4-(4-Chloro-phenyl)-2-hydroxy-butyric acid ethyl ester | 214336-42-2

• 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: 4-(4-Chloro-phenyl)-2-hydroxy-butyric acid ethyl ester
• 英文别名: Ethyl 4-(4-chlorophenyl)-2-hydroxybutanoate
• CAS: 214336-42-2
• 化学式: C₁₂H₁₅ClO₃
• 分子量: 242.702
• InChiKey: CYSPYMLVCLECRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 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：

  4-(4-Chloro-phenyl)-2-hydroxy-butyric acid ethyl ester 在 Candida parapsilosis ATCC 7330 cells 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 生成 (S)-4-(4-Chloro-phenyl)-2-hydroxy-butyric acid ethyl ester 、 (R)-4-(4-Chloro-phenyl)-2-hydroxy-butyric acid ethyl ester
  参考文献：
  名称：

  Deracemisation of aryl substituted α-hydroxy esters using Candida parapsilosis ATCC 7330: effect of substrate structure and mechanism

  摘要：

  Candida parapsilosis ATCC 7330 was found to be an efficient biocatalyst for the deracemisation of aryl alpha-hydroxy esters (65-85% yield and 90-99% ee). A variety of aryl and aryl substituted alpha-hydroxy esters were synthesized to reflect steric and electronic effects on biocatalytic deracemisation. The mechanism of this biocatalytic deracemisation was found to be stereoinversion. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.104
• 作为产物：
  描述：

  4-chlorophenethylmagnesium bromide 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 4-(4-Chloro-phenyl)-2-hydroxy-butyric acid ethyl ester
  参考文献：
  名称：

  减少微生物的立体化学控制。第31部分：在选定的反应条件下通过面包酵母还原2-氧代-4-芳基丁酸烷基酯

  摘要：

  已证明在水-有机溶剂中用苯甲酰氯处理面包酵母是抑制α-羟基酯还原中提供α-羟基酯的（S）-对映异构体的酶的有效方法。该方法对于全细胞系统生产具有高化学产率和高对映体过量的（R）产物是有效的。

  DOI：

  10.1016/s0957-4166(98)00277-8

文献信息

• Process for preparation of 2-oxocarboxylic acid esters
  申请人：——

  公开号：US20040162441A1

  公开（公告）日：2004-08-19

  A process for the preparation of 2-oxocarboxylic acid esters represented by the following general formula (I), comprising by oxidizing a 2-hydroxycarboxylic acid ester represented by the following general formula (II) in the presence of a nitroxyl radical represented by the following general formula (III), a hypochlorite, a metal bromide and water with the pH of the reaction system being kept within the range of 5 to 7: 1 (I) (II) (III) wherein R 1 and R 2 are each independently an alkyl group, an alkenyl group, an alkynyl group, an aryl group or an aralkyl group, which each may be substituted with substituents; and R 3 is a hydrogen atom, an alkoxyl group, an aralkyloxy group, an acyloxy group or a hydroxyl group.

  一种制备由下式通式（I）代表的 2-氧代羧酸酯的工艺，包括在由下式通式（III）代表的硝基、次氯酸盐、金属溴和水的存在下，氧化由下式通式（II）代表的 2-羟基羧酸酯，反应体系的 pH 值保持在 5 至 7 的范围内： 1 (I) (II) (III) 其中 R 1 和 R 2 各自独立地为烷基、烯基、炔基、芳基或芳烷基，各自可被取代基取代；以及 R 3 是氢原子、烷氧基、芳氧基、酰氧基或羟基。
• PROCESS FOR PREPARATION OF 2-OXOCARBOXYLIC ACID ESTERS
  申请人：KURARAY CO., LTD.

  公开号：EP1405841B1

  公开（公告）日：2006-08-16
• US6897335B2
  申请人：——

  公开号：US6897335B2

  公开（公告）日：2005-05-24
• Deracemisation of aryl substituted α-hydroxy esters using Candida parapsilosis ATCC 7330: effect of substrate structure and mechanism
  作者：B. Baskar、N.G. Pandian、K. Priya、Anju Chadha

  DOI：10.1016/j.tet.2005.09.104

  日期：2005.12

  Candida parapsilosis ATCC 7330 was found to be an efficient biocatalyst for the deracemisation of aryl alpha-hydroxy esters (65-85% yield and 90-99% ee). A variety of aryl and aryl substituted alpha-hydroxy esters were synthesized to reflect steric and electronic effects on biocatalytic deracemisation. The mechanism of this biocatalytic deracemisation was found to be stereoinversion. (c) 2005 Elsevier Ltd. All rights reserved.
• Stereochemical control in microbial reduction. Part 31: Reduction of alkyl 2-oxo-4-arylbutyrates by baker's yeast under selected reaction conditions
  作者：Duc Hai Dao、Mutsuo Okamura、Takeshi Akasaka、Yasushi Kawai、Kouichi Hida、Atsuyoshi Ohno

  DOI：10.1016/s0957-4166(98)00277-8

  日期：1998.8

  Treatment of baker's yeast with phenacyl chloride in an aqueous–organic solvent has been proven to be an effective method of inhibiting the enzymes that afford (S)-enantiomers of α-hydroxy esters in the reduction of α-keto esters. The procedure is effective for the whole-cell system to produce the (R)-product with high chemical yield and high enantiomeric excess.

  已证明在水-有机溶剂中用苯甲酰氯处理面包酵母是抑制α-羟基酯还原中提供α-羟基酯的（S）-对映异构体的酶的有效方法。该方法对于全细胞系统生产具有高化学产率和高对映体过量的（R）产物是有效的。