Standard Article

Pericyclic Reactions in Water. Towards Green Chemistry

5. Reactions in Water

  1. Jaap E. Klijn,
  2. Jan B.F.N. Engberts

Published Online: 15 JUL 2010

DOI: 10.1002/9783527628698.hgc054

Handbook of Green Chemistry

Handbook of Green Chemistry

How to Cite

Klijn, J. E. and Engberts, J. B. 2010. Pericyclic Reactions in Water. Towards Green Chemistry. Handbook of Green Chemistry. 5:8:229–271.

Author Information

  1. University of Groningen, Stratingh Institute, Groningen, AG, The Netherlands

Publication History

  1. Published Online: 15 JUL 2010

Chemistry Terms

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Abstract

This chapter provides an overview of the recent progress in performing synthetically important pericyclic reactions in (and “on”) water. In the past, these reactions were almost exclusively carried out in organic solvents to avoid problems arising from the limited solubility of the reagents in aqueous media. In the early eighties of last century, however, it was found that, rather unexpectedly, many types of pericyclic transformations possess greatly enhanced rates and often more favorable stereochemistry in water. Detailed mechanistic studies have now revealed how these advantages of aqueous reaction media depend on the type of the reaction and on the structural features of the initial state (IS) and activated complex (AC) of the various cycloadditions. This work is reviewed in some detail. Enforced hydrophobic interactions of the IS as well as hydrogen-bond stabilization of the AC, characteristic for water as the reaction medium, were, in most cases, identified as major reasons for the observed kinetic and stereochemical phenomena. More recently it was found that there are also good possibilities for catalyzing pericyclic reactions in water. Particularly enantioselective Lewis acid-catalyzed Diels-Alder reactions have been investigated in detail. Green chemistry greatly benefits from these developments since water is the ultimate green solvent for enviromentally friendly chemical transformations. The future for aqueous organic chemistry looks bright.

Keywords:

  • pericyclic reactions;
  • water;
  • organic synthesis;
  • Diels–Alder reaction;
  • green chemistry;
  • hydrophobic interactions

