(R)-3-乙酰氧基-3-苯基丙酸乙酯 | 37504-79-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (R)-3-乙酰氧基-3-苯基丙酸乙酯
• 英文名称: (R)-ethyl 3-acetoxy-3-phenylpropanoate
• 英文别名: (R)-3-acetoxy-3-phenyl-propionic acid ethyl ester；(R)-3-Acetoxy-3-phenyl-propionsaeure-aethylester；ethyl (3R)-3-acetyloxy-3-phenylpropanoate
• CAS: 37504-79-3
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: HNOFMAVEDATAJR-GFCCVEGCSA-N

物化性质

• 沸点：
  268.4±20.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-羟基-3-苯丙酸 在 乙醇 、 乙酸酐 作用下， 生成 (R)-3-乙酰氧基-3-苯基丙酸乙酯
  参考文献：
  名称：

  所述的397.瓦尔登翻转反应p -toluenesulphinic和p乙基甲苯磺酸酯d -β羟基-β-苯基

  摘要：

  DOI：

  10.1039/jr9350001663

文献信息

• Synthesis of Novel Diastereomeric Diphosphine Ligands and Their Applications in Asymmetric Hydrogenation Reactions
  作者：Liqin Qiu、Jianying Qi、Cheng-Chao Pai、Shusun Chan、Zhongyuan Zhou、Michael C. K. Choi、Albert S. C. Chan

  DOI：10.1021/ol026817+

  日期：2002.12.1

  Diastereomeric biaryl diphosphine ligands 10 and 11 with added chiral centers on the backbone were synthesized. Substrate-directed asymmetric synthesis occurred in the coupling step of the preparation of the diastereomeric diphosphine oxides. The diastereomeric diphosphine oxides were easily separated by column chromatography with silica gel. Ruthenium catalysts containing these ligands were highly effective

  ［结构：见正文］合成了在主链上增加了手性中心的非对映体联芳基二膦配体10和11。在非对映体二膦氧化物的制备的偶联步骤中发生了底物定向的不对称合成。通过使用硅胶的柱色谱法容易地分离非对映体二膦氧化物。含有这些配体的钌催化剂在2-（6'-甲氧基-2'-萘基）丙酸和β-酮酸酯的氢化中非常有效。额外的手性中心对催化剂的对映选择性和活性有重大影响。
• Enantioselective Synthesis of β-Hydroxy Acid Derivatives via a One-Pot Aldol Reaction−Dynamic Kinetic Resolution
  作者：Fernando F. Huerta、Jan-E. Bäckvall

  DOI：10.1021/ol015682p

  日期：2001.4.1

  [reaction: see text]. Combining dynamic kinetic resolution with an aldol reaction provides access to beta-hydroxy ester derivatives with high enantiomeric purity (up to 99% ee) in a one-pot procedure. Only simple starting materials are required in this enantioselective process, and preformation of a silyl enol ether is not necessary.

  [反应：请参见文字]。将动态动力学拆分与醛醇缩合反应相结合，可在一锅法中获得具有高对映体纯度（最高99％ee）的β-羟基酯衍生物。在该对映选择性过程中仅需要简单的起始原料，并且不需要甲硅烷基烯醇醚的预形成。
• Access to Optically Pure β-Hydroxy Esters via Non-Enzymatic Kinetic Resolution by a Planar-Chiral DMAP Catalyst
  作者：Alba Díazlvarez、Laura Mesas-Sánchez、Peter Dinér

  DOI：10.3390/molecules190914273

  日期：——

  The development of new approaches to obtain optically pure β-hydroxy esters is an important area in synthetic organic chemistry since they are precursors of other high value compounds. Herein, the kinetic resolution of racemic β-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic β-hydroxy esters was obtained in excellent selectivities

  开发获得光学纯 β-羟基酯的新方法是合成有机化学中的一个重要领域，因为它们是其他高价值化合物的前体。本文介绍了使用平面手性 DMAP 衍生物催化剂对外消旋 β-羟基酯进行动力学拆分。按照此程序，以优异的选择性（高达 s = 107）和高对映体过量（高达 99% ee）获得了一系列芳族 β-羟基酯。此外，本方法的效用在 (S)-3-羟基-N-甲基-3-苯基丙酰胺的合成中得到了证明，这是一种生物活性分子的关键中间体，如氟西汀、托莫西汀或尼索西汀，以其对映体纯的形式存在。
• Lipases A and B from Candida antarctica in the enantioselective acylation of ethyl 3-heteroaryl-3-hydroxypropanoates: aspects on the preparation and enantiopreference
  作者：Jürgen Brem、Arto Liljeblad、Csaba Paizs、Monica Ioana Toşa、Florin-Dan Irimie、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2011.01.027

  日期：2011.2

  The preparative scale kinetic resolution of racemic ethyl 2- and 3-furyl- and 2- and 3-thienyl-3-hydroxypropanoates has been performed by Candida antarctica lipases A and B with vinyl esters. A study based on the present work together with the literature has been carried out in terms of lipase enantiopreference and substrate structure. We also discuss the excellent behavior of the lipase A in O-acylations of secondary alcohols with respect to enantiopreference. (C) 2011 Elsevier Ltd. All rights reserved.
• Thermomorphic System with Non-Fluorous Phase-Tagged Ru(BINAP) Catalyst:  Facile Liquid/Solid Catalyst Separation and Application in Asymmetric Hydrogenation
  作者：Yi-Yong Huang、Yan-Mei He、Hai-Feng Zhou、Lei Wu、Bao-Lin Li、Qing-Hua Fan

  DOI：10.1021/jo052092m

  日期：2006.3.31

  The thermomorphic BINAP derivative 1 tagged with long alkyl chains was prepared from (S)-5,5'-diamino BINAP and applied to Ru-catalyzed asymmetric hydrogenation of beta-ketoesters under homogeneous conditions in 3:1 (v/v) ethanol/1,4-dioxane at 60 degrees C with high enantioselectivity (up to 98% ee). Results indicated that the Ru(1) catalyst was easily recovered by simple cooling and precipitation and could be used for at least four cycles without any loss of enantioselectivity.