Succinic acid mono-((S)-2-isopropenyl-5-methyl-hex-4-enyl) ester | 881920-45-2

• 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
• 英文名称: Succinic acid mono-((S)-2-isopropenyl-5-methyl-hex-4-enyl) ester
• 英文别名: 4-[(2S)-5-methyl-2-prop-1-en-2-ylhex-4-enoxy]-4-oxobutanoic acid
• CAS: 881920-45-2
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: WIFAXJZHWSAHGM-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  Succinic acid mono-((S)-2-isopropenyl-5-methyl-hex-4-enyl) ester 在 氢氧化钾 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.0h， 生成 (S)-lavandulol
  参考文献：
  名称：

  A convenient resolution of racemic lavandulol through lipase-catalyzed acylation with succinic anhydride: simple preparation of enantiomerically pure (R)-lavandulol

  摘要：

  (R)- and (S)-lavandulol and their esters are important compounds in perfumery and have recently become significant in pheromone research. (R)-Lavandulol and its esters, as well as the esters of (S)-lavandulol have been identified as sex and aggregation pheromones in two mealybugs, in thrips and in weevils. We report a convenient resolution of racemic lavandulol through lipase-catalyzed acylation with succinic anhydride. This method does not require tedious chromatographic separation and is particularly suitable for the preparation of enantiomerically pure (R)-lavandulol with 98% ee in one resolution cycle. The (S)-lavandulol with 90% ee can be obtained by a second resolution cycle. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.021
• 作为产物：
  描述：

  丁二酸酐 、 拉凡醇; 5-甲基-2-(1-甲基乙烯基)-4-己烯-1-醇 在 hog pancreas lipase 作用下， 以 乙醚 为溶剂， 反应 48.0h， 生成 Succinic acid mono-((S)-2-isopropenyl-5-methyl-hex-4-enyl) ester 、 Succinic acid mono-((R)-2-isopropenyl-5-methyl-hex-4-enyl) ester 、 熏衣草醇
  参考文献：
  名称：

  A convenient resolution of racemic lavandulol through lipase-catalyzed acylation with succinic anhydride: simple preparation of enantiomerically pure (R)-lavandulol

  摘要：

  (R)- and (S)-lavandulol and their esters are important compounds in perfumery and have recently become significant in pheromone research. (R)-Lavandulol and its esters, as well as the esters of (S)-lavandulol have been identified as sex and aggregation pheromones in two mealybugs, in thrips and in weevils. We report a convenient resolution of racemic lavandulol through lipase-catalyzed acylation with succinic anhydride. This method does not require tedious chromatographic separation and is particularly suitable for the preparation of enantiomerically pure (R)-lavandulol with 98% ee in one resolution cycle. The (S)-lavandulol with 90% ee can be obtained by a second resolution cycle. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.021