Featured Compounds

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  1. 1 - 188
Compound 1
Molecular Weight:54.0904
Molecular Formula:C4H6
InChIKey:KAKZBPTYRLMSJV-UHFFFAOYSA-N
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Compound 4
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:HGCIXCUEYOPUTN-UHFFFAOYSA-N
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Compound 5
Molecular Weight:119.1207
Molecular Formula:C7H5NO
InChIKey:QUNPTMGXSSDZHZ-UHFFFAOYSA-N
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Compound 8
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 6
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 6a
Molecular Weight:111.0987
Molecular Formula:C5H5NO2
InChIKey:SEEYREPSKCQBBF-UHFFFAOYSA-N
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Compound 6b
Molecular Weight:125.1253
Molecular Formula:C6H7NO2
InChIKey:Not Available
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Compound 6c
Molecular Weight:139.1519
Molecular Formula:C7H9NO2
InChIKey:DABFKTHTXOELJF-UHFFFAOYSA-N
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Compound 6d
Molecular Weight:153.1784
Molecular Formula:C8H11NO2
InChIKey:JNPCNDJVEUEFBO-UHFFFAOYSA-N
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Compound 9
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:ZXABMDQSAABDMG-UHFFFAOYSA-N
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Compound 11
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:QUMSUJWRUHPEEJ-UHFFFAOYSA-N
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Compound 12
Molecular Weight:66.1011
Molecular Formula:C5H6
InChIKey:ZSWFCLXCOIISFI-UHFFFAOYSA-N
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Compound 13
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:FUSUHKVFWTUUBE-UHFFFAOYSA-N
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Compound 19a
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:FUSUHKVFWTUUBE-UHFFFAOYSA-N
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Compound 102
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:FUSUHKVFWTUUBE-UHFFFAOYSA-N
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Compound 14
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:NIMLCWCLVJRPFY-WGTSGOJVSA-N
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Compound 15
Molecular Weight:208.2552
Molecular Formula:C15H12O
InChIKey:Not Available
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Compound 16
Molecular Weight:333.3805
Molecular Formula:C21H19NO3
InChIKey:CAMIWKKHCMJHBV-UHFFFAOYSA-N
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Compound 17
Molecular Weight:188.1794
Molecular Formula:C11H8O3
InChIKey:DBDLTJRCKGCKSK-UHFFFAOYSA-N
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Compound 18
Molecular Weight:254.2806
Molecular Formula:C16H14O3
InChIKey:VEKVXTLHGZDHTJ-UHFFFAOYSA-N
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Compound 19
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 19b
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:Not Available
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Compound 20
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 20a
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:NIMLCWCLVJRPFY-WGTSGOJVSA-N
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Compound 20b
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:QPSCDHQKVFGRQM-WGTSGOJVSA-N
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Compound 21a
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:BAPJBEWLBFYGME-UHFFFAOYSA-N
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Compound 21b
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:JIGUQPWFLRLWPJ-UHFFFAOYSA-N
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Compound 21c
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:CQEYYJKEWSMYFG-UHFFFAOYSA-N
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Compound 22a
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:RMAZRAQKPTXZNL-KVARREAHSA-N
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Compound 22b
Molecular Weight:166.217
Molecular Formula:C10H14O2
InChIKey:FCCGTJAGEHZPBF-WGTSGOJVSA-N
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Compound 22c
Molecular Weight:194.2701
Molecular Formula:C12H18O2
InChIKey:RFIHUFUZAHTZOQ-JKIOLJMWSA-N
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Compound 23a
