(R)-(+)-3-phenyl-4-pentenoic acid ethyl ester | 1311201-63-4

• 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: (R)-(+)-3-phenyl-4-pentenoic acid ethyl ester
• 英文别名: ethyl 3-phenylpent-4-enoate；ethyl (R)-3-phenylpent-4-enoate；(R)-ethyl 3-phenylpent-4-enoate；ethyl 3-phenyl-4-pentenoate；ethyl (3R)-3-phenylpent-4-enoate
• CAS: 1311201-63-4
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: SNMOKXQMVVHRQM-NSHDSACASA-N

物化性质

• 沸点：
  261.5±9.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(+)-3-phenyl-4-pentenoic acid ethyl ester 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以40%的产率得到(S)-4-Oxo-3-phenyl-butyric acid ethyl ester
  参考文献：
  名称：

  Studies on the chemoenzymatic synthesis of 3-phenyl-GABA and 4-phenyl-pyrrolid-2-one: the influence of donor of the alkoxy group on enantioselective esterification

  摘要：

  A new chemoenzymatic method for the synthesis of enantiomerically pure 3-phenyl-gamma-aminobutyric acid 1 and 4-phenyl-pyrrolid-2-one 9 based on the enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid 2 is described herein. Enzymatic resolution of the racemic substrate provided products with good enantiselectivity upon esterification. In these reactions, a new class of alkoxy group donor-orthoesters, acetals and ketals were used. The best results of the enzymatic kinetic resolution were obtained for triethyl orthoacetate in toluene solvent. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.016
• 作为产物：
  描述：

  3-phenylpent-4-enoic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (R)-(+)-3-phenyl-4-pentenoic acid ethyl ester
  参考文献：
  名称：

  The studies on chemoenzymatic synthesis of Femoxetine

  摘要：

  The studies on enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid esters were performed. The obtained results demonstrated that the careful choice of biocatalyst and a reaction type are very important for successful enzymatic kinetic resolution. Kinetic resolution provides 3-phenyl-4-pentenoic acid (1) with good enantioselectivity upon esterification. That product was used as a substrate for formal synthesis of two biologically relevant compounds Femoxetine and LG 121071. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.06.009

文献信息

• Dynamic Kinetic Resolution of 3-Aryl-4-pentenoic Acids
  作者：Dominik Koszelewski、Anna Brodzka、Anna Żądło、Daniel Paprocki、Damian Trzepizur、Małgorzata Zysk、Ryszard Ostaszewski

  DOI：10.1021/acscatal.6b00271

  日期：2016.5.6

  The first example of dynamic kinetic resolution (DKR) of chiral unsaturated carboxylic acids is described. The application of tandem metal–enzyme DKR is a powerful tool for the manufacture of high-value chemical commodities. This new protocol of kinetic resolution based on irreversible enzymatic esterification of 3-aryl-4-pentenoic acids with ortho esters was introduced to obtain optically active unsaturated

  描述了手性不饱和羧酸的动态动力学拆分（DKR）的第一个例子。串联金属酶DKR的应用是制造高价值化学商品的强大工具。引入了基于3-芳基-4-戊烯酸与原酸酯的不可逆酶促酯化反应的动力学拆分新方案，以获得旋光性不饱和羧酸。该方法与目标底物的金属催化消旋作用相结合，从而提供了光学纯度很高的3-苯基戊-4-烯酸乙酯的S对映体，分离产率很高（98％）。注意到有机助溶剂和金属催化剂对酶动力学动力学拆分的转化率和对映选择性的重大影响。
• A Chiral Bidentate sp2-N Ligand, Naph-diPIM: Application to CpRu-Catalyzed Asymmetric Dehydrative C-, N-, and O-Allylation
  作者：Kengo Miyata、Hironori Kutsuna、Sho Kawakami、Masato Kitamura

  DOI：10.1002/anie.201100772

  日期：2011.5.9