(R)-(+)-phenylmethyl 4-chloro-3-hydroxybutanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-(+)-phenylmethyl 4-chloro-3-hydroxybutanoate
• 英文别名: benzyl (3R)-4-chloro-3-hydroxybutanoate
• 化学式: C₁₁H₁₃ClO₃
• 分子量: 228.675
• InChiKey: AJGRCWAJLBXPIY-SNVBAGLBSA-N

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：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  benzyl 3-butenoate 在 间氯过氧苯甲酸 、 lithium chloride 、 copper dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 186.0h， 生成 (R)-(+)-phenylmethyl 4-chloro-3-hydroxybutanoate
  参考文献：
  名称：

  Lipase-catalyzed resolution of esters of 4-chloro-3-hydroxybutanoic acid: effects of the alkoxy group and solvent on the enantiomeric ratio

  摘要：

  Various lipases have been investigated for their potential use as catalysts for the resolution of esters of 4-chloro-3-hydroxybutanoic acid via transesterification in organic solvents. Rhizomucor miehei lipase was found to be the most efficient lipase, with the enantiomeric ratio (E) being dependent upon of the nature of the alkoxy group of the ester and the resolution medium. Higher E-values were obtained when transesterification was performed in benzene or carbon tetrachloride than was the case in hexane. In mixtures of benzene and hexane the trend in E-values followed a linear relationship. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00126-3

文献信息

• US4642290A
  申请人：——

  公开号：US4642290A

  公开（公告）日：1987-02-10
• US4710468A
  申请人：——

  公开号：US4710468A

  公开（公告）日：1987-12-01
• Lipase-catalyzed resolution of esters of 4-chloro-3-hydroxybutanoic acid: effects of the alkoxy group and solvent on the enantiomeric ratio
  作者：Bård Helge Hoff、Thorleif Anthonsen

  DOI：10.1016/s0957-4166(99)00126-3

  日期：1999.4

  Various lipases have been investigated for their potential use as catalysts for the resolution of esters of 4-chloro-3-hydroxybutanoic acid via transesterification in organic solvents. Rhizomucor miehei lipase was found to be the most efficient lipase, with the enantiomeric ratio (E) being dependent upon of the nature of the alkoxy group of the ester and the resolution medium. Higher E-values were obtained when transesterification was performed in benzene or carbon tetrachloride than was the case in hexane. In mixtures of benzene and hexane the trend in E-values followed a linear relationship. (C) 1999 Elsevier Science Ltd. All rights reserved.