Molecular Weight:197.97
Molecular Formula:C6H11BF4N2
InChIKey:CUNYTRQQXKCRTJ-UHFFFAOYSA-N
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Compound 23b
Molecular Weight:284.1823
Molecular Formula:C8H15F6N2P
InChIKey:Not Available
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Compound 23c
Molecular Weight:322.2289
Molecular Formula:C12H23IN2
InChIKey:KRLZUNVVBLGDJV-UHFFFAOYSA-M
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Compound 21
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 22
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 25
Molecular Weight:82.1436
Molecular Formula:C6H10
InChIKey:SDJHPPZKZZWAKF-UHFFFAOYSA-N
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Compound 27
Molecular Weight:80.1277
Molecular Formula:C6H8
InChIKey:Not Available
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Compound 24
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 24a
Molecular Weight:177.1998
Molecular Formula:C10H11NO2
InChIKey:WHRYLXXHLFPFNZ-KVFPUHGPSA-N
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Compound 24b
Molecular Weight:191.2264
Molecular Formula:C11H13NO2
InChIKey:HDNAENGLYCLHFK-SPJNRGJMSA-N
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Compound 24c
Molecular Weight:205.253
Molecular Formula:C12H15NO2
InChIKey:RQGOXSVAQXFULZ-YNFQOJQRSA-N
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Compound 24d
Molecular Weight:219.2796
Molecular Formula:C13H17NO2
InChIKey:MYVFYVDFTPQNBY-DTIDVZRVSA-N
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Compound 26
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 26a
Molecular Weight:193.2423
Molecular Formula:C11H15NO2
InChIKey:KYDLJSYPTLTQOB-UHFFFAOYSA-N
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Compound 26b
Molecular Weight:207.2689
Molecular Formula:C12H17NO2
InChIKey:TTYUQVQPVPJGEA-UHFFFAOYSA-N
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Compound 26c
Molecular Weight:221.2955
Molecular Formula:C13H19NO2
InChIKey:RBSLXVLDXKEYPI-UHFFFAOYSA-N
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Compound 26d
Molecular Weight:235.322
Molecular Formula:C14H21NO2
InChIKey:MYQZWWXOGYVYCM-UHFFFAOYSA-N
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Compound 28
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 28a
Molecular Weight:191.2264
Molecular Formula:C11H13NO2
InChIKey:RLJWNHYAZXPZFE-SPJNRGJMSA-N
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Compound 28b
Molecular Weight:205.253
Molecular Formula:C12H15NO2
InChIKey:VXYZSJHPWNYHBZ-YNFQOJQRSA-N
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Compound 28c
Molecular Weight:219.2796
Molecular Formula:C13H17NO2
InChIKey:SDUHGAKOGFHFGR-DTIDVZRVSA-N
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Compound 28d
Molecular Weight:233.3062
Molecular Formula:C14H19NO2
InChIKey:VTJHMWVLZOPRKY-BKUVIOGVSA-N
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Compound 29
Molecular Weight:260.129
Molecular Formula:C13H10BrN
InChIKey:PIYWJWXEZWYQDR-UHFFFAOYSA-M
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Compound 30
Molecular Weight:326.23
Molecular Formula:C18H16BrN
InChIKey:MCRGNSYFHBSHMP-UHFFFAOYSA-M
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Compound 31a
Molecular Weight:209.1986
Molecular Formula:C10H11NO4
InChIKey:COKMFRAYOXGOHR-PLNGDYQASA-N
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Compound 31
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 31b
Molecular Weight:223.2252
Molecular Formula:C11H13NO4
InChIKey:RHVIADNOLIKWCG-WAYWQWQTSA-N
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Compound 31c
Molecular Weight:237.2518
Molecular Formula:C12H15NO4
InChIKey:UYLFTWHKWYDIJH-WAYWQWQTSA-N
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Compound 32
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 32a
Molecular Weight:209.1986
Molecular Formula:C10H11NO4
InChIKey:DSGNMFPBRAMEKL-NXHIJNRMSA-N
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Compound 32b
Molecular Weight:223.2252
Molecular Formula:C11H13NO4
InChIKey:MIHCRRSFJZJEPF-QMWUCLPTSA-N
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Compound 32c
Molecular Weight:237.2518
Molecular Formula:C12H15NO4
InChIKey:VAVSUFCIZJQGPX-HBXNBJCXSA-N
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Compound 33a
Molecular Weight:224.2546
Molecular Formula:C15H12O2
