(R)-4-oxo-3,5,5-trimethyl-2-cyclohexenyl chloroacetate | 254963-55-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-4-oxo-3,5,5-trimethyl-2-cyclohexenyl chloroacetate
• 英文别名: [(1R)-3,5,5-trimethyl-4-oxocyclohex-2-en-1-yl] 2-chloroacetate
• CAS: 254963-55-8
• 化学式: C₁₁H₁₅ClO₃
• 分子量: 230.691
• InChiKey: UMYHTSRDURNVOC-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-oxo-3,5,5-trimethyl-2-cyclohexenyl chloroacetate 在 甲醇 、 potassium carbonate 作用下， 反应 4.0h， 生成 (+)-(R)-4-Hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one
  参考文献：
  名称：

  Hydrolase-catalyzed preparation of (R)- and (S)-4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-ones (phorenols), the key synthetic intermediates for abscisic acid

  摘要：

  Preparation of both the enantiomers of 4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one (phorenol), which are versatile synthetic intermediates for abscisic acid and carotenoids, was achieved by hydrolase-catalyzed hydrolysis of the corresponding chloroacetate. The hydrolysis with esterase SNSM-87 (Nagase) enriched the (S)-ester, while lipase P (Amano) afforded the (R)-ester. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00391-2
• 作为产物：
  描述：

  4-羟基-2,6,6-三甲基环己-2-烯-1-酮 在 吡啶 、 phosphate buffer 、 lipase P (Amano) 作用下， 以 乙醚 、 异丙醚 为溶剂， 反应 53.0h， 生成 (R)-4-oxo-3,5,5-trimethyl-2-cyclohexenyl chloroacetate
  参考文献：
  名称：

  Hydrolase-catalyzed preparation of (R)- and (S)-4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-ones (phorenols), the key synthetic intermediates for abscisic acid

  摘要：

  Preparation of both the enantiomers of 4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one (phorenol), which are versatile synthetic intermediates for abscisic acid and carotenoids, was achieved by hydrolase-catalyzed hydrolysis of the corresponding chloroacetate. The hydrolysis with esterase SNSM-87 (Nagase) enriched the (S)-ester, while lipase P (Amano) afforded the (R)-ester. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00391-2