Standard Article

Carbomagnesiation Reactions

Organomagnesium Compounds (2008)

  1. Kenichiro Itami1,
  2. Jun-Ichi Yoshida2

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0413

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Itami, K. and Yoshida, J.-I. 2009. Carbomagnesiation Reactions. Patai's Chemistry of Functional Groups. .

Author Information

  1. 1

    Nagoya University, Department of Chemistry and Research Center for Materials Science, Chikusa-ku, Nagoya, Japan

  2. 2

    Kyoto University, Graduate School of Engineering, Department of Synthetic Chemistry and Biological Chemistry, Nishikyo-ku, Kyoto, Japan

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    Introduction
  • 2
    Carbomagnesiation Reactions of Alkynes
  • 3
    Carbomagnesiation Reactions of Alkenes
  • 4
    Carbomagnesiation Reactions of Aromatics
  • 5
    Summary

Keywords:

  • carbomagnesiation reactions;
  • alkyne carbomagnesiation reaction;
  • alkynylsilane carbomagnesiation;
  • Tamao–Kumada–Corriu-type cross-coupling;
  • propargylic alcohols and regio- and stereoselective carbomagnesiation;
  • alkene carbomagnesiation reaction;
  • vinylsilane carbomagnesiation;
  • zirconium-catalyzed alkene ethylmagnesiation

