Standard Article

Preparation and Reactivity of Magnesium Enolates

Organomagnesium Compounds (2008)

  1. Claude Grison

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0410

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Grison, C. 2009. Preparation and Reactivity of Magnesium Enolates. Patai's Chemistry of Functional Groups. .

Author Information

  1. UMR CNRS-Université de Montpellier 2 5032, ENSCM, Montpellier, France

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    Introduction
  • 2
    Preparation of Magnesium Enolates
  • 3
    Reactivity of Enolates

Keywords:

  • enolate anions and carbon–carbon bond formation;
  • magnesium enolate preparation;
  • permutational metal/metal salt interconversions;
  • enolization reactions mediated by magnesium amides;
  • magnesium amides and enantioselective deprotonation processes;
  • magnesium enolate reactivity;
  • magnesium ketone enolate and electrophile reaction;
  • magnesium-halide-mediated aldol reactions

Featured Compounds

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  1. 1 - 121
Compound 2
Molecular Weight:255.435
Molecular Formula:C10H15BrMgO
InChIKey:NUWBZLOWXZJJJG-CJYAGVAKSA-L
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Compound 1
Molecular Weight:231.13
Molecular Formula:C10H15BrO
InChIKey:NJQADTYRAYFBJN-IROMYEEYSA-N
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Compound 4
Molecular Weight:353.536
Molecular Formula:C18H17BrMgO
InChIKey:YIEXCDLQRVRDLM-UHFFFAOYSA-L
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Compound 3
Molecular Weight:329.231
Molecular Formula:C18H17BrO
InChIKey:MUDHJVKKARQCJX-UHFFFAOYSA-N
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Compound 5
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 7
Molecular Weight:205.092
Molecular Formula:C8H13BrO
InChIKey:PABTVPFOBJQABJ-UHFFFAOYSA-N
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Compound 8
Molecular Weight:229.397
Molecular Formula:C8H13BrMgO
InChIKey:ZQIAJERKCOVHJI-UHFFFAOYSA-L
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Compound 9
Molecular Weight:583.016
Molecular Formula:C22H46Br2Mg2O4
InChIKey:PHYMPAYSRJWUGC-YDKZHPKBSA-J
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Compound 11
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 12
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:OGCGGWYLHSJRFY-UHFFFAOYSA-N
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Compound 13
Molecular Weight:238.3657
Molecular Formula:C15H26O2
InChIKey:ONECILGFBWGHTE-UHFFFAOYSA-N
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Compound 14
Molecular Weight:222.3663
Molecular Formula:C15H26O
InChIKey:QZFSNJAQFWEXEA-MDZDMXLPSA-N
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Compound 15
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 15a
Molecular Weight:206.667
Molecular Formula:C9H15ClO3
InChIKey:VLRHXVQJEBQXPD-UHFFFAOYSA-N
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Compound 15b
Molecular Weight:192.64
Molecular Formula:C8H13ClO3
InChIKey:BSTNWWVFDJXLKY-UHFFFAOYSA-N
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Compound 15c
Molecular Weight:268.736
Molecular Formula:C14H17ClO3
InChIKey:UHACANJNZVDHDG-UHFFFAOYSA-N
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Compound 15d
Molecular Weight:400.851
Molecular Formula:C19H25ClO7
InChIKey:MDHKTIGXAOQLEM-OTCUZQLFSA-N
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Compound 15e
Molecular Weight:368.807
Molecular Formula:C15H25ClO8
InChIKey:CZIPAEPRBWIFIF-GAOBNZSZSA-N
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Compound 15f
Molecular Weight:497.095
Molecular Formula:C22H41ClO8Si
InChIKey:BGPTVUUCYNUVMH-DYLZQPSASA-N
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Compound 17a
Molecular Weight:294.37
Molecular Formula:C7H11IMgO3
InChIKey:HHAULCRXNNOGHD-SLNOCBGISA-L
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Compound 18
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 18a
Molecular Weight:172.2215
Molecular Formula:C9H16O3
InChIKey:SXZJHJWZOCCJJJ-UHFFFAOYSA-N
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Compound 18b
Molecular Weight:158.195
Molecular Formula:C8H14O3
InChIKey:PMHFVUJFYKWCDE-UHFFFAOYSA-N
