Ethyl 2-cyano-4-phenylbut-2-enoate | 525569-24-8

• 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: Ethyl 2-cyano-4-phenylbut-2-enoate
• CAS: 525569-24-8
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: NIAQFDFUIIQKFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙醛 、 氰乙酸乙酯 在 PS-PyCl-XAlCl₃ 作用下， 以 乙醇 为溶剂， 反应 1.3h， 以90%的产率得到Ethyl 2-cyano-4-phenylbut-2-enoate
  参考文献：
  名称：

  Polystyrene-Supported Pyridinium Chloroaluminate Ionic Liquid as a New Heterogeneous Lewis Acid Catalyst for Knoevenagel Condensation

  摘要：

  先将 Merrifield 树脂与吡啶反应，然后与氯化铝反应，制备出了非吸湿性聚苯乙烯支撑的氯铝酸盐离子液体。这种路易斯酸性离子液体是一种环境友好型异相催化剂，可用于芳香族和脂肪族醛与氰乙酸乙酯的克诺文纳格尔缩合反应。该催化剂非常稳定（作为台式催化剂），易于回收和重复使用，其效率不会有明显变化。

  DOI：

  10.3184/174751912x13377118207526

文献信息

• One methyl group makes a major difference: shape-selective catalysis by zeolite nanoreactors in liquid-phase condensation reactions
  作者：Chang Liu、Changyan Cao、Jian Liu、Xiaoshi Wang、Yanan Zhu、Weiguo Song

  DOI：10.1039/c7ta04187j

  日期：——

  Shape-selectivity with one-methyl-group-precision can be realized in Knoevenagel condensation reactions on zeolite crystals encapsulating basic active sites.

  在包裹基本活性位点的沸石晶体上，可以实现具有一个甲基精度的形状选择性Knoevenagel缩合反应。
• Polystyrene-Supported Pyridinium Chloroaluminate Ionic Liquid as a New Heterogeneous Lewis Acid Catalyst for Knoevenagel Condensation
  作者：Kaveh Parvanak Boroujeni、Mina Jafarinasab

  DOI：10.3184/174751912x13377118207526

  日期：2012.7

  Non-hygroscopic polystyrene-supported chloroaluminate ionic liquid was prepared from the reaction of Merrifield resin with pyridine followed by reaction with aluminium chloride. This Lewis acidic ionic liquid is an environmentally friendly heterogeneous catalyst for the Knoevenagel condensation of aromatic and aliphatic aldehydes with ethyl cyanoacetate. The catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency.

  先将 Merrifield 树脂与吡啶反应，然后与氯化铝反应，制备出了非吸湿性聚苯乙烯支撑的氯铝酸盐离子液体。这种路易斯酸性离子液体是一种环境友好型异相催化剂，可用于芳香族和脂肪族醛与氰乙酸乙酯的克诺文纳格尔缩合反应。该催化剂非常稳定（作为台式催化剂），易于回收和重复使用，其效率不会有明显变化。
• Polystyrene-supported chloroaluminate ionic liquid as a new heterogeneous Lewis acid catalyst for Knoevenagel condensation
  作者：Kaveh Parvanak Boroujeni、Mina Jafarinasab

  DOI：10.1016/j.cclet.2012.06.019

  日期：2012.9

  Non-hygroscopic polystyrene-supported chloroaluminate ionic liquid was prepared from the reaction of Merrifield resin with 1-methylimidazole followed by reaction with aluminum chloride. This Lewis acidic ionic liquid is environmentally friendly heterogeneous catalyst for the Knoevenagel condensation of aromatic and aliphatic aldehydes with ethyl cyanoacetate. The catalyst is stable (as a bench top catalyst) and reusable. (C) 2012 Kaveh Parvanak Boroujeni. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• The Knoevenagel condensation using quinine as an organocatalyst under solvent-free conditions
  作者：Kavita Jain、Saikat Chaudhuri、Kuntal Pal、Kalpataru Das

  DOI：10.1039/c8nj04219e

  日期：——

  organocatalyst to afford various electrophilic alkenes in excellent yields (up to 90%). In the presence of a catalytic amount of quinine (15 mol%), the reaction proceeded at room temperature (RT) under solvent-free conditions. In this green approach, the organocatalyst was recovered and recycled for up to four cycles without appreciable loss of activity.

  使用奎宁作为有机催化剂，可以开发出活性亚甲基化合物与芳族羰基化合物之间的Knoevenagel缩合反应，从而以极高的收率（最高90％）提供各种亲电子烯烃。在催化量的奎宁（15mol％）的存在下，反应在室温（RT）下在无溶剂条件下进行。在这种绿色方法中，有机催化剂被回收并循环使用多达四个周期，而活性没有明显下降。