(E)-2-Hydroxy-4-p-tolyl-but-3-enoic acid ethyl ester | 830319-58-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-2-Hydroxy-4-p-tolyl-but-3-enoic acid ethyl ester
• 英文别名: ethyl (E)-2-hydroxy-4-(4-methylphenyl)but-3-enoate
• CAS: 830319-58-9
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: QQMGHTZWWMESDT-CMDGGOBGSA-N

物化性质

• 沸点：
  363.8±30.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-2-Hydroxy-4-p-tolyl-but-3-enoic acid ethyl ester 在 Candida parapsilosis ATCC 7330 cells 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 (E)-(S)-2-Hydroxy-4-p-tolyl-but-3-enoic acid ethyl ester 、 (E)-(R)-2-Hydroxy-4-p-tolyl-but-3-enoic 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：

  乙醇 、 acide hydroxy-2 (methyl-4' phenyl)-4 butene-3 oique 在 phospho-tungstic acid 、 phosphotungstic acid 作用下， 以 甲苯 为溶剂， 反应 9.0h， 以73%的产率得到(E)-2-Hydroxy-4-p-tolyl-but-3-enoic 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

文献信息

• Asymmetric reduction of alkyl 2-oxo-4-arylbutanoates and -but-3-enoates by Candida parapsilosis ATCC 7330: assignment of the absolute configuration of ethyl 2-hydroxy-4-(p-methylphenyl)but-3-enoate by 1H NMR
  作者：Baburaj Baskar、N. Ganesh Pandian、Kuttikode Priya、Anju Chadha

  DOI：10.1016/j.tetasy.2004.11.002

  日期：2004.12

  Enantioselective bioreduction of alkyl 2-oxo-4-arylbutanoates and 2-oxo-4-arylbut-3-enoates mediated by Candida parapsilosis ATCC 7330 resulted in the formation of the corresponding (S)-2-hydroxy compounds in high enantiomeric excesses (93-99%) and good isolated yields (58-71%). The absolute configuration of enantiomerically pure ethyl 2-hydroxy-4-(p-methylphenyl)but-3-enoate obtained by the reduction of the corresponding keto ester was assigned by H-1 NMR using Mosher's method. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.