Featured Compounds

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  1. 1 - 125
Compound 1
Molecular Weight:328.4052
Molecular Formula:C26H16
InChIKey:NVMYRXGXUBZAIU-UHFFFAOYSA-N
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Compound 2
Molecular Weight:178.2292
Molecular Formula:C14H10
InChIKey:ZYASLTYCYTYKFC-UHFFFAOYSA-N
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Compound 3
Molecular Weight:380.2217
Molecular Formula:C20H13I
InChIKey:BILHVIJKMJXZEC-UHFFFAOYSA-N
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Compound 4
Molecular Weight:254.3252
Molecular Formula:C20H14
InChIKey:RMQMLYMBZGDKBY-UHFFFAOYSA-N
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Compound 5
Molecular Weight:154.92
Molecular Formula:C7H11ClMg
InChIKey:AEOKPSVSBBSOPP-UHFFFAOYSA-M
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Compound 6
Molecular Weight:96.1702
Molecular Formula:C7H12
InChIKey:VONKRKBGTZDZNV-UHFFFAOYSA-N
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Compound 7
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 8
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:LVIRXIFRSKNRMQ-FPYGCLRLSA-N
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Compound 9
Molecular Weight:110.1968
Molecular Formula:C8H14
InChIKey:LVIRXIFRSKNRMQ-BAQGIRSFSA-N
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Compound 10
Molecular Weight:284.1361
Molecular Formula:C12H13I
InChIKey:WQHCLVHILIUEDL-UHFFFAOYSA-N
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Compound 11
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:UVDOIWXDCYNLJD-UHFFFAOYSA-N
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Compound 12
Molecular Weight:184.3184
Molecular Formula:C12H24O
InChIKey:NQHPXPNPPHMWNP-KHPPLWFESA-N
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Compound 13
Molecular Weight:168.2759
Molecular Formula:C11H20O
InChIKey:XHJCSFOTNWZUAD-UHFFFAOYSA-N
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Compound 15
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 17
Molecular Weight:216.3618
Molecular Formula:C16H24
InChIKey:CLABTEQPHNRONJ-OQLLNIDSSA-N
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Compound 18
Molecular Weight:266.3774
Molecular Formula:C19H22O
InChIKey:XTFKHKWLJOUFGN-OBGWFSINSA-N
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Compound 19
Molecular Weight:266.3774
Molecular Formula:C19H22O
InChIKey:XTFKHKWLJOUFGN-OBGWFSINSA-N
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Compound 20
Molecular Weight:266.3774
Molecular Formula:C19H22O
InChIKey:IWUQIDCEVFEQOO-YBFXNURJSA-N
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Compound 21
Molecular Weight:328.4468
Molecular Formula:C24H24O
InChIKey:MRAKWQCDJWGUNT-UHFFFAOYSA-N
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Compound 23
Molecular Weight:189.329
Molecular Formula:C11H15NSi
InChIKey:KRMLRFQSJRXDDB-UHFFFAOYSA-N
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Compound 24
Molecular Weight:267.4408
Molecular Formula:C17H21NSi
InChIKey:OYQMWAKBCFEDHT-CCEZHUSRSA-N
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Compound 25
Molecular Weight:189.329
Molecular Formula:C11H15NSi
InChIKey:XFCNVNVSFGYTCX-UHFFFAOYSA-N
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Compound 26
Molecular Weight:189.329
Molecular Formula:C11H15NSi
InChIKey:AXVSWDQTHGLTJJ-UHFFFAOYSA-N
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Compound 27
Molecular Weight:188.3409
Molecular Formula:C12H16Si
InChIKey:CPLRUWAVRDZCPQ-UHFFFAOYSA-N
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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:273.37
Molecular Formula:C17H23NO2
InChIKey:JECZSAZKSZGPEL-UHFFFAOYSA-N
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Compound 31
Molecular Weight:351.4819
Molecular Formula:C23H29NO2
InChIKey:QURZTQLGNQKKIG-ZBJSNUHESA-N
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Compound 32
Molecular Weight:369.52
Molecular Formula:C22H27NO2S
InChIKey:RKVMAPBFRSQGII-UHFFFAOYSA-N
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Compound 33
Molecular Weight:311.398
Molecular Formula:C18H17NO2S
InChIKey:RKCBYKORAHKJSJ-UHFFFAOYSA-N
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Compound 34
Molecular Weight:472.721
Molecular Formula:C22H26BrMgNO2S
InChIKey:NHPLLHFWCZJGLI-UHFFFAOYSA-M
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Compound 35
Molecular Weight:213.3181
Molecular Formula:C15H19N
InChIKey:BJOIIXBDWCCDDT-UHFFFAOYSA-N
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Compound 36
Molecular Weight:169.2209
Molecular Formula:C9H15NO2
InChIKey:NRJWYAOMEOATRK-UHFFFAOYSA-N
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Compound 37
Molecular Weight:227.3431
Molecular Formula:C13H25NO2
InChIKey:KYNBEHGAQYIXDK-MDZDMXLPSA-N
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Compound 38
Molecular Weight:333.465
Molecular Formula:C20H31NO3
InChIKey:GPJAZEPZOKPXAG-NBVRZTHBSA-N
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Compound 39
Molecular Weight:250.357
Molecular Formula:C14H18O2S
InChIKey:CVAGTOGITKNWBR-UHFFFAOYSA-N
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Compound 41
Molecular Weight:368.532
Molecular Formula:C23H28O2S
InChIKey:LZGJLTPXPXZRTE-GHVJWSGMSA-N
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Compound 42
Molecular Weight:256.32
Molecular Formula:C15H12O2S
InChIKey:LCFRAXQOCAQFJR-UHFFFAOYSA-N
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Compound 43
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 44
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 60
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 45
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:NEEDEQSZOUAJMU-UHFFFAOYSA-N
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Compound 46
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:KEZJKJKIMQLHRG-QPJJXVBHSA-N
