Standard Article

Reactivity of Oxiranes with Organolithium Reagents

Organolithium Compounds (2004)

  1. Fabrice Chemla,
  2. Emmanuel Vrancken

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0314

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Chemla, F. and Vrancken, E. 2009. Reactivity of Oxiranes with Organolithium Reagents. Patai's Chemistry of Functional Groups. .

Author Information

  1. Université Pierre et Marie Curie, Tour 44-45 2ème étage, Bte 183, Laboratoire de Chimie Organique, Paris Cedex 05, France

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    General Introduction
  • 2
    α-/β-Deprotonation
  • 3
    β-Deprotonation
  • 4
    Oxirane Ring Opening by Organolithium Reagents
  • 5
    Synthesis and Reactivity of Lithiooxiranes
  • 6
    General Conclusion
  • 7
    Acknowledgments

Keywords:

  • oxirane reactivity with organolithium reagents;
  • β-deprotonation reaction and oxirane isomerization normal mode;
  • enantioselective access to allylic alcohols via asymmetric rearrangement;
  • proton transfer rate between highly electronegative atoms;
  • DBU role on enantioselectivity;
  • organolithium reagent and oxirane ring opening;
  • oxirane enantioselective nucleophilic opening;
  • lithiooxirane synthesis and reactivity

Featured Compounds

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  1. 1 - 202
Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 51
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound 52
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound 4
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:LVDALGYBEFALAP-NXEZZACHSA-N
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Compound 5
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:PQANGXXSEABURG-UHFFFAOYSA-N
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Compound 6
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:Not Available
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Compound 7
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 10
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 11
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 12
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 14
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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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 13
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 17
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:OHNNZOOGWXZCPZ-UHFFFAOYSA-N
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Compound 18
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:OZMQKGXJENMAHL-UHFFFAOYSA-N
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Compound 19
Molecular Weight:130.2244
Molecular Formula:C8H16O
InChIKey:Not Available
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Compound 20
Molecular Weight:130.2244
Molecular Formula:C8H16O
InChIKey:Not Available
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Compound 21
Molecular Weight:130.2244
Molecular Formula:C8H16O
InChIKey:Not Available
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Compound 151
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:PSBABBDEUFNFKJ-UHFFFAOYSA-N
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Compound 24
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:MELPJGOMEMRMPL-UHFFFAOYSA-N
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Compound 163
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:MELPJGOMEMRMPL-UHFFFAOYSA-N
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Compound 35
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:RBACIKXCRWGCBB-UHFFFAOYSA-N
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Compound 22
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 23
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 25
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:AOONMBCPMGBOBG-PRJMDXOYSA-N
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Compound 26
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:UJZBDMYKNUWDPM-XQRVVYSFSA-N
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Compound 27
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 28
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 29
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 30
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 31
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 32
Molecular Weight:155.2555
Molecular Formula:C10H18O
InChIKey:Not Available
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Compound 33
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:OOEPVZSVTNDRRX-BDAKNGLRSA-N
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Compound 34
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:JFDMLXYWGLECEY-UHFFFAOYSA-N
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Compound 36
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:BWERZOKUEPUTTM-XHNCKOQMSA-N
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Compound 37
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:NGXNAIZTJAUMGV-IUCAKERBSA-N
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Compound 38
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:OOEPVZSVTNDRRX-RKDXNWHRSA-N
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Compound 39
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:OQOKLVGYVIWSPZ-OXYCZDQYSA-N