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Compound 18c
Molecular Weight:234.2909
Molecular Formula:C14H18O3
InChIKey:GRMOOOBHVDXPFV-UHFFFAOYSA-N
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Compound 18d
Molecular Weight:366.4055
Molecular Formula:C19H26O7
InChIKey:XHCXXQKEOCYTOO-DFEOGRTESA-N
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Compound 18-d1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 18-d2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 18e
Molecular Weight:334.3621
Molecular Formula:C15H26O8
InChIKey:AJTXJMYDKIFLEF-KDBYPZKRSA-N
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Compound 18f
Molecular Weight:462.6496
Molecular Formula:C22H42O8Si
InChIKey:HVFXFEUOLVGSCU-NCXUSEDFSA-N
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Compound 20
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 19
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 21
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 58
Molecular Weight:254.345
Molecular Formula:C13H18O3S
InChIKey:ATKQQTNXMNHRCW-QGZVFWFLSA-N
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Compound 22
Molecular Weight:315.605
Molecular Formula:C12H23BrMgOSi
InChIKey:TWFLIXKYIULQCV-UHFFFAOYSA-L
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Compound 23
Molecular Weight:132.1625
Molecular Formula:C8H8N2
InChIKey:SHIBMGQAICRHTE-UHFFFAOYSA-N
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Compound 46
Molecular Weight:224.669
Molecular Formula:C12H28MgN2
InChIKey:XDBOBNVQEBSKFO-UHFFFAOYSA-N
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Compound 24
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 25
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:1294.321
Molecular Formula:C78H110Mg2N4Na2O6
InChIKey:BJEHCMZVZUEQAH-UHFFFAOYSA-H
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Compound 31
Molecular Weight:931.533
Molecular Formula:C55H80MgN4Na2O4
InChIKey:AAEMQYCCAKHOMQ-UHFFFAOYSA-J
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Compound 32
Molecular Weight:1086.109
Molecular Formula:C64H102Mg2N4Na2O4
InChIKey:IWBIJOCUVVNXNM-UHFFFAOYSA-J
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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 35
Molecular Weight:168.1467
Molecular Formula:C8H8O4
InChIKey:PKLPQOJFHFGVBS-UHFFFAOYSA-N
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Compound 36
Molecular Weight:158.1519
Molecular Formula:C7H10O4
InChIKey:JUKCTOHWTHYRPF-UHFFFAOYSA-N
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Compound 88
Molecular Weight:233.2631
Molecular Formula:C13H15NO3
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 90
Molecular Weight:265.394
Molecular Formula:C13H15NOS2
InChIKey:ZSVSIHWUEYQGRS-NSHDSACASA-N
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Compound 91
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 39
Molecular Weight:204.391
Molecular Formula:C6H14BrMgN
InChIKey:UODMSBYDFUPQHC-UHFFFAOYSA-M
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Compound 40
Molecular Weight:159.94
Molecular Formula:C6H14ClMgN
InChIKey:RMHOGFJEHWOPLT-UHFFFAOYSA-M
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Compound 43
Molecular Weight:244.455
Molecular Formula:C9H18BrMgN
InChIKey:JFBCAZSKGDCEOQ-UHFFFAOYSA-M
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Compound 44
Molecular Weight:176.338
Molecular Formula:C4H10BrMgN
InChIKey:HEVSIKNIWJEAAA-UHFFFAOYSA-M
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Compound 45
Molecular Weight:244.455
Molecular Formula:C9H18BrMgN
InChIKey:GJLKEMXUFZIYRN-UHFFFAOYSA-M
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Compound 47
Molecular Weight:345.075
Molecular Formula:C12H36MgN2Si4
InChIKey:WYPTZCBYSQFOQS-UHFFFAOYSA-N
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Compound 48
Molecular Weight:192.498
Molecular Formula:C8H12MgN2O2
InChIKey:FSXYVRLAPVGHOC-UHFFFAOYSA-L
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Compound 60
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 41
Molecular Weight:264.594
Molecular Formula:C6H18BrMgNSi2
InChIKey:HFIJANVQJMJRRW-UHFFFAOYSA-M
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Compound 42
Molecular Weight:284.519
Molecular Formula:C12H22BrMgN
InChIKey:GDBLAHBMCQVCRU-UHFFFAOYSA-M
