rac-(Z)-methyl 2-hydroxy-4-phenylbut-3-enoate | 135267-89-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: rac-(Z)-methyl 2-hydroxy-4-phenylbut-3-enoate
• 英文别名: methyl (Z)-2-hydroxy-4-phenylbut-3-enoate
• CAS: 135267-89-9
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: XVWDLSYYNQHVGI-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 2-hydroxy-4-phenylbut-3-ynoate 在 喹啉 、 氢气 作用下， 以 乙醇 为溶剂， 生成 rac-(Z)-methyl 2-hydroxy-4-phenylbut-3-enoate
  参考文献：
  名称：

  Stereochemical preference of Candida parapsilosis ATCC 7330 mediated deracemization: E- versus Z-aryl secondary alcohols

  摘要：

  The stereochemical preference of the biocatalyst, Candida parapsilosis ATCC 7330, was investigated with respect to the E/Z configuration in the deracemization and the asymmetric reduction of aryl secondary alcohols and prochiral ketones, respectively. The biocatalyst preferred the E-isomers over Z-isomers as substrates as evidenced from the experimental results of > 99% ee and up to 86% isolated yield for E-secondary alcohols. The synthesis of enantiomerically pure E-4-phenylbut-3-ene-1,2-diol (ee > 99%, isolated yield 86%) by whole cell mediated deracemization is reported here for the first time. The geometric preference of the enzymes was confirmed by using the cell free extract of this biocatalyst. Mechanistic insights using in silico studies showed that the E-isomers when located in the active site are favourably placed with respect to the catalytic triad (Ser-Tyr-Lys) for hydride transfer from NADPH. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.014

文献信息

• A new vinylsilane substitution reaction with glyoxylate: asymmetric synthesis of .alpha.-hydroxy .beta.,.gamma.-unsaturated esters
  作者：Koichi Mikami、Hideaki Wakabayashi、Takeshi Nakai

  DOI：10.1021/jo00014a002

  日期：1991.7

  The vinylsilane substitution reaction with glyoxylate and the asymmetric version thereof are described. These new reactions provide alpha-hydroxy beta, gamma-unsaturated esters of biological and synthetic importance in high enantiomeric and geometric purity.
• Stereochemical preference of Candida parapsilosis ATCC 7330 mediated deracemization: E- versus Z-aryl secondary alcohols
  作者：Thangavelu Saravanan、Rajendran Selvakumar、Mukesh Doble、Anju Chadha

  DOI：10.1016/j.tetasy.2012.09.014

  日期：2012.10

  The stereochemical preference of the biocatalyst, Candida parapsilosis ATCC 7330, was investigated with respect to the E/Z configuration in the deracemization and the asymmetric reduction of aryl secondary alcohols and prochiral ketones, respectively. The biocatalyst preferred the E-isomers over Z-isomers as substrates as evidenced from the experimental results of > 99% ee and up to 86% isolated yield for E-secondary alcohols. The synthesis of enantiomerically pure E-4-phenylbut-3-ene-1,2-diol (ee > 99%, isolated yield 86%) by whole cell mediated deracemization is reported here for the first time. The geometric preference of the enzymes was confirmed by using the cell free extract of this biocatalyst. Mechanistic insights using in silico studies showed that the E-isomers when located in the active site are favourably placed with respect to the catalytic triad (Ser-Tyr-Lys) for hydride transfer from NADPH. (C) 2012 Elsevier Ltd. All rights reserved.