(环己基)(香叶基)乙酸 | 23266-76-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (环己基)(香叶基)乙酸
• 英文名称: (E)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid
• 英文别名: (cyclohexyl)(geranyl)acetic acid；(+/-)-2.6-dimethyl-9-cyclohexyl-decadien-(2.6t)-oic acid-(10)；(+/-)-2.6-Dimethyl-9-cyclohexyl-decadien-(2.6t)-saeure-(10)；2-Cylohexyl-2-geranyl-essigsaeure；Cygerol；(4E)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid
• CAS: 23266-76-4
• 化学式: C₁₈H₃₀O₂
• 分子量: 278.435
• InChiKey: WIHSFNRKGXNWNK-NTCAYCPXSA-N

物化性质

• 沸点：
  413.3±24.0 °C(Predicted)
• 密度：
  0.964±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (环己基)(香叶基)乙酸 在 乙醇 、 硫酸 作用下， 生成 ethyl (E)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoate
  参考文献：
  名称：

  Leder-Packendorff, Doklady Akademii Nauk SSSR, 1941, vol. 31, p. 757,759

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (E)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoate 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 25.0h， 以95%的产率得到(环己基)(香叶基)乙酸
  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

文献信息

• Kinetic resolution of racemic (cyclohexyl)(geranyl)acetic acid
  作者：Sergei G. Zlotin、Galina V. Kryshtal、Galina M. Zhdankina、Anna A. Sukhanova、Alexander S. Kucherenko、Boris B. Smirnov、Vladimir A. Tartakovsky

  DOI：10.1016/j.mencom.2014.09.002

  日期：2014.9

  A kinetic resolution of racemic (cyclohexyl)(geranyl)acetic acid, the active ingredient of wound-curing medication Cygerol, to (S)- and (R)-enantiomers was achieved by diastereoselective esterification with (S)- or (R)-BINOL.
• US4025539A
  申请人：——

  公开号：US4025539A

  公开（公告）日：1977-05-24
• 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.
• Leder-Packendorff, Doklady Akademii Nauk SSSR, 1941, vol. 31, p. 757,759
  作者：Leder-Packendorff

  DOI：——

  日期：——