InChIKey:MVIKHPHEDJNFFN-UHFFFAOYSA-N
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Compound 33b
Molecular Weight:238.2812
Molecular Formula:C16H14O2
InChIKey:NELNWZJOZOSDFH-UHFFFAOYSA-N
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Compound 33
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 34
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 34a
Molecular Weight:158.1534
Molecular Formula:C10H6O2
InChIKey:FRASJONUBLZVQX-UHFFFAOYSA-N
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Compound 34b
Molecular Weight:172.18
Molecular Formula:C11H8O2
InChIKey:MJVAVZPDRWSRRC-UHFFFAOYSA-N
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Compound 35
Molecular Weight:236.2321
Molecular Formula:C12H8N6
InChIKey:Not Available
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Compound 36a
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:UAJRSHJHFRVGMG-UHFFFAOYSA-N
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Compound 36b
Molecular Weight:118.1757
Molecular Formula:C9H10
InChIKey:JLBJTVDPSNHSKJ-UHFFFAOYSA-N
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Compound 36c
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-UHFFFAOYSA-N
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Compound 36d
Molecular Weight:138.594
Molecular Formula:C8H7Cl
InChIKey:KTZVZZJJVJQZHV-UHFFFAOYSA-N
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Compound 36e
Molecular Weight:149.1467
Molecular Formula:C8H7NO2
InChIKey:YFZHODLXYNDBSM-UHFFFAOYSA-N
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Compound 36
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 37
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 37a
Molecular Weight:370.4072
Molecular Formula:C21H18N6O
InChIKey:PGXRUMRZUCFBJZ-UHFFFAOYSA-N
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Compound 37b
Molecular Weight:354.4078
Molecular Formula:C21H18N6
InChIKey:PUWBDDKNKAOWIR-UHFFFAOYSA-N
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Compound 37c
Molecular Weight:340.3812
Molecular Formula:C20H16N6
InChIKey:AZQOIIOQQAPSHO-UHFFFAOYSA-N
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Compound 37d
Molecular Weight:374.826
Molecular Formula:C20H15ClN6
InChIKey:ZQMLLVLJPCUFIN-UHFFFAOYSA-N
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Compound 37e
Molecular Weight:385.3788
Molecular Formula:C20H15N7O2
InChIKey:GSFHZKAPHDTGGG-UHFFFAOYSA-N
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Compound 38
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 38a
Molecular Weight:342.3938
Molecular Formula:C21H18N4O
InChIKey:ZGDVRBNIVYLUQI-UHFFFAOYSA-N
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Compound 38b
Molecular Weight:326.3944
Molecular Formula:C21H18N4
InChIKey:HKQOMMLFLYFLEJ-UHFFFAOYSA-N
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Compound 38c
Molecular Weight:312.3678
Molecular Formula:C20H16N4
InChIKey:JWSPJORILSYSHX-UHFFFAOYSA-N
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Compound 38d
Molecular Weight:346.813
Molecular Formula:C20H15ClN4
InChIKey:KHNQIBSJPANQKT-UHFFFAOYSA-N
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Compound 38e
Molecular Weight:357.3654
Molecular Formula:C20H15N5O2
InChIKey:LOQURAUCFANTOX-UHFFFAOYSA-N
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Compound 39
Molecular Weight:74.0355
Molecular Formula:C2H2O3
InChIKey:Not Available
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Compound 41
Molecular Weight:Not Available
Molecular Formula:(CH2)nC6H6O3
InChIKey:LOTRXPYWDQSASJ-JKUQZMGJSA-N
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Compound 42
Molecular Weight:Not Available
Molecular Formula:(CH2)nC6H6O3
InChIKey:LOTRXPYWDQSASJ-KVQBGUIXSA-N
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Compound 41a
Molecular Weight:140.1366
Molecular Formula:C7H8O3
InChIKey:LOTRXPYWDQSASJ-JKUQZMGJSA-N
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Compound 41b
Molecular Weight:154.1632
Molecular Formula:C8H10O3
InChIKey:CVSZHDPJIGWVDS-XVMARJQXSA-N
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Compound 42a
Molecular Weight:140.1366
Molecular Formula:C7H8O3
InChIKey:LOTRXPYWDQSASJ-KVQBGUIXSA-N
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Compound 42b
Molecular Weight:154.1632
Molecular Formula:C8H10O3
InChIKey:CVSZHDPJIGWVDS-RRKCRQDMSA-N
