2-cyano-N-methyl-N,3-diphenylacrylamide | 247099-40-7

• 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: 2-cyano-N-methyl-N,3-diphenylacrylamide
• CAS: 247099-40-7
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: ZTKKXIFBBJAEDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.1
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-cyano-N-methyl-N,3-diphenylacrylamide 在 叔丁基过氧化氢 、 potassium fluoride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以885 mg的产率得到2-cyano-N-methyl-N,3-diphenyloxirane-2-carboxamide
  参考文献：
  名称：

  A Concise and Versatile Synthesis of Viridicatin Alkaloids from Cyanoacetanilides

  摘要：

  The efficient synthesis of 3-hydroxy-4-arylquinolin-2(1H)-ones through one-pot Knoevenagel condensation/epoxidation of cyanoacetanilides followed by decyanative epoxide-arene cyclization is described. A convergent assembly with functionalized aldehydes allows for rapid synthesis with diverse substitution patterns. Isolation of 3-hydroxy-4-arylquinolin-2(1H)-ones is readily accomplished by precipitation and filtration.

  DOI：

  10.1021/ol900255g
• 作为产物：
  描述：

  3-(N-甲基-N-苯基氨基)-3-氧代丙腈 、 苯甲醛 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 2-cyano-N-methyl-N,3-diphenylacrylamide
  参考文献：
  名称：

  A Concise and Versatile Synthesis of Viridicatin Alkaloids from Cyanoacetanilides

  摘要：

  The efficient synthesis of 3-hydroxy-4-arylquinolin-2(1H)-ones through one-pot Knoevenagel condensation/epoxidation of cyanoacetanilides followed by decyanative epoxide-arene cyclization is described. A convergent assembly with functionalized aldehydes allows for rapid synthesis with diverse substitution patterns. Isolation of 3-hydroxy-4-arylquinolin-2(1H)-ones is readily accomplished by precipitation and filtration.

  DOI：

  10.1021/ol900255g

文献信息

• Iron-catalyzed carbonylation–arylation of N-arylacrylamides for synthesis of oxindole derivatives
  作者：Fan Jia、Kaisheng Liu、Hui Xi、Shenglin Lu、Zhiping Li

  DOI：10.1016/j.tetlet.2013.09.048

  日期：2013.11

  An efficient method for oxindole synthesis is established by iron-catalyzed carbonylation-arylation of N-arylacrylamides with aldehydes. 3-Functionalized oxindoles are synthesized smoothly using FeCl3 as catalyst and TBHP as oxidant. The obtained oxindoles can be used for further transformations to give diverse indole alkaloid structure motifs. (C) 2013 Elsevier Ltd. All rights reserved.