methyl 2-hydroxy-4-phenylbut-3-ynoate | 1271182-93-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-hydroxy-4-phenylbut-3-ynoate
• 英文别名: Methyl 2-hydroxy-4-phenylbut-3-ynoate
• CAS: 1271182-93-4
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: HGBTWLKDTOKBCF-UHFFFAOYSA-N

物化性质

• 沸点：
  318.1±32.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 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

• 作为反应物：
  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
• 作为产物：
  描述：

  methyl 2-oxo-4-phenylbut-3-ynoate 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 叔丁醇 作用下， 反应 0.5h， 生成 methyl 2-hydroxy-4-phenylbut-3-ynoate
  参考文献：
  名称：

  NaBH4和CeCl3·7H2O介导的α-酮基丙炔酸酯的化学选择性还原和酯交换反应

  摘要：

  摘要 描述了使用 NaBH4 与 CeCl3·7H2O 组合通过化学选择性还原和酯交换反应有效地一锅法合成 α-羟基炔丙酯。

  DOI：

  10.1080/00397911.2010.502993

文献信息

• Biocatalytic deracemization of alkyl-2-hydroxy-4-arylbut-3-ynoates using whole cells of Candida parapsilosis ATCC 7330
  作者：Thangavel Saravanan、Anju Chadha

  DOI：10.1016/j.tetasy.2010.11.021

  日期：2010.12

  Racemic alkyl-2-hydroxy-4-arylbut-3-ynoates were deracemized to the (S)-alky1-2-hydroxy-4-arylbut-3-ynoates in excellent enantiomeric excesses (up to >99%) and good isolated yields (up to 81%) with the biocatalyst Candida parapsilosis ATCC 7330. The absolute configuration of the resulting enantiomer was assigned by H-1 NMR using Mosher's method. (C) 2010 Elsevier Ltd. All rights reserved.