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Compound 44
Molecular Weight:177.1998
Molecular Formula:C10H11NO2
InChIKey:WHRYLXXHLFPFNZ-KVFPUHGPSA-N
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Compound 45
Molecular Weight:107.1531
Molecular Formula:C7H9N
InChIKey:WGQKYBSKWIADBV-UHFFFAOYSA-N
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Compound 43
Molecular Weight:221.726
Molecular Formula:C13H16ClN
InChIKey:KKOLKWYYYTYFMI-JHEYCYPBSA-N
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Compound 47
Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:IPJZLMDAZVIIRQ-MNOVXSKESA-N
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Compound 48
Molecular Weight:107.11
Molecular Formula:C6H5NO
InChIKey:NLRKCXQQSUWLCH-UHFFFAOYSA-N
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Compound 49
Molecular Weight:180.2451
Molecular Formula:C14H12
InChIKey:PJANXHGTPQOBST-VAWYXSNFSA-N
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Compound 50
Molecular Weight:360.4902
Molecular Formula:C28H24
InChIKey:RJWNMNWMVUOVHV-PCYFZWJMSA-N
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Compound 51
Molecular Weight:360.4902
Molecular Formula:C28H24
InChIKey:RJWNMNWMVUOVHV-HCOFYKJDSA-N
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Compound 52
Molecular Weight:178.2292
Molecular Formula:C14H10
InChIKey:YNPNZTXNASCQKK-UHFFFAOYSA-N
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Compound 53
Molecular Weight:146.1427
Molecular Formula:C9H6O2
InChIKey:ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
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Compound 54
Molecular Weight:292.2855
Molecular Formula:C18H12O4
InChIKey:LLDOJHIQWQQUIQ-GEEKYZPCSA-N
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Compound 55
Molecular Weight:292.2855
Molecular Formula:C18H12O4
InChIKey:LLDOJHIQWQQUIQ-KLHDSHLOSA-N
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Compound 56
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:JFNLZVQOOSMTJK-KNVOCYPGSA-N
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Compound 57
Molecular Weight:119.124
Molecular Formula:C6H5N3
InChIKey:CTRLRINCMYICJO-UHFFFAOYSA-N
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Compound 58
Molecular Weight:211.2624
Molecular Formula:C13H13N3
InChIKey:YOXMBMWYYHTTLH-JULQROHOSA-N
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Compound 59
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:LPIQUOYDBNQMRZ-UHFFFAOYSA-N
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Compound 60
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:JKTCBAGSMQIFNL-UHFFFAOYSA-N
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Compound 61
Molecular Weight:53.0626
Molecular Formula:C3H3N
InChIKey:NLHHRLWOUZZQLW-UHFFFAOYSA-N
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Compound 63
Molecular Weight:187.2377
Molecular Formula:C12H13NO
InChIKey:YKPVEVKUGPWDID-UHFFFAOYSA-N
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Compound 62
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 64
Molecular Weight:197.2325
Molecular Formula:C13H11NO
InChIKey:ZEAUJQWDPKRESH-KAMYIIQDSA-N
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Compound 65
Molecular Weight:228.2848
Molecular Formula:C12H20O4
InChIKey:JBSLOWBPDRZSMB-BQYQJAHWSA-N
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Compound 66
Molecular Weight:425.5173
Molecular Formula:C25H31NO5
InChIKey:QHSDJDPIYQTQRG-VNXZQDSDSA-N
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Compound 67
Molecular Weight:142.1127
Molecular Formula:C5H6N2O3
InChIKey:JFADAFQNHSDFKQ-UHFFFAOYSA-N
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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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 70
Molecular Weight:210.1845
Molecular Formula:C10H12O5
InChIKey:WYUCBTGONBSWLT-HTRCEHHLSA-L
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Compound 71
Molecular Weight:210.1845
Molecular Formula:C10H12O5
InChIKey:DCYFFRFUXITMHP-WKFQBHICSA-L
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Compound 72a
Molecular Weight:226.312
Molecular Formula:C13H22O3
InChIKey:OXTYENDIQSMPHP-UHFFFAOYSA-N
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Compound 72b
Molecular Weight:234.2672
Molecular Formula:C12H19NaO3
InChIKey:QNTDFDFNCWNAFX-UHFFFAOYSA-M
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Compound 72