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Compound 47
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:VNUUMNNQQSAYCU-UHFFFAOYSA-N
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Compound 48
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:NVDRTKDQNXWZSY-UHFFFAOYSA-N
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Compound 50
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 51
Molecular Weight:81.0727
Molecular Formula:C4H3NO
InChIKey:KSMNKZULGQZFCH-UHFFFAOYSA-N
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Compound 52
Molecular Weight:139.823
Molecular Formula:C4H2ClMgNO
InChIKey:YFOLOXUJZVSOIL-UHFFFAOYSA-M
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Compound 53
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 54
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 55
Molecular Weight:165.1891
Molecular Formula:C9H11NO2
InChIKey:PEUXMZWYTBZBLE-UHFFFAOYSA-N
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Compound 56
Molecular Weight:95.0993
Molecular Formula:C5H5NO
InChIKey:ROQTYQQFZQHWAM-UHFFFAOYSA-N
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Compound 57
Molecular Weight:190.2814
Molecular Formula:C13H18O
InChIKey:PTDTXGFVGLTWFO-ZWNOBZJWSA-N
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Compound 58
Molecular Weight:240.624
Molecular Formula:C15H20MgO
InChIKey:QLPPMCLACCFBMW-XRZFDKQNSA-N
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Compound 59
Molecular Weight:186.2066
Molecular Formula:C12H10O2
InChIKey:KFQNNYAHLPGVMV-UHFFFAOYSA-N
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Compound 61
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 62
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:GKPOMITUDGXOSB-UHFFFAOYSA-N
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Compound 63
Molecular Weight:268.1352
Molecular Formula:C9H17IO
InChIKey:UMUCRWXLPNIGJY-CLFYSBASSA-N
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Compound 64
Molecular Weight:268.1352
Molecular Formula:C9H17IO
InChIKey:QZBAZIPHBSRAJZ-CLFYSBASSA-N
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Compound 65
Molecular Weight:210.3556
Molecular Formula:C14H26O
InChIKey:QDLGCVOFPFXYHL-UHFFFAOYSA-N
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Compound 66
Molecular Weight:226.3981
Molecular Formula:C15H30O
InChIKey:RRSMCUDIPHKCKK-YPKPFQOOSA-N
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Compound 67
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:YGEQBZUDPQQIFI-UHFFFAOYSA-N
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Compound 68
Molecular Weight:232.3612
Molecular Formula:C16H24O
InChIKey:LQCWIKWJSQJHNK-DTQAZKPQSA-N
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Compound 69
Molecular Weight:159.2276
Molecular Formula:C11H13N
InChIKey:ARDFJWBFPXYFMH-UHFFFAOYSA-N
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Compound 70
Molecular Weight:201.3074
Molecular Formula:C14H19N
InChIKey:QDSJAXHVWDZKFA-SDNWHVSQSA-N
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Compound 71
Molecular Weight:197.3171
Molecular Formula:C12H23NO
InChIKey:WKUAPSBJRDQIMK-UHFFFAOYSA-N
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Compound 73
Molecular Weight:213.398
Molecular Formula:C8H13BrMg
InChIKey:JJSNFIZXOTWTNW-RQCPZROWSA-M
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Compound 72
Molecular Weight:189.093
Molecular Formula:C8H13Br
InChIKey:IXLZYSSNEZDYMF-VOTSOKGWSA-N
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Compound 74
Molecular Weight:213.398
Molecular Formula:C8H13BrMg
InChIKey:HNRMGOSHDDXYAX-YUZCMTBUSA-M
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Compound 75
Molecular Weight:94.1543
Molecular Formula:C7H10
InChIKey:KYSZFXOVOHPNSF-UHFFFAOYSA-N
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Compound 77
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:AINMINDCBBSFAO-UHFFFAOYSA-N
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Compound 78
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 80
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 81
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:SNBCLPBUNNRABI-SNVBAGLBSA-N
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Compound 83
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:CNKAOWOWVMHPSR-UHFFFAOYSA-N
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Compound 85
Molecular Weight:249.263
Molecular Formula:C10H21BrSi
InChIKey:FERAFADVLWDANH-VQHVLOKHSA-N
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Compound 87
Molecular Weight:170.3672
Molecular Formula:C10H22Si
InChIKey:YMZOQVZPAXMCOJ-VHSXEESVSA-N
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Compound E-88
Molecular Weight:257.17
Molecular Formula:C12H25ClMgSi
InChIKey:WELUTQMJZQJVSG-OTBYXNOXSA-M
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Compound Z-88
Molecular Weight:257.17
Molecular Formula:C12H25ClMgSi
InChIKey:WELUTQMJZQJVSG-WSELPHFCSA-M
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Compound 92
Molecular Weight:257.4875
Molecular Formula:C14H31NOSi
InChIKey:RICMLCFXYVJGLK-UHFFFAOYSA-N
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Compound 93
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:GPAVHRUFYAKWQX-UHFFFAOYSA-N
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Compound 90
Molecular Weight:173.3281
Molecular Formula:C8H19NOSi
InChIKey:ZYVNUWZRVLMXJN-UHFFFAOYSA-N
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Compound 94
Molecular Weight:163.2917
Molecular Formula:C9H13NSi
InChIKey:UAMVROIJEVLNFM-UHFFFAOYSA-N
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Compound 96
Molecular Weight:219.398
Molecular Formula:C13H21NSi
InChIKey:UJRQJHNCGGKBJG-FMIVXFBMSA-N
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Compound 97
Molecular Weight:317.5841
Molecular Formula:C20H35NSi
InChIKey:QCOCLVLTHKBJSJ-UHFFFAOYSA-N
