:LIJBMRBBVAOQIH-MPCGXDHWSA-N
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Compound 68
Molecular Weight:885.3541
Molecular Formula:C56H92N4O4
InChIKey:SXMHOPCYMBPHRP-OGGBLFGJSA-N
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Compound 69
Molecular Weight:1306.9194
Molecular Formula:C78H135N3O12
InChIKey:LZACXZYQHXGBDP-UHFFFAOYSA-K
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Compound 70
Molecular Weight:176.2184
Molecular Formula:C9H12N4
InChIKey:DKFBZIIJBPFCKJ-UHFFFAOYSA-N
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Compound 71
Molecular Weight:972.1333
Molecular Formula:C51H69N7O12
InChIKey:ROTDMPZVUUVKBZ-UHFFFAOYSA-N
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Compound 72
Molecular Weight:247.2451
Molecular Formula:C10H17NO6
InChIKey:AQTUACKQXJNHFQ-LURJTMIESA-N
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Compound 73
Molecular Weight:150.173
Molecular Formula:C6H14O4
InChIKey:ZIBGPFATKBEMQZ-UHFFFAOYSA-N
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Compound 74
Molecular Weight:559.6496
Molecular Formula:C26H45N3O10
InChIKey:LQOSMVMIRROGTA-AOCRQIFASA-N
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Compound 76
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 77
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 78
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 79
Molecular Weight:267.3672
Molecular Formula:C14H25N3O2
InChIKey:SXUXLQNNCPIKBP-UHFFFAOYSA-N
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Compound 80
Molecular Weight:419.5145
Molecular Formula:C22H33N3O5
InChIKey:BWFSCIGCFMNHHQ-BQYQJAHWSA-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 86
Molecular Weight:139.1088
Molecular Formula:C6H5NO3
InChIKey:IQUPABOKLQSFBK-UHFFFAOYSA-N
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Compound 87
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 90
Molecular Weight:265.0053
Molecular Formula:C6H4INO3
InChIKey:BKQFOYCEUMVWOW-UHFFFAOYSA-N
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Compound 92
Molecular Weight:334.4546
Molecular Formula:C22H26N2O
InChIKey:HDTUIHJTHHKLNN-UHFFFAOYSA-N
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Compound 93
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 94
Molecular Weight:129.1586
Molecular Formula:C9H7N
InChIKey:AWJUIBRHMBBTKR-UHFFFAOYSA-N
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Compound 95
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 97
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 98
Molecular Weight:389.4007
Molecular Formula:C23H19NO5
InChIKey:IFHCSRDBSIGVFR-UHFFFAOYSA-N
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Compound 100
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 99
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 106
Molecular Weight:95.1026
Molecular Formula:C4H5N3
InChIKey:LJXQPZWIHJMPQQ-UHFFFAOYSA-N
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Compound 107
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 111
Molecular Weight:309.382
Molecular Formula:C18H15NO2S
InChIKey:XZBRMHJIFYNALR-CPNJWEJPSA-N
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Compound 112
Molecular Weight:407.459
Molecular Formula:C24H25NO5
InChIKey:VDNODOBSZOHFIE-UHFFFAOYSA-N
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Compound 113
Molecular Weight:560.661
Molecular Formula:C31H32N2O6S
InChIKey:WYMAOWHKKSBNAW-UHFFFAOYSA-N
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Compound 115
Molecular Weight:413.4205
Molecular Formula:C22H23NO7
InChIKey:HBAIIDIKPGLUOH-UHFFFAOYSA-N
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Compound 116
Molecular Weight:162.1421
Molecular Formula:C9H6O3
InChIKey:BQLSCAPEANVCOG-UHFFFAOYSA-N
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Compound 119
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 120
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 121
Molecular Weight:144.1253
Molecular Formula:C6H8O4
InChIKey:GXHFUVWIGNLZSC-UHFFFAOYSA-N
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Compound 122
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 127
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 126
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 129
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 130
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 131
Molecular Weight:224.3009
Molecular Formula:C15H16N2
InChIKey:YQTBSDQONCORLJ-UHFFFAOYSA-N
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Compound 132
Molecular Weight:169.2224
Molecular Formula:C12H11N
InChIKey:FAZLQQNVONHHCG-UHFFFAOYSA-N
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Compound 137
Molecular Weight:278.3914
Molecular Formula:C19H22N2
InChIKey:OFXVNATUYYFQLV-UHFFFAOYSA-N
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Compound 136
Molecular Weight:129.1586
Molecular Formula:C9H7N
InChIKey:CSZBAJSEZIGDHD-UHFFFAOYSA-N
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Compound 138
Molecular Weight:842.9451
Molecular Formula:C51H52N6O2P2
InChIKey:HTIRTTKKZTYOST-UHFFFAOYSA-N
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Compound 139
Molecular Weight:630.593
Molecular Formula:C37H42O6Ti
InChIKey:ASACUCBAGWQAFH-HVVJQNAGSA-N
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Compound 140
Molecular Weight:755.121
Molecular Formula:C27H21CuF6N3O8S2
InChIKey:IRYQYXQQBMSZEJ-LGUZPGMJSA-L
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Compound 141
Molecular Weight:607.245
Molecular Formula:C36H52AlClN2O2
InChIKey:KGVBCKDZFMLRMA-OHRASPNLSA-K
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Compound 142
Molecular Weight:586.8263
Molecular Formula:C37H55AlN2O2
InChIKey:DESAYIFUNLKGNY-OHRASPNLSA-L
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Compound 143
Molecular Weight:321.822
Molecular Formula:C16H16ClNO2S
InChIKey:GKTWGGQPFAXNFI-UHFFFAOYSA-N
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Compound 144
Molecular Weight:139.218
Molecular Formula:C7H9NS
InChIKey:OGUWOLDNYOTRBO-UHFFFAOYSA-N
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Compound 145
Molecular Weight:140.567
Molecular Formula:C7H5ClO
InChIKey:FPYUJUBAXZAQNL-UHFFFAOYSA-N
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Compound 146
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:DSPXASHHKFVPCL-UHFFFAOYSA-N
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Compound 147
Molecular Weight:307.795
Molecular Formula:C15H14ClNO2S
InChIKey:DCASRSISIKYPDD-UHFFFAOYSA-N
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Compound 148
Molecular Weight:761.837
Molecular Formula:C39H43N3O11S
InChIKey:PKVRCIRHQMSYJX-AIFWHQITSA-N
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Compound 149
Molecular Weight:297.3038
Molecular Formula:C14H19NO6
InChIKey:WUDBJPBNGJQAHL-NSHDSACASA-N
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Compound 150
Molecular Weight:541.376
Molecular Formula:C23H28INO6
InChIKey:YKHQBRCDOXZGQJ-KRWDZBQOSA-N
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Compound 151
Molecular Weight:133.1473
Molecular Formula:C8H7NO
InChIKey:MIEQKTRWKZYUPY-UHFFFAOYSA-N
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Compound 152
Molecular Weight:1031.902
Molecular Formula:C46H54IN3O14S
InChIKey:CEXMGPCQBDCFFL-BZLHUUGFSA-N
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  1. 1 - 112