(+/-)-3-acetyloxy-3-phenylpropanenitrile | 82782-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-3-acetyloxy-3-phenylpropanenitrile
• 英文别名: 3-acetoxy-3-phenylpropanenitrile；(2-Cyano-1-phenylethyl) acetate
• CAS: 82782-11-4
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: IOINVUDAFYPKGX-UHFFFAOYSA-N

物化性质

• 沸点：
  327.9±30.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-3-acetyloxy-3-phenylpropanenitrile 在 aluminum oxide 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以96%的产率得到肉桂腈
  参考文献：
  名称：

  Andersen, Soeren H.; Das, Nalin B.; Joergensen, Ruth D., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 1, p. 1 - 14

  摘要：

  DOI：
• 作为产物：
  描述：

  5-phenyl-4,5-dihydroisoxazole 在 sodium methylate 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (+/-)-3-acetyloxy-3-phenylpropanenitrile
  参考文献：
  名称：

  Andersen, Soeren H.; Das, Nalin B.; Joergensen, Ruth D., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 1, p. 1 - 14

  摘要：

  DOI：

文献信息

• Zinc-promoted reactions. 9. The fate of the cyano group in the reduction of simple cyanoketones and N-cyanoamines
  作者：Maria Luisa Di Vona、Luciana Luchetti、Vittorio Rosnati

  DOI：10.1016/s0040-4020(01)85302-3

  日期：1994.1

  The Zn/AcOH reduction of 1 leads only to the carbonyl reduction, while C-decyanation occurs in the case of 2. The mechanism of the latter reaction is discussed. The N-decyanation of N-cyanoamines 3 and 4 involves an ionic mechanism, leading to N-acyl derivatives and isocyanic acid, the latter compound being ultimately reduced to formic acid.

  Zn / AcOH还原为1仅导致羰基还原，而C在2的情况下发生C-脱氰。讨论了后者反应的机理。N-氰胺3和4的N-脱氰涉及离子机理，导致N-酰基衍生物和异氰酸，后者最终被还原为甲酸。
• Chemoenzymatic synthesis2 of both enantiomers of fluoxetine, tomoxetine and nisoxetine: lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles
  作者：Ahmed Kamal、G.B.Ramesh Khanna、R. Ramu

  DOI：10.1016/s0957-4166(02)00537-2

  日期：2002.9

  transesterification process in hydrophobic solvents (diisopropyl ether, toluene and hexane) enhanced the reaction rate drastically and gave optimal yields with high enantioselectivity (>99%). Moreover, enantiopure 3-hydroxy-3-phenylpropanenitrile products have been converted via enantioconvergent routes into the (R)- and (S)-enantiomers of the important anti-depressants fluoxetine, tomoxetine, nisoxetine and norfluoxetine

  （±）-3-羟基-3-苯基丙腈的简便制备方法是通过在乙醇水溶液中用NaCN开环氧化苯乙烯。随后通过脂肪酶介导的酯交换反应动力学分离该物质，得到S-醇和R-乙酸酯具有出色的收率和高对映选择性，尤其是对于脂肪酶PS-C'Amano'II而言。还研究了溶剂和脂肪酶固定化的作用。有趣的是，在疏水性溶剂（二异丙基醚，甲苯和己烷）的酯交换过程中使用固定化脂肪酶可大大提高反应速率，并以高对映选择性（> 99％）获得最佳收率。此外，对映体纯的3-羟基-3-苯基丙腈产物已通过对映收敛途径转化为重要的抗抑郁药氟西汀，托莫西汀，尼索西汀和去氟西汀的（R）-和（S）-对映体。
• Enzymatic method of making ethyl 3-hydroxy-3-phenylpropionate and their esters
  申请人：Hwang Soon Ook

  公开号：US20060205056A1

  公开（公告）日：2006-09-14

  The present invention provides a new process for the preparation of optically active ethyl 3-hydroxy-3-phenylpropionate and their esters by enzymatic method. More particularly, the racemic ethyl 3-hydroxy-3-phenylpropionate is converted to optically active ethyl 3-hydroxy-3-phenylpropionate and their esters by enzymatic reaction with acylating agent. This invention may be employed for the synthesis of individual enantiomers of ethyl 3-hydroxy-3-phenylpropionate.

  本发明提供了一种通过酶法制备光学活性乙酸乙酯3-羟基-3-苯基丙酸酯及其酯类的新工艺。更具体地说，通过酶催化反应与酰化剂反应，将外消旋乙酸乙酯3-羟基-3-苯基丙酸酯转化为光学活性乙酸乙酯3-羟基-3-苯基丙酸酯及其酯类。本发明可用于合成乙酸乙酯3-羟基-3-苯基丙酸酯的单一对映体。
• Thiacrown Ether Technology in Lipase-Catalyzed Reaction:  Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis
  作者：Toshiyuki Itoh、Koichi Mitsukura、Wipa Kanphai、Yumiko Takagi、Hiroshi Kihara、Hiroshi Tsukube

  DOI：10.1021/jo971288m

  日期：1997.12.1

  Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the-reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomethyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.
• A new facile chemoenzymatic synthesis of levamisole
  作者：Ahmed Kamal、G.B. Ramesh Khanna、T. Krishnaji、R. Ramu

  DOI：10.1016/j.bmcl.2004.11.054

  日期：2005.2

  An efficient and facile chemoenzymatic synthesis of levamisole by employing lipase-mediated resolution of 3-hydroxy-3-phenylpropanenitrile followed by its conversion to beta-amino alcohol as the key intermediate is described. (C) 2004 Elsevier Ltd. All rights reserved.