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Compound 98
Molecular Weight:198.3449
Molecular Formula:C13H26O
InChIKey:NRNIWZBNOSFROG-UHFFFAOYSA-N
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Compound 99
Molecular Weight:224.2976
Molecular Formula:C16H16O
InChIKey:MCIWONLOVGQSQX-UHFFFAOYSA-N
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Compound 102
Molecular Weight:266.3774
Molecular Formula:C19H22O
InChIKey:ROEFYOJWIRNESC-UHFFFAOYSA-N
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Compound 103
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:CTHUAOGQNZSMMC-UHFFFAOYSA-N
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Compound 104
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:MKUWVMRNQOOSAT-UHFFFAOYSA-N
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Compound 105
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:KSXVDBSINBXKGA-BQBZGAKWSA-N
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Compound 106
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:KSXVDBSINBXKGA-NKWVEPMBSA-N
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Compound 107
Molecular Weight:144.2868
Molecular Formula:C7H16OSi
InChIKey:DESHOKKWDVAXSP-AATRIKPKSA-N
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Compound 108
Molecular Weight:361.15
Molecular Formula:C16H34OSn
InChIKey:JDGHITRWXNGSKV-UHFFFAOYSA-N
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Compound 109
Molecular Weight:133.1903
Molecular Formula:C9H11N
InChIKey:RDAFNSMYPSHCBK-QPJJXVBHSA-N
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Compound 111
Molecular Weight:161.2435
Molecular Formula:C11H15N
InChIKey:SYUYXOYNRMMOGW-RMKNXTFCSA-N
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Compound 110
Molecular Weight:175.2701
Molecular Formula:C12H17N
InChIKey:BJSKHSLLSNATNR-UHFFFAOYSA-N
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Compound 112
Molecular Weight:203.3232
Molecular Formula:C14H21N
InChIKey:OSHBORLZNHTWCE-UHFFFAOYSA-N
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Compound 113
Molecular Weight:216.161
Molecular Formula:C14H9LiO2
InChIKey:UWTOJFABHBNFSP-UHFFFAOYSA-N
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Compound 114
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 115
Molecular Weight:151.1626
Molecular Formula:C8H9NO2
InChIKey:MRXDPIUTOBSQLY-QMMMGPOBSA-N
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Compound 116
Molecular Weight:83.0886
Molecular Formula:C4H5NO
InChIKey:LZJDCFUZEZQGQR-OWOJBTEDSA-N
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Compound 118
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 119
Molecular Weight:141.1677
Molecular Formula:C7H11NO2
InChIKey:MVYJXAGLEXAEGC-ONEGZZNKSA-N
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Compound 120
Molecular Weight:111.1418
Molecular Formula:C6H9NO
InChIKey:DRWFRCFENQRMFP-HNQUOIGGSA-N
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Compound 121
Molecular Weight:125.1683
Molecular Formula:C7H11NO
InChIKey:WBFIMIWECMSVGH-DUXPYHPUSA-N
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Compound 122
Molecular Weight:123.1525
Molecular Formula:C7H9NO
InChIKey:LKDIPHAFHPYCOL-UHFFFAOYSA-N
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Compound 123
Molecular Weight:137.179
Molecular Formula:C8H11NO
InChIKey:JUIDUZOWQWUDBQ-FNORWQNLSA-N
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Compound 125
Molecular Weight:206.995
Molecular Formula:C11H15ClMg
InChIKey:BHQLEYPGIDUKGH-UHFFFAOYSA-M
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Compound 124
Molecular Weight:121.1366
Molecular Formula:C7H7NO
InChIKey:HFBNSECTGDGKLE-UHFFFAOYSA-N
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Compound 126
Molecular Weight:299.4504
Molecular Formula:C20H29NO
InChIKey:PFYICDWEUODYHD-AQNXPRMDSA-N
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Compound 127
Molecular Weight:281.4351
Molecular Formula:C20H27N
InChIKey:KSODEYYYINEFHT-FXJNCMGBSA-N
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Compound 128
Molecular Weight:300.4351
Molecular Formula:C20H28O2
InChIKey:NFWKVWVWBFBAOV-GQXIWKRZSA-N
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Compound 129
Molecular Weight:170.2918
Molecular Formula:C11H22O
InChIKey:NAOMHUDQUVEWEF-UHFFFAOYSA-N
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Compound 130
Molecular Weight:184.3184
Molecular Formula:C12H24O
InChIKey:PVJNOPTVAARPJL-UHFFFAOYSA-N
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Compound 131
Molecular Weight:284.5526
Molecular Formula:C17H36OSi
InChIKey:JFDPXBDRYCMKJO-UHFFFAOYSA-N
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Compound 132
Molecular Weight:168.319
Molecular Formula:C12H24
InChIKey:LGTWOHHRJHHWCO-UHFFFAOYSA-N
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Compound 133
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:MKOSBHNWXFSHSW-DSYKOEDSSA-N
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Compound 134
Molecular Weight:484.657
Molecular Formula:C24H34Cl2Zr
InChIKey:ARRQFKMLKCYIMJ-XMEAZBQQSA-L
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Compound 135
Molecular Weight:133.1903
Molecular Formula:C9H11N
InChIKey:LQFLWKPCQITJIH-UHFFFAOYSA-N
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Compound 136
Molecular Weight:209.351
Molecular Formula:C12H19NS
InChIKey:XPHHVPBDHBELAR-LLVKDONJSA-N
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Compound 137
Molecular Weight:147.2169
Molecular Formula:C10H13N
InChIKey:WJYIMFNLIJXFMX-UHFFFAOYSA-N
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Compound 138
Molecular Weight:223.378
Molecular Formula:C13H21NS
InChIKey:BQINZAHTNVLAKH-GFCCVEGCSA-N
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Compound 139
Molecular Weight:275.3444
Molecular Formula:C19H17NO
InChIKey:QOBMAXCQZVIZGR-OYKVQYDMSA-N
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  1. 1 - 125