ethyl (3S)-4-hydroxy-3-phenylbutanoate | 1431854-78-2

• 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: ethyl (3S)-4-hydroxy-3-phenylbutanoate
• CAS: 1431854-78-2
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: CMAUOBGXNGYKIG-LLVKDONJSA-N

物化性质

• 沸点：
  327.2±30.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (3S)-4-hydroxy-3-phenylbutanoate 在 盐酸 、 4-二甲氨基吡啶 、 sodium azide 、 18-冠醚-6 、 palladium on activated charcoal 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 112.0h， 生成 (3S)-4-氨基-3-苯基丁酸盐酸盐
  参考文献：
  名称：

  Studies on the chemoenzymatic synthesis of 3-phenyl-GABA and 4-phenyl-pyrrolid-2-one: the influence of donor of the alkoxy group on enantioselective esterification

  摘要：

  A new chemoenzymatic method for the synthesis of enantiomerically pure 3-phenyl-gamma-aminobutyric acid 1 and 4-phenyl-pyrrolid-2-one 9 based on the enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid 2 is described herein. Enzymatic resolution of the racemic substrate provided products with good enantiselectivity upon esterification. In these reactions, a new class of alkoxy group donor-orthoesters, acetals and ketals were used. The best results of the enzymatic kinetic resolution were obtained for triethyl orthoacetate in toluene solvent. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.016
• 作为产物：
  描述：

  3-phenylpent-4-enoic acid 在 Wheat Germ lipase 、 sodium cyanoborohydride 、 臭氧 作用下， 以 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 24.83h， 生成 ethyl (3S)-4-hydroxy-3-phenylbutanoate
  参考文献：
  名称：

  Studies on the chemoenzymatic synthesis of 3-phenyl-GABA and 4-phenyl-pyrrolid-2-one: the influence of donor of the alkoxy group on enantioselective esterification

  摘要：

  A new chemoenzymatic method for the synthesis of enantiomerically pure 3-phenyl-gamma-aminobutyric acid 1 and 4-phenyl-pyrrolid-2-one 9 based on the enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid 2 is described herein. Enzymatic resolution of the racemic substrate provided products with good enantiselectivity upon esterification. In these reactions, a new class of alkoxy group donor-orthoesters, acetals and ketals were used. The best results of the enzymatic kinetic resolution were obtained for triethyl orthoacetate in toluene solvent. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.016