(Z)-2-cyano-3-phenylbut-2-enamide | 25327-41-7

• 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)-2-cyano-3-phenylbut-2-enamide
• 英文别名: α-Cyan-β-methyl-cis-zimtsaeureamid；seqcis-2-Cyano-3-methyl-3-phenyl-acrylsaeureamid；cis-2-Cyan-3-phenyl-croton-saeureamid；(2Z)-2-cyano-3-phenylbut-2-enamide
• CAS: 25327-41-7
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: BCUZMFYXVADHLQ-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 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：

  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93%的产率得到(Z)-2-cyano-3-phenylbut-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

• Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases
  作者：Christoph Nitsche、Christian Steuer、Christian D. Klein

  DOI：10.1016/j.bmc.2011.10.061

  日期：2011.12

  The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a K(i)-value of 35.7 mu M at the Dengue and 44.6 mu M at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.