6-hexanoyloxy-3,5,5-trimethylcyclohex-2-enone

• 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: 6-hexanoyloxy-3,5,5-trimethylcyclohex-2-enone
• 英文别名: (4,6,6-Trimethyl-2-oxocyclohex-3-en-1-yl) hexanoate；(4,6,6-trimethyl-2-oxocyclohex-3-en-1-yl) hexanoate
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: LUVIWJRSMDTSCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异佛尔酮 、 己酸 在 potassium permanganate 、 己酸酐 作用下， 以 苯 为溶剂， 反应 0.5h， 以81%的产率得到6-hexanoyloxy-3,5,5-trimethylcyclohex-2-enone
  参考文献：
  名称：

  Acyloxylation of Cyclic Enones: Synthesis of Densely Oxygenated Guaianolides

  摘要：

  The alpha'-acyloxylation of cyclic enones with linear carboxylic acids is described. The reaction is promoted by KMnO4 in the presence of a carboxylic acid and its corresponding carboxylic anhydride. The optimization of the reaction has been carried out using the statistical methodology known as design of experiments. The optimized reaction conditions have been evaluated in terms of substrate scope and compatibility with different functional groups. The methodology has been applied to the synthesis of densely oxygenated guaianes and guaianolides.

  DOI：

  10.1021/jo500915r

文献信息

• Acyloxylation of Cyclic Enones: Synthesis of Densely Oxygenated Guaianolides
  作者：Rubén Marín-Barrios、Ana Leticia García-Cabeza、F. Javier Moreno-Dorado、Francisco M. Guerra、Guillermo M. Massanet

  DOI：10.1021/jo500915r

  日期：2014.7.18

  The alpha'-acyloxylation of cyclic enones with linear carboxylic acids is described. The reaction is promoted by KMnO4 in the presence of a carboxylic acid and its corresponding carboxylic anhydride. The optimization of the reaction has been carried out using the statistical methodology known as design of experiments. The optimized reaction conditions have been evaluated in terms of substrate scope and compatibility with different functional groups. The methodology has been applied to the synthesis of densely oxygenated guaianes and guaianolides.