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 73
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 73a
Molecular Weight:226.312
Molecular Formula:C13H22O3
InChIKey:NOLYALCPLHQVPK-GQCTYLIASA-N
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Compound 73b
Molecular Weight:234.2672
Molecular Formula:C12H19NaO3
InChIKey:VSLKIVHVQMQECT-WGCWOXMQSA-M
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Compound 74
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:Not Available
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Compound 75
Molecular Weight:146.1014
Molecular Formula:C4H6N2O4
InChIKey:NCBFTYFOPLPRBX-AATRIKPKSA-N
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Compound 76
Molecular Weight:238.2399
Molecular Formula:C11H14N2O4
InChIKey:WITQEHXYNZSTPS-OJOKCITNSA-N
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Compound 77a
Molecular Weight:209.2432
Molecular Formula:C14H11NO
InChIKey:UYYLCENCUQKANA-MDZDMXLPSA-N
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Compound 77b
Molecular Weight:254.2408
Molecular Formula:C14H10N2O3
InChIKey:ABZNBGWNJJAEIN-RMKNXTFCSA-N
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Compound 77c
Molecular Weight:239.2692
Molecular Formula:C15H13NO2
InChIKey:GFHMCCZEIHMATM-JXMROGBWSA-N
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Compound 79
Molecular Weight:209.2432
Molecular Formula:C14H11NO
InChIKey:SVMJUKBSJNQUFP-VOTSOKGWSA-N
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Compound 81
Molecular Weight:200.1901
Molecular Formula:C12H8O3
InChIKey:WFMIAEHBCQQOPZ-UHFFFAOYSA-N
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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 78a
Molecular Weight:275.3444
Molecular Formula:C19H17NO
InChIKey:ITLBWWBLBQJKTH-WWXIPJKBSA-N
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Compound 78b
Molecular Weight:320.3419
Molecular Formula:C19H16N2O3
InChIKey:ATZTXWULRWKOPN-LHVTWPBJSA-N
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Compound 78c
Molecular Weight:305.3704
Molecular Formula:C20H19NO2
InChIKey:LDCXYBSJYXOFEP-OMGLFLRBSA-N
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Compound 80
Molecular Weight:275.3444
Molecular Formula:C19H17NO
InChIKey:WLUQMVLXWKQPGQ-VEZWFGLTSA-N
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Compound 82
Molecular Weight:266.2913
Molecular Formula:C17H14O3
InChIKey:UYJBVRXWCMSGGO-UHFFFAOYSA-N
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Compound 83
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:LNRUJSUKKBJFOM-UHFFFAOYSA-N
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Compound 84
Molecular Weight:298.3331
Molecular Formula:C18H18O4
InChIKey:RNPUHLBIBANJIR-UHFFFAOYSA-N
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Compound 85
Molecular Weight:298.3331
Molecular Formula:C18H18O4
InChIKey:LQEVXCNJTYXCFY-UHFFFAOYSA-N
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Compound 86
Molecular Weight:184.2371
Molecular Formula:C12H12N2
InChIKey:NBPGPQJFYXNFKN-UHFFFAOYSA-N
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Compound 87a
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:UDJYVJWCIAORAU-UHFFFAOYSA-N
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Compound 87b
Molecular Weight:180.2435
Molecular Formula:C11H16O2
InChIKey:RUKQCQHJAIMHTH-UHFFFAOYSA-N
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Compound 87c
Molecular Weight:256.384
Molecular Formula:C12H16O2S2
InChIKey:HKHDNVPGDSIVEM-UHFFFAOYSA-N
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Compound 87d
Molecular Weight:240.2955
Molecular Formula:C13H20O4
InChIKey:LHYVPTHCKAHLTM-UHFFFAOYSA-N
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Compound 88a
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:XGMVPAINDHXJMY-BGZDPUMWSA-N
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Compound 88b
Molecular Weight:180.2435
Molecular Formula:C11H16O2
InChIKey:KUBCJWBKELGNFP-SJQPAMGKSA-N
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Compound 88c
Molecular Weight:256.384
Molecular Formula:C12H16O2S2
InChIKey:UVRXAJVPWAYNEK-VLEAKVRGSA-N
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Compound 88d
Molecular Weight:240.2955
Molecular Formula:C13H20O4
InChIKey:NSQIPUDYPVXDMP-USZNOCQGSA-N
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Compound 89a
