(2S)-(E)-2-Hydroxy-4-phenylbut-3-enoic acid ethyl ester | 121155-45-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (2S)-(E)-2-Hydroxy-4-phenylbut-3-enoic acid ethyl ester
• 英文别名: (S,E)-ethyl 2-hydroxy-4-phenylbut-3-enoate；ethyl (S,E)-2-hydroxy-4-phenylbut-3-enoate；(S)-ethyl 2-hydroxy-4-phenylbut-3-enoate；ethyl (E)-2-hydroxy-4-phenylbut-3-enoate；ethyl (E,2S)-2-hydroxy-4-phenylbut-3-enoate
• CAS: 121155-45-1
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: VKJBHXYAEPBVRG-FBOQAHMBSA-N

物化性质

• 沸点：
  347.0±30.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (2S)-(E)-2-Hydroxy-4-phenylbut-3-enoic acid ethyl ester 在 吡啶 作用下， 反应 24.0h， 生成 (E)-(S)-4-Phenyl-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-3-enoic acid ethyl ester
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2004.11.002
• 作为产物：
  描述：

  rac-(E)-ethyl 2-hydroxy-4-phenylbut-3-enoate 在 Candida parapsilosis ATCC 7330 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以78%的产率得到(2S)-(E)-2-Hydroxy-4-phenylbut-3-enoic acid ethyl ester
  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

• Cobalt-Catalyzed Enantioselective Vinylation of Activated Ketones and Imines
  作者：Yuan Huang、Rui-Zhi Huang、Yu Zhao

  DOI：10.1021/jacs.6b02372

  日期：2016.5.25

  We present here an unprecedented cobalt-catalyzed enantioselective vinylation of α-ketoesters, isatins, and imines to deliver a range of synthetically useful allylic alcohols and amines in high enantiopurity. This method employs commercially available and easy to handle catalysts and reagents and exhibits a high degree of practicality. The efficiency, selectivity, and operational simplicity of this

  我们在此展示了一种前所未有的钴催化的 α-酮酯、靛红和亚胺的对映选择性乙烯基化，以提供一系列具有高对映纯度的合成有用的烯丙醇和胺。该方法采用市售且易于处理的催化剂和试剂，具有很高的实用性。该催化系统的效率、选择性和操作简单性加上底物的通用性使该方法成为有机合成中的宝贵工具。
• Asymmetric Nucleophilic Acylation of Aldehydes via 1,1-Heterodisubstituted Alkenes
  作者：Holger Monenschein、Gerald Dräger、Alexander Jung、Andreas Kirschning

  DOI：10.1002/(sici)1521-3765(19990802)5:8<2270::aid-chem2270>3.0.co;2-l

  日期：1999.8.2

  Aldehydes are asymmetrically acylated by a two step sequence that is initiated by a homologation step to 1,1-heterodisubstituted alkenes followed by asymmetric dihydroxylation. Thus, ketene O,S-acetals are efficiently prepared from aldehydes by a Peterson olefination with lithiated methoxy-phenylthiotrimethylsilyl methane 14 as the C-1 source. Although they are dihydroxylated with the Sharpless catalyst with moderate to good enantioselectivity (62-80% ee), the process is not efficient owing to the low chemical yields of the desired alpha-hydroxy methyl esters (7-37%). Use of the corresponding sulfoxide 24 or sulfon 25 led to an improved chemical yield of alpha-hydroxy methyl ester 19, but the stereoselectivity was diminished. In contrast, intermediate ketene O,O-acetals are prepared by a Horner-Wittig reaction with phosphine oxide 31 and are dihydroxylated both with good chemical and stereochemical yield. The concept is applicable to aromatic, aliphatic, and chiral aldehydes. For example, this short sequence allows exclusive and independent preparation of both diastereomeric heptoses 69a and 69b.
• A New Asymmetric Formylation of Aldehydes
  作者：Andreas Kirschning、Gerald Dräger、Alexander Jung

  DOI：10.1002/anie.199702531

  日期：1997.2.14
• 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.
• Highly Enantioselective Sequential Hydrogenation of Ethyl 2-Oxo-4-arylbut-3-enoate to Ethyl 2-Hydroxy-4-arylbutyrate
  作者：Qinghua Meng、Lufeng Zhu、Zhaoguo Zhang

  DOI：10.1021/jo801140j

  日期：2008.9.19

  The hydrogenation of (E)-ethyl 2-oxo-4-arylbut-3-enoate with [NH2Me2](+)[RuCl [(S)-SunPhos]}2(mu-Cl-3] gave ethyl 2-hydroxy-4-arylbutyrate with 94-96% ee. Further investigation has proved that the hydrogenation proceeded via a sequential hydrogenation of C = O and C = C bonds, which is sensitive to the reaction temperature. Hydrolysis of ethyl 2-hydroxy-4-phenylbutyrate (ee 93%) provided the 2-hydroxy-4-phenylbutyric acid with 81 % yield at 99% ee after a single recrystallization from 1, 2-dichloroethylene.