methyl (3S)-3-phenyl-4-pentenoate

• 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 (3S)-3-phenyl-4-pentenoate
• 英文别名: methyl 3-phenyl-4-pentenoate；methyl (3S)-3-phenylpent-4-enoate
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: IFSXZCHDQCEJHG-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (3S)-3-phenyl-4-pentenoate 在 臭氧 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以80%的产率得到(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  铱催化2-（4-硝基苯基磺酰基）乙酸甲酯的对映体选择性烯丙基烷基化及其后续转化

  摘要：

  2-（4-硝基苯基磺酰基）乙酸甲酯的高度对映选择性烯丙基烷基化反应在铱催化系统的存在下进行。产物的后续转化，包括还原性脱磺酰化和改性的朱莉娅烯化，导致乙酸甲酯或丙烯酸甲酯的烯丙基烷基化产物具有良好的收率和高对映选择性。

  DOI：

  10.1002/adsc.201200113
• 作为产物：
  描述：

  1-{2-[(S_S)-(p-tolylsulfinyl)]}pyrrolyl cinnamate 在 copper(l) iodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 methyl (3S)-3-phenyl-4-pentenoate
  参考文献：
  名称：

  在芳基铜试剂共轭加成手性亚磺酰基取代的吡咯基α，β-不饱和酰胺过程中的1,6-不对称诱导。

  摘要：

  衍生自芳基格氏试剂的芳基铜试剂和碘化铜（I）向手性1- [2-（对甲苯磺酰亚胺基）]吡咯基肉桂酰胺的不对称共轭加成反应顺利进行，得到具有高非对映选择性（>或=的（3R）-加合物高收率达92％de）。将肉桂酰胺与烷基格氏试剂-碘化铜的混合物共轭添加，或者将巴豆酰胺衍生物与芳基格氏试剂-碘化铜的碘化物共轭添加，可得到中等至良好的非对映选择性。用这些亚磺酰基吡咯基α，β-不饱和酰胺，可以有效地回收手性助剂，而在不对称共轭物添加后没有光学纯度的损失。

  DOI：

  10.1248/cpb.49.1609

文献信息

• Extremely Efficient Chiral Induction in Conjugate Additions of <i>p</i>-Tolyl α-Lithio-β-(trimethylsilyl)ethyl Sulfoxide and Subsequent Electrophilic Trapping Reactions
  作者：Shuichi Nakamura、Yoshihiko Watanabe、Takeshi Toru

  DOI：10.1021/jo991635n

  日期：2000.3.1

  Reaction of p-tolyl alpha-lithio-beta-(trimethylsilyl)ethyl sulfoxide with alpha,beta-unsaturated esters gave the conjugate addition products as a single diastereomer. The intermediate enolates were subsequently trapped with various alkyl halides or aldehydes to give the products with extremely high stereoselectivity. The reaction with alpha,beta-unsaturated ketones also proceeded with high diastereoselectivity

  对-甲苯基α-硫代-β-（三甲基甲硅烷基）乙基亚砜与α，β-不饱和酯的反应得到共轭加成产物，为单一非对映异构体。随后将中间体烯醇化物用各种烷基卤化物或醛捕获，以提供具有极高立体选择性的产物。与α，β-不饱和酮的反应也以高非对映选择性进行。衍生自α-甲基-α，β-不饱和酯的烯醇化物的质子分解得到具有高立体选择性的产物。亚砜基的立体和区域选择性消除得到手性均烯丙基羧酸盐。
• 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
  作者：Anna Brodzka、Dominik Koszelewski、Malgorzata Cwiklak、Ryszard Ostaszewski

  DOI：10.1016/j.tetasy.2013.02.016

  日期：2013.4

  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.
• The studies on chemoenzymatic synthesis of Femoxetine
  作者：Anna Brodzka、Dominik Koszelewski、Ryszard Ostaszewski

  DOI：10.1016/j.molcatb.2012.06.009

  日期：2012.10

  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.
• Iridium-Catalyzed Enantioselective Allylic Alkylation of Methyl 2-(4-nitrophenylsulfonyl)acetate and Subsequent Transformations
  作者：Qing-Long Xu、Li-Xin Dai、Shu-Li You

  DOI：10.1002/adsc.201200113

  日期：2012.8.13

  Highly enantioselective allylic alkylation reactions of methyl 2-(4-nitrophenylsulfonyl)acetate were carried out in the presence of an iridium catalytic system. The subsequent transformations of the products including reductive desulfonylation and modified Julia olefination led to the allylic alkylation products of methyl acetate or methyl acrylate with good yields and high enantioselectivity.

  2-（4-硝基苯基磺酰基）乙酸甲酯的高度对映选择性烯丙基烷基化反应在铱催化系统的存在下进行。产物的后续转化，包括还原性脱磺酰化和改性的朱莉娅烯化，导致乙酸甲酯或丙烯酸甲酯的烯丙基烷基化产物具有良好的收率和高对映选择性。
• 1,6-Asymmetric Induction during the Conjugate Addition of Arylcopper Reagents to a Chiral Sulfinyl-Substituted Pyrrolyl .ALPHA., .BETA.-Unsaturated Amide.
  作者：Yoshitsugu ARAI、Kimio UEDA、Jianhua XIE、Yukio MASAKI

  DOI：10.1248/cpb.49.1609

  日期：——

  The asymmetric conjugate addition of arylcopper reagents derived from aryl Grignard reagents and copper(I) iodide to a chiral 1-[2-(p-tolylsulfinyl)]pyrrolyl cinnamide proceeded smoothly to give (3R)-adducts with high diastereoselectivities (> or =92% de) in high yields. Conjugate additions either of the cinnamide with the alkyl Grignard reagent-copper(l) iodide combination or of the crotonamide derivative

  衍生自芳基格氏试剂的芳基铜试剂和碘化铜（I）向手性1- [2-（对甲苯磺酰亚胺基）]吡咯基肉桂酰胺的不对称共轭加成反应顺利进行，得到具有高非对映选择性（>或=的（3R）-加合物高收率达92％de）。将肉桂酰胺与烷基格氏试剂-碘化铜的混合物共轭添加，或者将巴豆酰胺衍生物与芳基格氏试剂-碘化铜的碘化物共轭添加，可得到中等至良好的非对映选择性。用这些亚磺酰基吡咯基α，β-不饱和酰胺，可以有效地回收手性助剂，而在不对称共轭物添加后没有光学纯度的损失。