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:XGMVPAINDHXJMY-MWBBWYEJSA-N
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Compound 89b
Molecular Weight:180.2435
Molecular Formula:C11H16O2
InChIKey:KUBCJWBKELGNFP-DYKKXSAXSA-N
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Compound 89c
Molecular Weight:256.384
Molecular Formula:C12H16O2S2
InChIKey:UVRXAJVPWAYNEK-IXMYILBSSA-N
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Compound 89d
Molecular Weight:240.2955
Molecular Formula:C13H20O4
InChIKey:NSQIPUDYPVXDMP-MBYGNEARSA-N
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Compound 88
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 89
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 99
Molecular Weight:68.117
Molecular Formula:C5H8
InChIKey:RRHGJUQNOFWUDK-UHFFFAOYSA-N
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Compound 90
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:MEIRRNXMZYDVDW-MQQKCMAXSA-N
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Compound 91
Molecular Weight:220.15
Molecular Formula:C9H18BrN
InChIKey:OWRYKPDXGVGJIO-YWEMJPMZSA-M
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Compound 92
Molecular Weight:1010.924
Molecular Formula:C54H108CuO8P2
InChIKey:ITANFFNAZVPUJJ-UHFFFAOYSA-L
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Compound 93
Molecular Weight:198.3019
Molecular Formula:C12H22O2
InChIKey:MDYPDLBFDATSCF-UHFFFAOYSA-N
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Compound 94
Molecular Weight:420.155
Molecular Formula:C25H54ClNO
InChIKey:DJMBUOSDRGZRGR-UQIIZPHYSA-M
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Compound 95
Molecular Weight:525.689
Molecular Formula:C23H48INSSi
InChIKey:CPOMQGMUUDSJLI-UHFFFAOYSA-M
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Compound 96
Molecular Weight:450.451
Molecular Formula:C21H40BrNO4
InChIKey:LGYMHETVRHZPRO-GEEYTBSJSA-M
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Compound 97
Molecular Weight:978.155
Molecular Formula:C44H90BrIN2O4SSi
InChIKey:IJTZEWRHAFKDAW-MZWBYVBESA-L
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Compound 98
Molecular Weight:978.155
Molecular Formula:C44H90BrIN2O4SSi
InChIKey:SAACGARASQSZMV-MZWBYVBESA-L
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Compound 101
Molecular Weight:142.271
Molecular Formula:C7H14OSi
InChIKey:Not Available
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Compound 106
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:MLUCVPSAIODCQM-NSCUHMNNSA-N
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Compound 100
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:KOCUMXQOUWPSLK-SNAWJCMRSA-N
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Compound 103
Molecular Weight:56.0633
Molecular Formula:C3H4O
InChIKey:HGINCPLSRVDWNT-UHFFFAOYSA-N
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Compound 104
Molecular Weight:108.0948
Molecular Formula:C6H4O2
InChIKey:AZQWKYJCGOJGHM-UHFFFAOYSA-N
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Compound 105
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:BAPJBEWLBFYGME-UHFFFAOYSA-N
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Compound 107a
Molecular Weight:287.2674
Molecular Formula:C15H13NO5
InChIKey:LAQUSGABDKJNSQ-UHFFFAOYSA-N
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Compound 107b
Molecular Weight:301.294
Molecular Formula:C16H15NO5
InChIKey:RBCOQFZKCWBILT-UHFFFAOYSA-N
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Compound 107c
Molecular Weight:335.3533
Molecular Formula:C20H17NO4
InChIKey:KHYGLGQZCGVAIM-UHFFFAOYSA-N
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Compound 6f
Molecular Weight:173.1681
Molecular Formula:C10H7NO2
InChIKey:HIDBROSJWZYGSZ-UHFFFAOYSA-N
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Compound 108a
Molecular Weight:465.4553
Molecular Formula:C24H23N3O7
InChIKey:VFHPLKIOEIDVBZ-AGZIMHANSA-N
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Compound 108b
Molecular Weight:507.5351
Molecular Formula:C27H29N3O7
InChIKey:UTVIQNLIZVHDOU-VQQXNAOJSA-N
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Compound 108c
Molecular Weight:637.6799
Molecular Formula:C39H31N3O6
InChIKey:XFHXBDMGQQWZAS-MOPRREJQSA-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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