(Z)-3-(4-chlorophenyl)-2-cyanobut-2-enamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-3-(4-chlorophenyl)-2-cyanobut-2-enamide
• 英文别名: (2Z)-3-(4-chlorophenyl)-2-cyanobut-2-enamide
• 化学式: C₁₁H₉ClN₂O
• 分子量: 220.658
• InChiKey: JCGYRUPOGRPWKR-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氯苯乙酮 、 氰乙酰胺 在 吡啶 、 titanium(IV) isopropylate 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以95%的产率得到(Z)-3-(4-chlorophenyl)-2-cyanobut-2-enamide
  参考文献：
  名称：

  Titanium isopropoxide/pyridine mediated Knoevenagel reactions

  摘要：

  We report a Ti(OiPr)(4)/pyridine mediated Knoevenagel reaction between aromatic ketones and cyanoacetamides to provide Knoevenagel olefin products in good to excellent yields. Almost in all cases studied, a single geometrical isomer was formed and isolated under the Ti(OiPr)(4)/pyridine condensation conditions. This methodology was also demonstrated to be highly effective between some other Knoevenagel active methylene compounds and aromatic ketones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.069

文献信息

• Homogeneous and Stereoselective Copper(II)-Catalyzed Monohydration of Methylenemalononitriles to 2-Cyanoacrylamides
  作者：Xiaoqing Xin、Dexuan Xiang、Jiming Yang、Qian Zhang、Fenguo Zhou、Dewen Dong

  DOI：10.1021/jo401997v

  日期：2013.12.6

  A facile and efficient route for the homogeneous and highly stereoselective monohydration of substituted methylenemalononitriles to (E)-2-cyanoacrylamides catalyzed by copper(II) acetate monohydrate in acetic acid containing 2% water is described, and a mechanism is proposed. The protocol has proved to be suitable for the monohydration of dicyanobenzenes and 2-substituted malononitriles.
• Titanium isopropoxide/pyridine mediated Knoevenagel reactions
  作者：Brian A. Robichaud、Kevin G. Liu

  DOI：10.1016/j.tetlet.2011.10.069

  日期：2011.12

  We report a Ti(OiPr)(4)/pyridine mediated Knoevenagel reaction between aromatic ketones and cyanoacetamides to provide Knoevenagel olefin products in good to excellent yields. Almost in all cases studied, a single geometrical isomer was formed and isolated under the Ti(OiPr)(4)/pyridine condensation conditions. This methodology was also demonstrated to be highly effective between some other Knoevenagel active methylene compounds and aromatic ketones. (C) 2011 Elsevier Ltd. All rights reserved.