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Compound 40
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:FSJWHFQEMOTPAZ-RTBKNWGFSA-N
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Compound 41
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:FSJWHFQEMOTPAZ-UDNWOFFPSA-N
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Compound 42
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:SMTZVJAUYSVPIA-UHFFFAOYSA-N
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Compound 43
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:CRVVQFBWAMRUEO-UHFFFAOYSA-N
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Compound 44
Molecular Weight:126.1962
Molecular Formula:C8H14O
InChIKey:FRHPIEBOJQGXAM-GORDUTHDSA-N
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Compound E-47
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Z-47
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 50
Molecular Weight:231.262
Molecular Formula:C16H18LiN
InChIKey:CYVKIOUCEFNHRY-IODNYQNNSA-N
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Compound 75
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:PQANGXXSEABURG-ZCFIWIBFSA-N
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Compound 53
Molecular Weight:160.186
Molecular Formula:C9H17LiN2
InChIKey:ZPVNYTWCCOIEDF-FVGYRXGTSA-N
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Compound 54
Molecular Weight:216.292
Molecular Formula:C13H25LiN2
InChIKey:XMVOMUKIAZVPPI-ZOWNYOTGSA-N
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Compound 55
Molecular Weight:214.276
Molecular Formula:C13H23LiN2
InChIKey:QKBRPLJBUBJSNB-QKWXXBCPSA-N
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Compound 56
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 56a
Molecular Weight:186.223
Molecular Formula:C11H19LiN2
InChIKey:BRZWTYFTMSTTIZ-FHGSKDHASA-N
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Compound 56b
Molecular Weight:214.276
Molecular Formula:C13H23LiN2
InChIKey:MBCITDDMRIHVNM-XECDSOBRSA-N
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Compound 57
Molecular Weight:289.341
Molecular Formula:C19H24LiNO
InChIKey:UXXGFUASBHLZJK-GRTNUQQKSA-N
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Compound 58
Molecular Weight:224.271
Molecular Formula:C14H21LiN2
InChIKey:GOIOTYAEJOXRHO-UQKRIMTDSA-N
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Compound 59
Molecular Weight:224.271
Molecular Formula:C14H21LiN2
InChIKey:QETMVBVFWMLHHE-KYSPHBLOSA-N
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Compound 60
Molecular Weight:358.6635
Molecular Formula:C18H38O3Si2
InChIKey:YHSHEKUBOZESPG-GEEKYZPCSA-N
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Compound 61
Molecular Weight:224.271
Molecular Formula:C14H21LiN2
InChIKey:QETMVBVFWMLHHE-DSHXVJGRSA-N
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Compound 62
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 63
Molecular Weight:88.037
Molecular Formula:C4H5LiN2
InChIKey:PGGUIZNCKIWWBO-UHFFFAOYSA-N
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Compound 64
Molecular Weight:102.063
Molecular Formula:C5H7LiN2
InChIKey:XEMXLYFQSAJHAR-UHFFFAOYSA-N
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Compound 65
Molecular Weight:194.222
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 67
Molecular Weight:158.17
Molecular Formula:C9H15LiN2
InChIKey:SMFLHGNJJJRRIJ-UHFFFAOYSA-N
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Compound 68
Molecular Weight:382.441
Molecular Formula:C23H36Li2N4
InChIKey:JTZCBKOYYRJBJE-CIVWOOMMSA-N
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Compound 69
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:CWRSDAPNEGDROZ-ZSBIGDGJSA-N
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Compound 70
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:YRZMGHLEACVCDU-NWDGAFQWSA-N
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Compound 71
Molecular Weight:163.072
Molecular Formula:C9H11Li2NO
InChIKey:VSGCHBCRFRABCA-VZIDAPDWSA-N
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Compound 72a
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:ZWMXHPOWONDHGL-FPFOFBBKSA-N
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Compound 73a
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:POCJXFOZRKCVMA-NTSWFWBYSA-N
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Compound 72
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 72b
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:GFXYVXUYCSWWMJ-ZMONIFLSSA-N
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Compound 72c
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:ASVMVSOGDKJSET-MYJAWHEDSA-N
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Compound 73
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 73b
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:IDWWUCXOGPDLEV-RQJHMYQMSA-N
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Compound 73c
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:BLFULFONVUXPQH-ZJUUUORDSA-N
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Compound 74
Molecular Weight:242.213
Molecular Formula:C12H24Li2N2O2
InChIKey:CNKPMVXFEGSVGW-MBORUXJMSA-N
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Compound 76
Molecular Weight:138.2499
Molecular Formula:C10H18
InChIKey:IOERJMOJJLOARF-SECBINFHSA-N
