2-Cyclohexyl-succinic acid 1-ethyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Cyclohexyl-succinic acid 1-ethyl ester
• 英文别名: 3-Cyclohexyl-4-ethoxy-4-oxobutanoic acid
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: GVZQEMPGULANNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Cyclohexyl-succinic acid 1-ethyl ester 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-cyclohexyl-1,4-butanediol
  参考文献：
  名称：

  Synthesis and stereochemical assignment of geraniol- and nerol-derived Cygerol enantiomers

  摘要：

  The enantiomers (up to 99% ee) of both geraniol- and nerol-derived 2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid, the active ingredient of the wound healing medication Cygerol, were prepared via a low-temperature alkylation, basic hydrolysis, derivatization with (S)-4-benzyloxazolidin-2-one and chromatographic separation steps. The absolute configuration of stereocenters in the antipodes having an (E)- or (Z)-geometry of the internal double bond was determined based on characteristic H-1 NMR signals of the corresponding (S)-4-benzyloxazolidin-2-one-derived imides and on conversion to the known diethyl (S)-2-cyclohexylsuccinate and (S)-2-cyclohexylbutane-1,4-diol with reported specific rotations. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.10.024
• 作为产物：
  描述：

  丁二酸二乙酯 在 palladium on activated charcoal 氢气 、 sodium tert-pentoxide 作用下， 以 乙酸乙酯 、 苯 为溶剂， 生成 2-Cyclohexyl-succinic acid 1-ethyl ester
  参考文献：
  名称：

  Blanc,J.; Gastambide,B., Bulletin de la Societe Chimique de France, 1962, p. 2055 - 2064

  摘要：

  DOI：

文献信息

• US4542142A
  申请人：——

  公开号：US4542142A

  公开（公告）日：1985-09-17
• Synthesis and stereochemical assignment of geraniol- and nerol-derived Cygerol enantiomers
  作者：Anna A. Sukhanova、Ilya A. Puchkin、Andrei A. Vasil'ev、Sergei G. Zlotin

  DOI：10.1016/j.tetasy.2017.10.024

  日期：2017.12

  The enantiomers (up to 99% ee) of both geraniol- and nerol-derived 2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid, the active ingredient of the wound healing medication Cygerol, were prepared via a low-temperature alkylation, basic hydrolysis, derivatization with (S)-4-benzyloxazolidin-2-one and chromatographic separation steps. The absolute configuration of stereocenters in the antipodes having an (E)- or (Z)-geometry of the internal double bond was determined based on characteristic H-1 NMR signals of the corresponding (S)-4-benzyloxazolidin-2-one-derived imides and on conversion to the known diethyl (S)-2-cyclohexylsuccinate and (S)-2-cyclohexylbutane-1,4-diol with reported specific rotations. (C) 2017 Elsevier Ltd. All rights reserved.
• Blanc,J.; Gastambide,B., Bulletin de la Societe Chimique de France, 1962, p. 2055 - 2064
  作者：Blanc,J.、Gastambide,B.

  DOI：——

  日期：——