(S)-isopropyl 2-hydroxy-4-phenylbut-3-ynoate | 1271183-34-6

• 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: (S)-isopropyl 2-hydroxy-4-phenylbut-3-ynoate
• 英文别名: propan-2-yl (2S)-2-hydroxy-4-phenylbut-3-ynoate
• CAS: 1271183-34-6
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: MWTGPGDIGASYIZ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  isopropyl 2-hydroxy-4-phenylbut-3-ynoate 在 Candida parapsilosis ATCC 7330 作用下， 以 水 为溶剂， 反应 2.0h， 以72%的产率得到(S)-isopropyl 2-hydroxy-4-phenylbut-3-ynoate
  参考文献：
  名称：

  Biocatalytic deracemization of alkyl-2-hydroxy-4-arylbut-3-ynoates using whole cells of Candida parapsilosis ATCC 7330

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2010.11.021

文献信息

• Enantioselective Meerwein–Ponndorf–Verley reduction of β,γ-unsaturated α-keto esters by asymmetric binary-acid catalysis in the green solvent iPrOH
  作者：Huixin Qiu、Jiayi Ren、Long Zhang、Ran Song、Wen Si、Daoshan Yang、Lirong Wen、Jian Lv

  DOI：10.1039/d2gc03441g

  日期：——

  of β,γ-unsaturated α-keto esters in iPrOH alone was achieved by using asymmetric binary-acid catalysts. The presence of 0.2 mol% of a chiral phosphoric acid and 0.5 mol% Sc(OTf)3 is sufficient to obtain synthetically relevant β,γ-unsaturated α-hydroxy esters in excellent yields (up to 98%) and enantioselectivities (up to 99% ee). By DFT studies on the transfer hydrogenation of 2-oxo-3-enoates, we have

  通过使用不对称二元酸催化剂，单独在 iPrOH 中实现了 β,γ-不饱和 α-酮酯的对映选择性 Meerwein-Ponndorf-Verley 还原。0.2 mol% 的手性磷酸和 0.5 mol% Sc(OTf) 3的存在足以以优异的收率（高达 98%）和对映选择性（高达 99 %ee)。通过对 2-oxo-3-enoates 转移氢化的 DFT 研究，我们提出了一种可能的机制来阐明二元酸协同效应，并通过底物的乙烯基苯部分和手性磷酸的苯环。
• 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.