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Compound 77
Molecular Weight:156.2652
Molecular Formula:C10H20O
InChIKey:HSTMKGFYRGMMOF-XVBQNVSMSA-N
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Compound 78
Molecular Weight:386.7167
Molecular Formula:C20H42O3Si2
InChIKey:BLAWJFOREIWNQS-FZDBZEDMSA-N
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Compound 79
Molecular Weight:386.7167
Molecular Formula:C20H42O3Si2
InChIKey:NTQWFRZQFJXUTM-ZBRFXRBCSA-N
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Compound 80
Molecular Weight:386.7167
Molecular Formula:C20H42O3Si2
InChIKey:HGTXLVFMCDMVLP-GCNJGVOGSA-N
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Compound 81
Molecular Weight:294.4323
Molecular Formula:C17H30N2O2
InChIKey:PIJFQTUSLZLNOP-ZIAGYGMSSA-N
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Compound 112
Molecular Weight:234.3803
Molecular Formula:C15H26N2
InChIKey:SLRCCWJSBJZJBV-ZQDZILKHSA-N
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Compound 82
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:OXVVSBWVXAHVJR-DOFRTFSJSA-N
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Compound 89
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:Not Available
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Compound 167
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:Not Available
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Compound 83
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:YWFPXWMSGJXUFS-UPHRSURJSA-N
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Compound 172
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:GAJWLWOIFZSYOW-BFZCNVHISA-N
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Compound 84
Molecular Weight:244.2842
Molecular Formula:C12H20O5
InChIKey:WWRGCMXVXRWPPT-YBXAARCKSA-N
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Compound 85
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:LVUQVFWOWNKFRL-SSDOTTSWSA-N
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Compound 86
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:NFLGAXVYCFJBMK-IUCAKERBSA-N
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Compound 140
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:YVCOJTATJWDGEU-UHFFFAOYSA-N
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Compound 87
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:GXBYFVGCMPJVJX-UHFFFAOYSA-N
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Compound 88
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:Not Available
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Compound 90
Molecular Weight:84.1164
Molecular Formula:C5H8O
InChIKey:FVCDMHWSPLRYAB-UHFFFAOYSA-N
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Compound 91
Molecular Weight:184.3507
Molecular Formula:C10H20OSi
InChIKey:BUNJYYVBMJGLGP-IUCAKERBSA-N
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Compound 92
Molecular Weight:126.169
Molecular Formula:C4H7LiS2
InChIKey:SSLUBYUKDKZZPS-UHFFFAOYSA-N
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Compound 93
Molecular Weight:510.289
Molecular Formula:C17H7F12LiS2
InChIKey:UCKYZTUHCMNTNO-UHFFFAOYSA-N
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Compound 94
Molecular Weight:238.297
Molecular Formula:C13H11LiS2
InChIKey:BROZXTIQIWIXKJ-UHFFFAOYSA-N
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Compound 92a
Molecular Weight:198.351
Molecular Formula:C7H15LiS2Si
InChIKey:WNEZFWYVBVVCNA-UHFFFAOYSA-N
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Compound 92b
Molecular Weight:202.265
Molecular Formula:C10H11LiS2
InChIKey:GOXJKCHXKMYZIF-UHFFFAOYSA-N
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Compound 92c
Molecular Weight:154.223
Molecular Formula:C6H11LiS2
InChIKey:LMWFPVHLBRQFAK-UHFFFAOYSA-N
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Compound 92d
Molecular Weight:168.249
Molecular Formula:C7H13LiS2
InChIKey:IWOUUCTYQKQIFT-UHFFFAOYSA-N
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Compound 92e
Molecular Weight:282.51
Molecular Formula:C13H27LiS2Si
InChIKey:RBUWCDKBCPBPKD-UHFFFAOYSA-N
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Compound 95
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 96
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:XXYWCMMODULAAA-ONGXEEELSA-N
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Compound 97
Molecular Weight:190.326
Molecular Formula:C8H14OS2
InChIKey:JUDIOQYSYPXCIS-BQBZGAKWSA-N
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Compound 98
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 142
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:KRIOVPPHQSLHCZ-UHFFFAOYSA-N
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Compound 99
Molecular Weight:217.234
Molecular Formula:C12H20LiNO2
InChIKey:PHMUHRMTQFOZRM-MHDYBILJSA-M
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Compound 100
Molecular Weight:169.076
Molecular Formula:C8H13Li2NO2
InChIKey:ODZPFDNAGNZPDK-AGKQHHPUSA-M
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Compound 101
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:LSADSZGYXFMATO-NEPJUHHUSA-N
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Compound 102
Molecular Weight:380.4752
Molecular Formula:C21H32O6
InChIKey:ULGVJSDQAXXESA-BVBHFADKSA-N
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Compound 103
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 104