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Compound 49
Molecular Weight:662.7123
Molecular Formula:C30H51IO6Si
InChIKey:SAOFEYXQAMFBTK-RUMFETKXSA-N
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Compound 51
Molecular Weight:704.9008
Molecular Formula:C34H61O11PSi
InChIKey:UGWKWPHGEXSIOC-LOYHVIPDSA-N
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Compound 52
Molecular Weight:651.0766
Molecular Formula:C36H66O6Si2
InChIKey:FKQAUWZQTHJSRU-ROJLCIKYSA-N
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Compound 56
Molecular Weight:291.54
Molecular Formula:C9H19BrMgO2Si
InChIKey:AFLCWDMEGXSAPX-OTMFCZTRSA-L
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Compound 55
Molecular Weight:178.2277
Molecular Formula:C11H14O2
InChIKey:XYUPRHVYEKOWCD-JTQLQIEISA-N
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Compound 57
Molecular Weight:252.3062
Molecular Formula:C14H20O4
InChIKey:XEQGKKHKACMSKL-NTZNESFSSA-N
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Compound 59
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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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:251.2784
Molecular Formula:C13H17NO4
InChIKey:AUQYLAKMWJNZTO-LRCZMLTDSA-N
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Compound 63
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 64
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 65
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 66
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 65d
Molecular Weight:502.4918
Molecular Formula:C23H35O10P
InChIKey:ZKEZEFRIKHQRRZ-KMIKSKCJSA-N
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Compound 65e
Molecular Weight:470.4484
Molecular Formula:C19H35O11P
InChIKey:JZBOBGJLWXIRLG-GGXOKAFJSA-N
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Compound 63a
Molecular Weight:216.2741
Molecular Formula:C11H20O4
InChIKey:KHLGVAMVYRWCBM-POHAHGRESA-N
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Compound 63b
Molecular Weight:202.2475
Molecular Formula:C10H18O4
InChIKey:HKBGAGCKZGCFNH-TWGQIWQCSA-N
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Compound 63c
Molecular Weight:278.3435
Molecular Formula:C16H22O4
InChIKey:WRWJOYSAGYBKSN-GDNBJRDFSA-N
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Compound 63d
Molecular Weight:410.4581
Molecular Formula:C21H30O8
InChIKey:YOEBCIZXWGGKLW-POHVZQNKSA-N
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Compound 63e
Molecular Weight:378.4147
Molecular Formula:C17H30O9
InChIKey:QAVLHJUULCHHCQ-QIIZOYRASA-N
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Compound 64a
Molecular Weight:186.2481
Molecular Formula:C10H18O3
InChIKey:VUHPFSQFFWVAKJ-TWGQIWQCSA-N
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Compound 64b
Molecular Weight:172.2215
Molecular Formula:C9H16O3
InChIKey:WYGDIWBZAUNAGA-VURMDHGXSA-N
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Compound 64c
Molecular Weight:248.3175
Molecular Formula:C15H20O3
InChIKey:IVYMPKPZEWRJSN-UVTDQMKNSA-N
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Compound 64d
Molecular Weight:380.4321
Molecular Formula:C20H28O7
InChIKey:WGZBEFSGXUCBOW-JWXRYPRRSA-N
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Compound 64e
Molecular Weight:348.3887
Molecular Formula:C16H28O8
InChIKey:BXLPRUXBTQYPDR-NXBIRAQUSA-N
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Compound 65a
Molecular Weight:308.3078
Molecular Formula:C13H25O6P
InChIKey:CGVHQIYBJOBKKG-FMIVXFBMSA-N
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Compound 65b
Molecular Weight:294.2812
Molecular Formula:C12H23O6P
InChIKey:HKZIKTPNOFMWRP-LUAWRHEFSA-N
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Compound 65c
Molecular Weight:370.3771
Molecular Formula:C18H27O6P
InChIKey:IMMXINNCRLVDHL-GHRIWEEISA-N
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Compound 66a
Molecular Weight:244.4027
Molecular Formula:C12H24O3Si
InChIKey:CKOCPAPZZYEFDU-FLIBITNWSA-N
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Compound 66b
Molecular Weight:230.3761
Molecular Formula:C11H22O3Si
InChIKey:OSIRUPDBYHSEPY-NTMALXAHSA-N
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Compound 66c
Molecular Weight:306.472
