γ-erucalactone | 16317-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: γ-erucalactone
• 英文别名: 5-octadecyl-dihydro-furan-2-one；5-Octadecyl-dihydro-furan-2-on；delta-Docosanolactone；5-octadecyloxolan-2-one
• CAS: 16317-09-2
• 化学式: C₂₂H₄₂O₂
• 分子量: 338.574
• InChiKey: QYFVOJZBVYWOPY-UHFFFAOYSA-N

物化性质

• 沸点：
  424.6±13.0 °C(Predicted)
• 密度：
  0.895±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  24
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  芥酸 在 [CholineCl][ZnCl₂]₃ 作用下， 反应 4.0h， 以42%的产率得到γ-erucalactone
  参考文献：
  名称：

  Tandem isomerization–lactonization of olefinic fatty acids using the Lewis acidic ionic liquid, choline chloride·2ZnCl2

  摘要：

  The tandem isomerization-lactonization of unsaturated fatty acids to their corresponding gamma-lactones was carried out for the first time in the presence of a Lewis acidic ionic liquid, choline chloride center dot 2ZnCl(2). The ionic liquid initially catalyzes the stepwise migration of the double bond along the carbon chain toward the carboxyl group at the Delta 4 position, which subsequently undergoes lactonization resulting in the formation of gamma-lactones. This one step process allows the formation of gamma-lactone in good yield with little or no formation of delta-lactones. The studied ionic liquid plays the dual role of solvent as well as catalyst. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.112

文献信息

• Shukow; Schestakow, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1908, vol. 40, p. 836
  作者：Shukow、Schestakow

  DOI：——

  日期：——
• Tandem isomerization–lactonization of olefinic fatty acids using the Lewis acidic ionic liquid, choline chloride·2ZnCl2
  作者：Shivaraju Akula、Pandari Phani Kumar、Rachapudi B.N. Prasad、Sanjit Kanjilal

  DOI：10.1016/j.tetlet.2012.04.112

  日期：2012.7

  The tandem isomerization-lactonization of unsaturated fatty acids to their corresponding gamma-lactones was carried out for the first time in the presence of a Lewis acidic ionic liquid, choline chloride center dot 2ZnCl(2). The ionic liquid initially catalyzes the stepwise migration of the double bond along the carbon chain toward the carboxyl group at the Delta 4 position, which subsequently undergoes lactonization resulting in the formation of gamma-lactones. This one step process allows the formation of gamma-lactone in good yield with little or no formation of delta-lactones. The studied ionic liquid plays the dual role of solvent as well as catalyst. (C) 2012 Elsevier Ltd. All rights reserved.