Molecular Weight:327.346
Molecular Formula:C21H22LiNO2
InChIKey:ICYRGAJIHXQFDM-MMJFVAIHSA-M
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Compound 105
Molecular Weight:92.524
Molecular Formula:C3H5ClO
InChIKey:BRLQWZUYTZBJKN-GSVOUGTGSA-N
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Compound 106
Molecular Weight:263.3321
Molecular Formula:C15H21NO3
InChIKey:NVPOUMXZERMIJK-STQMWFEESA-N
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Compound 107
Molecular Weight:333.5081
Molecular Formula:C21H35NO2
InChIKey:HVLXUTVRWKYBJV-USCXLKSCSA-N
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Compound 108
Molecular Weight:277.4018
Molecular Formula:C17H27NO2
InChIKey:GKNQQJKZIFHQPI-YFEUJDIGSA-N
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Compound 110
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 111
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 113
Molecular Weight:364.3912
Molecular Formula:C22H20O5
InChIKey:XKONAJBSSOKGFV-HGNWCAPWSA-N
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Compound 114
Molecular Weight:364.3912
Molecular Formula:C22H20O5
InChIKey:XKONAJBSSOKGFV-RJSBPICXSA-N
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Compound 115
Molecular Weight:370.324
Molecular Formula:C22H19LiO5
InChIKey:JFZHGKRWEZOOOV-HVNMXSENSA-N
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Compound 116
Molecular Weight:370.324
Molecular Formula:C22H19LiO5
InChIKey:JFZHGKRWEZOOOV-RRSSWADWSA-N
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Compound 118
Molecular Weight:274.207
Molecular Formula:C15H14F3LiO
InChIKey:GSXZMHFNHJJXES-UQKRIMTDSA-N
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Compound 117
Molecular Weight:283.074
Molecular Formula:C11H7Cl2F3O
InChIKey:ZDWOHJIBXCKCLJ-UHFFFAOYSA-N
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Compound 119
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 121
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 123
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 124
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 125
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 127
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 128
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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 132
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 133
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:QIQQIUPZGCZKOB-UHFFFAOYSA-N
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Compound 134
Molecular Weight:174.239
Molecular Formula:C12H14O
InChIKey:SEKQECDUSDIAPN-UHFFFAOYSA-N
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Compound 135
Molecular Weight:158.2775
Molecular Formula:C10H20O
InChIKey:Not Available
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Compound 136
Molecular Weight:157.2714
Molecular Formula:C10H20O
InChIKey:Not Available
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Compound 137
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:OHWMCUHFWPORRH-UHFFFAOYSA-N
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Compound 138
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:VDQFEVQCXBWMII-UHFFFAOYSA-N
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Compound 139
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:BOVGSYBYODIBGS-ARJAWSKDSA-N
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Compound 141
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:MHHJQVRGRPHIMR-UHFFFAOYSA-N
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Compound 143
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:QCCDLTOVEPVEJK-UHFFFAOYSA-N
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Compound 144
Molecular Weight:242.4298
Molecular Formula:C13H26O2Si
InChIKey:ATHKEDHFMAZPQG-ZSBIGDGJSA-N
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Compound 145
Molecular Weight:242.4298
Molecular Formula:C13H26O2Si
InChIKey:ATHKEDHFMAZPQG-CNDDSTCGSA-N
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Compound S-146
Molecular Weight:242.4298
Molecular Formula:C13H26O2Si
InChIKey:VWZXUWFQADLMIK-LBPRGKRZSA-N
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Compound R-146
Molecular Weight:242.4298
Molecular Formula:C13H26O2Si
InChIKey:VWZXUWFQADLMIK-GFCCVEGCSA-N
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Compound 147
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:RAVWLTJDSSKYGK-UHFFFAOYSA-N
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Compound 148
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:OHNNZOOGWXZCPZ-UHFFFAOYSA-N
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Compound 149
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:RDWPVMYJNZOZPT-UHFFFAOYSA-N
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Compound 150
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:XYBMDMJEJFCMFT-UHFFFAOYSA-N
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Compound 152
Molecular Weight:112.1298
Molecular Formula:C5H8N2O
InChIKey:GRAFXUITHXLFDJ-UHFFFAOYSA-N
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Compound 153
Molecular Weight:118.063
Molecular Formula:C5H7LiN2O
InChIKey:KMILGHGKIHGWHW-UHFFFAOYSA-N
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Compound 155
Molecular Weight:90.049
Molecular Formula:C5H7LiO
InChIKey:ZMAPEDBHKMKEKU-UHFFFAOYSA-N
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Compound 156
