3-hydroxy-5-phenyl-pent-4-enoic acid | 156520-66-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: 3-hydroxy-5-phenyl-pent-4-enoic acid
• 英文别名: 3-hydroxy-5-phenylpent-4-enoic acid
• CAS: 156520-66-0
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: JKDYSKHGCXBPQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 3-hydroxy-5-phenylpent-4-enoate 在 immobilized Candida parapsilosis ATCC 7330 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以28%的产率得到ethyl (S)-3-hydroxy-5-phenylpent-4-enoate
  参考文献：
  名称：

  Deracemisation of aromatic β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330 and determination of absolute configuration by 1H NMR

  摘要：

  Deracemisation of aryl and substituted aryl P-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330 yields the corresponding (S)-enantiomer in >99% enantiomeric excess and good yield (up to 68%). The absolute configuration of ethyl 3-(2,4-dichlorophenyl)-3-hydroxy propanoate and ethyl 3-hydroxy-5-phenyl-pent-4-enoate as determined by H-1 NMR using MTPA chloride was found to be 'S'. The chemical shifts of the methoxy groups of the two diastereomeric MTPA esters were used as diagnostic signals to determine the absolute configuration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.017

文献信息

• Deracemisation of aromatic β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330 and determination of absolute configuration by 1H NMR
  作者：Santosh Kumar Padhi、Anju Chadha

  DOI：10.1016/j.tetasy.2005.07.017

  日期：2005.8

  Deracemisation of aryl and substituted aryl P-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330 yields the corresponding (S)-enantiomer in >99% enantiomeric excess and good yield (up to 68%). The absolute configuration of ethyl 3-(2,4-dichlorophenyl)-3-hydroxy propanoate and ethyl 3-hydroxy-5-phenyl-pent-4-enoate as determined by H-1 NMR using MTPA chloride was found to be 'S'. The chemical shifts of the methoxy groups of the two diastereomeric MTPA esters were used as diagnostic signals to determine the absolute configuration. (c) 2005 Elsevier Ltd. All rights reserved.