(R)-(-)-vinyl 3-phenylbutanoate | 221878-55-3

• 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)-(-)-vinyl 3-phenylbutanoate
• 英文别名: D-3-phenyl-butyric acid vinyl ester；D-3-Phenyl-buttersaeure-vinylester；ethenyl (3R)-3-phenylbutanoate
• CAS: 221878-55-3
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: VYATZCPFHGSBPG-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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

• 作为产物：
  描述：

  (+/-)-3-苯基丁酸 在 Chromobacterium Viscosum lipase 、 cyclohexane-1,3-dione resin bound 、 mercury(II) diacetate 作用下， 以 phosphate buffer 为溶剂， 反应 22.08h， 生成 (R)-(-)-vinyl 3-phenylbutanoate
  参考文献：
  名称：

  Lipase-Catalyzed Kinetic Resolution on Solid-Phase via a “Capture and Release” Strategy

  摘要：

  The lipase-catalyzed kinetic resolution of (R/S)-3-phenylbutyric acid 2 using solid-supported cyclohexane-1,3-dione (CHD) 6 is described. In each case the predominant enantiomer observed, after cleavage from the resin, was (R)-(-)-3-phenylbutyric acid (R)-2 (ee > 99%) rather than the expected (S)-enantiomer of 2. This observation is in contrast to the fact that Chromobacterium viscosum lipase shows high enantiospecificity for the (S)-enantiomer in the corresponding solution-phase hydrolysis reactions. The (R)-acyl group was subsequently released from the resin by NaOH hydrolysis, and the yield of the reaction could be improved by triple acylation of the resin.

  DOI：

  10.1021/ja037922x

文献信息

• Optically Active Polymers from Active Vinyl Esters. A Convenient Method of Studying the Kinetics of Polymerization¹
  作者：C. S. Marvel、Joseph Dec、Harold G. Cooke

  DOI：10.1021/ja01869a059

  日期：1940.12
• Improvement of enantioselectivity in kinetic resolution of a primary alcohol through lipase-catalyzed transesterification by using a chiral acyl donor
  作者：Keiji Hirose、Hiroyuki Naka、Masashi Yano、Sozaburo Ohashi、Koichiro Naemura、Yoshito Tobe

  DOI：10.1016/s0957-4166(00)00060-4

  日期：2000.3

  The enantioselectivity of the kinetic resolution of a primary alcohol which has a chiral center at the beta-position of the hydroxyl group was substantially improved by employing a racemic mixture of a chiral acyl donor for enantioselective transesterification catalyzed by a lipase. The combination of the lipase, solvent, and acyl donor was also effective for the enantioselectivity. In addition, the important effect of the chirality of an acyl donor on kinetic resolution was investigated by using enantiomerically pure acyl donors. Here we demonstrate the effective kinetic resolution (E=98) of a primary alcohol, 2-phenyl-1-propanol, by using a racemic mixture of a chiral acyl donor, vinyl 3-phenylbutanoate. (C) 2000 Elsevier Science Ltd. All rights reserved.
• The Use of Vinyl Esters Significantly Enhanced Enantioselectivities and Reaction Rates in Lipase-Catalyzed Resolutions of Arylaliphatic Carboxylic Acids
  作者：Hong Yang、Erik Henke、Uwe T. Bornscheuer

  DOI：10.1021/jo981780l

  日期：1999.3.1
• US6365398B1
  申请人：——

  公开号：US6365398B1

  公开（公告）日：2002-04-02
• Lipase-Catalyzed Kinetic Resolution on Solid-Phase via a “Capture and Release” Strategy
  作者：Cara E. Humphrey、Nicholas J. Turner、Morag A. M. Easson、Sabine L. Flitsch、Rein V. Ulijn

  DOI：10.1021/ja037922x

  日期：2003.11.1

  The lipase-catalyzed kinetic resolution of (R/S)-3-phenylbutyric acid 2 using solid-supported cyclohexane-1,3-dione (CHD) 6 is described. In each case the predominant enantiomer observed, after cleavage from the resin, was (R)-(-)-3-phenylbutyric acid (R)-2 (ee > 99%) rather than the expected (S)-enantiomer of 2. This observation is in contrast to the fact that Chromobacterium viscosum lipase shows high enantiospecificity for the (S)-enantiomer in the corresponding solution-phase hydrolysis reactions. The (R)-acyl group was subsequently released from the resin by NaOH hydrolysis, and the yield of the reaction could be improved by triple acylation of the resin.