Molecular Formula:C17H26O3Si
InChIKey:DDYWPNRAFNTMMW-VBKFSLOCSA-N
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Compound 66d
Molecular Weight:438.5867
Molecular Formula:C22H34O7Si
InChIKey:YHLWTUJBZFNQOC-POUMUBMISA-N
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Compound 66e
Molecular Weight:406.5433
Molecular Formula:C18H34O8Si
InChIKey:KXVICGWMGZIUPB-RXCZOSDSSA-N
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Compound 67
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 67a
Molecular Weight:216.2741
Molecular Formula:C11H20O4
InChIKey:RHTRXWZOFFEDIA-UHFFFAOYSA-N
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Compound 67c
Molecular Weight:278.3435
Molecular Formula:C16H22O4
InChIKey:XQDWBUOKMXBXNN-UHFFFAOYSA-N
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Compound 70
Molecular Weight:408.4407
Molecular Formula:C18H32O10
InChIKey:HVOIPFDHVQNLJB-BIZDNLSCSA-N
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Compound 69
Molecular Weight:374.426
Molecular Formula:C18H30O8
InChIKey:UAQCBQBCXMFCCL-YRWACRFQSA-N
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Compound 71
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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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:142.1956
Molecular Formula:C8H14O2
InChIKey:CRVBWHZZWOZRCY-UHFFFAOYSA-N
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Compound 74
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:AVXVDNJFGZNVAB-UHFFFAOYSA-N
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Compound 75
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:BDINBSUUIUWFNH-UHFFFAOYSA-N
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Compound 76
Molecular Weight:200.2316
Molecular Formula:C10H16O4
InChIKey:XMLTUUBNCIWHII-UHFFFAOYSA-N
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Compound 77
Molecular Weight:285.597
Molecular Formula:C12H22MgO6
InChIKey:BYTRKEJSDZTNFE-LGSAIMRHSA-M
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Compound 78
Molecular Weight:286.604
Molecular Formula:C12H22MgO6
InChIKey:LFXFHDATEXKATQ-UHFFFAOYSA-M
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Compound 79
Molecular Weight:336.2934
Molecular Formula:C16H16O8
InChIKey:OONPFPVHZWYFAZ-VOFQGDAYSA-N
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Compound 80
Molecular Weight:336.2934
Molecular Formula:C16H16O8
InChIKey:XVNGRHFFEFIIDE-OOFLMXFCSA-N
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Compound 81
Molecular Weight:525.074
Molecular Formula:C28H41ClO7
InChIKey:RHGMHWSMSRVZDT-DUNUWKEFSA-N
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Compound 82
Molecular Weight:648.7808
Molecular Formula:C35H52O11
InChIKey:SEQOWZXDESLLEL-JALVNXOESA-N
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Compound 83
Molecular Weight:650.7967
Molecular Formula:C35H54O11
InChIKey:AUZDOVGITPOSIU-QWLOQUMFSA-N
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Compound 84
Molecular Weight:468.6664
Molecular Formula:C27H48O6
InChIKey:DIPHJTHZUWDJIK-DQPYNAHXSA-N
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Compound 85
Molecular Weight:355.046
Molecular Formula:C9H9Br2NO2S
InChIKey:KHPFKNYSDZUEFH-MRVPVSSYSA-N
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Compound 86
Molecular Weight:320.203
Molecular Formula:C11H14BrNO3S
InChIKey:BAQSZGWIDRIXEZ-PFZYVWIYSA-N
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Compound 92
Molecular Weight:478.617
Molecular Formula:C20H24BrMgNO6
InChIKey:KLLAVSNCJHLHCV-OBEFCDIASA-L
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Compound 93
Molecular Weight:510.748
Molecular Formula:C20H24BrMgNO4S2
InChIKey:HRICDBGXDMGZPU-OBEFCDIASA-L
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Compound 95
Molecular Weight:159.2261
Molecular Formula:C8H17NO2
InChIKey:UEXXWHOBPJEQJJ-SSDOTTSWSA-N
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Compound 94
Molecular Weight:175.1824
Molecular Formula:C7H13NO4
InChIKey:WLTCKEHCTUYJGI-UHFFFAOYSA-N
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Compound 96
Molecular Weight:254.3254
Molecular Formula:C13H22N2O3
InChIKey:SEFOYIMQJDMNJT-VUWPPUDQSA-N
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  1. 1 - 121