(1-氰基-3-苯基丙-2-烯基)乙酸酯 | 79265-03-5

• 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: (1-氰基-3-苯基丙-2-烯基)乙酸酯
• 英文名称: Acetic acid (E)-1-cyano-3-phenyl-allyl ester
• 英文别名: 1-Cyano-3-phenylprop-2-en-1-yl acetate；(1-cyano-3-phenylprop-2-enyl) acetate
• CAS: 79265-03-5
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: RFWLNUBUIPCBII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (1-氰基-3-苯基丙-2-烯基)乙酸酯 在 四(三苯基膦)钯 、 三正丁基氢锡 、 氯化铵 、 1,3-丙二醇 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 4-phenylbut-3-enenitrile
  参考文献：
  名称：

  Organo tin nucleophiles iii. Palladium catalyzed reductive cleavage of allylic heterosubstituents with tin hydride

  摘要：

  DOI：

  10.1016/s0040-4039(00)86797-0
• 作为产物：
  描述：

  肉桂醛 在 吡啶 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 (1-氰基-3-苯基丙-2-烯基)乙酸酯
  参考文献：
  名称：

  Fast Microwave-Assisted Resolution of (±)-Cyanohydrins Promoted by Lipase fromCandida antarctica

  摘要：

  Enzymatic kinetic resolution (EKR) of (+/-)-cyanohydrins was performed by using immobilized lipase from Candida antarctica (CALB) under conventional ordinary conditions (orbital shaking) and under microwave radiation (MW). The use of microwave radiation contributed very expressively on the reduction of the reaction time from 24 to 2 h. Most importantly, high selectivity (up to 92% ee(p)) as well as conversion was achieved under MW radiation (50-56%).

  DOI：

  10.5935/0103-5053.20150102

文献信息

• Zinc Tetrafluoroborate-Catalyzed Efficient Conversion of Aldehydes to Geminal Diacetates and Cyanoacetates
  作者：Brindaban C. Ranu、Jyotirmoy Dutta、Arijit Das

  DOI：10.1246/cl.2003.366

  日期：2003.4

  A trace of an aqueous solution of zinc tetrafluoroborate was demonstrated to catalyze the conversion of an aldehyde to its 1,1-diacetate by acetic anhydride without any solvent. A similar reaction of an aldehyde with a mixture of potassium cyanide and acetic anhydride in methylene chloride was also catalyzed by Zn(BF4)2 to provide the corresponding geminal cyanoacetate.

  演示了一种含锌四氟硼酸盐的水溶液在无任何溶剂的情况下催化醛向其1,1-二乙酸酯的转化，该转化是通过乙酸酐实现的。类似地，在二氯甲烷中，醛与氰化钾和乙酸酐的混合反应也受到Zn(BF₄)₂的催化，生成相应的乙二酸酯。
• TBD- or PS-TBD-Catalyzed One-Pot Synthesis of Cyanohydrin Carbonates and Cyanohydrin Acetates from Carbonyl Compounds
  作者：Satoru Matsukawa、Junya Kimura、Miki Yoshioka

  DOI：10.3390/molecules21081030

  日期：——

  Cyanation reactions of carbonyl compounds with methyl cyanoformate or acetyl cyanide catalyzed by 5 mol % of 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) were examined. Using methyl cyanoformate, the corresponding cyanohydrin carbonates were readily obtained in high yield for aromatic and aliphatic aldehydes and ketones. Similar results were obtained when acetyl cyanide was used as the cyanide source.

  考察了羰基化合物与氰基甲酸甲酯或乙酰氰化物在5 mol％的1,5,7-三氮杂双环[4,4,0] dec-5-ene（TBD）催化下的氰化反应。使用氰基甲酸甲酯，可以以高收率容易地获得相应的氰基碳酸酯，以用于芳族和脂族醛和酮。当使用乙酰氰作为氰化物源时，获得了相似的结果。聚合物负载的催化剂PS-TBD也是该反应的良好催化剂。PS-TBD易于回收并可以以最小的活动损失重新使用。
• IMPROVED THREE-COMPONENT LEWIS ACID-FREE APPROACH FOR THE SYNTHESIS OF PROTECTED RACEMIC CYANOHYDRINS
  作者：G. Kumaraswamy、K. Ankamma

  DOI：10.1080/00304940809458105

  日期：2008.10
• Catalytic, asymmetric synthesis of α-acetoxy amides
  作者：Michael North、Adrian W. Parkins、Atiya N. Shariff

  DOI：10.1016/j.tetlet.2004.08.114

  日期：2004.10

  Non-racemic cyanohydrin acetates are readily available from aldehydes and potassium cyanide/acetic anhydride by use of bimetallic titanium (salen) catalyst 1. Treatment of the cyanohydrin acetates with a platinum(II) phosphinito catalyst 3 under neutral conditions results in chemoselective hydrolysis to the corresponding alpha-acetoxy amides in a racemization free process. (C) 2004 Elsevier Ltd. All rights reserved.
• Nudelman, Abraham; Keinan, Ehud, Synthesis, 1982, # 8, p. 687 - 688
  作者：Nudelman, Abraham、Keinan, Ehud

  DOI：——

  日期：——