(R)-3-hydroxy-3,7-dimethyl-2-oxo-6-octenyl 4-bromobenzoate | 1609197-53-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (R)-3-hydroxy-3,7-dimethyl-2-oxo-6-octenyl 4-bromobenzoate
• CAS: 1609197-53-6
• 化学式: C₁₇H₂₁BrO₄
• 分子量: 369.255
• InChiKey: HWXBJVLPPOPVSH-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxy-3,7-dimethyl-2-oxo-6-octenyl 4-bromobenzoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以81%的产率得到(R)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one
  参考文献：
  名称：

  Catalytic asymmetric synthesis of the Colorado potato beetle pheromone and its enantiomer

  摘要：

  An efficient catalytic asymmetric synthesis of the CPB pheromone [(S)-1,3-dihydroxy-3,7-dimethy1-6-octen-2-one] and its enantiomer was accomplished with 99% ee and in gram quantities from geraniol. The key steps in this procedure involve Sharpless asymmetric epoxidation and recrystallization of the 4-bromobenzoate from the CPB pheromone to improve its enantiomeric purity. Furthermore, the absolute configuration of the CPB pheromone enantiomer was confirmed as (R) for the first time by the X-ray crystallographic structure of its benzoate. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.018
• 作为产物：
  描述：

  4-溴苯甲酰氯 、 (R)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到(R)-3-hydroxy-3,7-dimethyl-2-oxo-6-octenyl 4-bromobenzoate
  参考文献：
  名称：

  Catalytic asymmetric synthesis of the Colorado potato beetle pheromone and its enantiomer

  摘要：

  An efficient catalytic asymmetric synthesis of the CPB pheromone [(S)-1,3-dihydroxy-3,7-dimethy1-6-octen-2-one] and its enantiomer was accomplished with 99% ee and in gram quantities from geraniol. The key steps in this procedure involve Sharpless asymmetric epoxidation and recrystallization of the 4-bromobenzoate from the CPB pheromone to improve its enantiomeric purity. Furthermore, the absolute configuration of the CPB pheromone enantiomer was confirmed as (R) for the first time by the X-ray crystallographic structure of its benzoate. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.12.018