(E)-2-cyano-3-phenylbut-2-enamide | 25327-42-8

• 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: (E)-2-cyano-3-phenylbut-2-enamide
• 英文别名: 2-Cyano-3-phenylbut-2-enamide
• CAS: 25327-42-8
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: BCUZMFYXVADHLQ-CSKARUKUSA-N

物化性质

• 沸点：
  389.8±42.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  (E)-2-cyano-3-phenylbut-2-enamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  Marecki, Paul E.; Wemple, James N.; Butke, Gregory P., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1247 - 1248

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(1-苯基亚乙基)丙二腈 在 copper(II) acetate monohydrate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 12.0h， 以33.333%的产率得到
  参考文献：
  名称：

  Homogeneous and Stereoselective Copper(II)-Catalyzed Monohydration of Methylenemalononitriles to 2-Cyanoacrylamides

  摘要：

  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.

  DOI：

  10.1021/jo401997v

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.
• Armesto, Diego; Albert, Armando; Cano, Felix H., Journal of the Chemical Society. Perkin transactions I, 1997, # 22, p. 3401 - 3405
  作者：Armesto, Diego、Albert, Armando、Cano, Felix H.、Martin, Nazario、Ramos, Ana、Rodriguez, Miriam、Segura, Jose L.、Seoane, Carlos

  DOI：——

  日期：——
• Elagamey, Abdel-Ghani Ali, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 766 - 768
  作者：Elagamey, Abdel-Ghani Ali

  DOI：——

  日期：——
• ELAGAMEY, ABDEL-GHANI ALI, INDIAN J. CHEM. B, 27,(1988) N, C. 766-768
  作者：ELAGAMEY, ABDEL-GHANI ALI

  DOI：——

  日期：——
• MARECKI, P. E.;WEMPLE, J. N.;BUTKE, G. P., J. HETEROCYCL. CHEM., 1982, 19, N 5, 1247-1248
  作者：MARECKI, P. E.、WEMPLE, J. N.、BUTKE, G. P.

  DOI：——

  日期：——