Molecular Weight:176.182
Molecular Formula:C10H17LiO2
InChIKey:XSOPUUJBUUDXEI-OAINAWNSSA-N
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Compound 157
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:SHRWKGXPNYYGGO-UHFFFAOYSA-N
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Compound 158
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:LNRXJLKDTCWCEI-UHFFFAOYSA-N
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Compound 159
Molecular Weight:176.182
Molecular Formula:C10H17LiO2
InChIKey:UDDRIEGGIRIPOE-RIHXGJNQSA-N
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Compound 160
Molecular Weight:182.115
Molecular Formula:C10H16Li2O2
InChIKey:NUCHBBJIOZVUNC-JXGSBULDSA-N
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Compound 161
Molecular Weight:182.115
Molecular Formula:C10H16Li2O2
InChIKey:VUKZQIMUXLFMRU-NKRBYZSKSA-N
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Compound 162
Molecular Weight:182.115
Molecular Formula:C10H16Li2O2
InChIKey:JIQSSZMAFRUNFU-NKRBYZSKSA-N
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Compound 164
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:AFCZSFUPWLSMSZ-UHFFFAOYSA-N
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Compound 165
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:AFCZSFUPWLSMSZ-UHFFFAOYSA-N
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Compound 166
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:NWSDLEBQGQVEKA-RNJXMRFFSA-N
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Compound 168
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:LPILXVRHOMAVFE-BIIVOSGPSA-N
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Compound 169
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 170
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 171
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 173
Molecular Weight:234.3803
Molecular Formula:C15H26N2
InChIKey:SLRCCWJSBJZJBV-BYNSBNAKSA-N
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Compound 174
Molecular Weight:350.5386
Molecular Formula:C21H38N2O2
InChIKey:LWZYINOQCGJLML-QZTJIDSGSA-N
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Compound 175
Molecular Weight:194.3165
Molecular Formula:C12H22N2
InChIKey:JHVZGAIDVLLSEV-MCIGGMRASA-N
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Compound 176
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 177a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 177b
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:JPYJRMUJWOZZIG-DCAQKATOSA-N
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Compound 178a
Molecular Weight:174.1944
Molecular Formula:C8H14O4
InChIKey:SVLHZXHLCGLAFA-KVFPUHGPSA-N
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Compound 178b
Molecular Weight:174.1944
Molecular Formula:C8H14O4
InChIKey:SVLHZXHLCGLAFA-SOSBWXJGSA-N
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Compound 179
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 181
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 182
Molecular Weight:304.4541
Molecular Formula:C20H18OSi
InChIKey:Not Available
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Compound 183
Molecular Weight:316.4684
Molecular Formula:C21H20OSi
InChIKey:YYOJHPYKZOSDRV-LAUBAEHRSA-N
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Compound 184
Molecular Weight:228.4463
Molecular Formula:C13H28OSi
InChIKey:JVRWBVQTNCPSTP-OLZOCXBDSA-N
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Compound 185
Molecular Weight:228.4463
Molecular Formula:C13H28OSi
InChIKey:JVRWBVQTNCPSTP-CHWSQXEVSA-N
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Compound 186
Molecular Weight:142.271
Molecular Formula:C7H14OSi
InChIKey:CLAAUPGTFNCPAU-RQJHMYQMSA-N
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Compound 187
Molecular Weight:214.3767
Molecular Formula:C11H22O2Si
InChIKey:MQUBBMHBVPZDAP-NXEZZACHSA-N
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Compound 188
Molecular Weight:172.34
Molecular Formula:C9H20OSi
InChIKey:LOJGMFDGACBSEX-YUMQZZPRSA-N
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Compound 189
Molecular Weight:218.3654
Molecular Formula:C10H22O3Si
InChIKey:NOTVTJGMEDZONA-AGROOBSYSA-N
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Compound 190
Molecular Weight:224.2546
Molecular Formula:C15H12O2
InChIKey:UQGMJZQVDNZRKT-HUUCEWRRSA-N
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Compound 191
Molecular Weight:127.1842
Molecular Formula:C7H13NO
InChIKey:PPBIDOKOWNKFCP-KFGJBHQHSA-N
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Compound 192
Molecular Weight:254.3684
Molecular Formula:C14H26N2O2
InChIKey:XHVSWCSZKSTZQU-HPSXOYRMSA-N
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Compound 193
Molecular Weight:194.111
Molecular Formula:C8H11LiO5
InChIKey:SLJYFEUQCCTXMV-JEDNCBNOSA-N
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Compound 194
Molecular Weight:114.0993
Molecular Formula:C5H6O3
InChIKey:LWQJEOVXSWEZFZ-HZLVTQRSSA-N
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Compound 195
Molecular Weight:114.0993
Molecular Formula:C5H6O3
InChIKey:LWQJEOVXSWEZFZ-UZBSEBFBSA-N
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Compound 196
Molecular Weight:112.0505
Molecular Formula:C3H3F3O
InChIKey:AQZRARFZZMGLHL-UWTATZPHSA-N
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