2-{[Methyl-(2-oxo-2-phenyl-ethyl)-amino]-methylene}-malononitrile | 145162-26-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-{[Methyl-(2-oxo-2-phenyl-ethyl)-amino]-methylene}-malononitrile
• 英文别名: 2-[[Methyl(phenacyl)amino]methylidene]propanedinitrile
• CAS: 145162-26-1
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: BJJBQWCMDNRAQP-UHFFFAOYSA-N

物化性质

• 沸点：
  543.7±40.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{[Methyl-(2-oxo-2-phenyl-ethyl)-amino]-methylene}-malononitrile 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以58%的产率得到4-amino-5-benzoyl-1-methyl-pyrrol-3-carbonitril
  参考文献：
  名称：

  Zur Synthese von 3-Amino-pyrrolen durch Thorpe-Ziegler-Cyclisierung

  摘要：

  N-Aryl and alkylaminomethylene cyanacetic acid derivatives 1 react with alpha-halogencarbonyl compounds 2 in the presence of potassium carbonate/sodium ethoxide to yield the substituted 3-amino-pyrroles 6. Using the same principle of cyclization pyrrole derivatives 6 can also be obtained by reaction of beta-chloro- and beta-alkoxymethylenemalononitriles 4 with beta-aminocarbonyl compounds 5. From the malononitrile derivatives 1 containing the methylthio group in the beta-position, and alpha-halogen ketones 7, the 2-dicyanomethylene oxazolines 8 arise which undergo alkoholysis by treatment with sodium alkoxide to form the 3-amino-5-alkoxy-pyrrole derivatives 9.

  DOI：

  10.1002/prac.19923340608
• 作为产物：
  描述：

  2-((methylamino)methylene)malononitrile 、 2-溴苯乙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到2-{[Methyl-(2-oxo-2-phenyl-ethyl)-amino]-methylene}-malononitrile
  参考文献：
  名称：

  Zur Synthese von 3-Amino-pyrrolen durch Thorpe-Ziegler-Cyclisierung

  摘要：

  N-Aryl and alkylaminomethylene cyanacetic acid derivatives 1 react with alpha-halogencarbonyl compounds 2 in the presence of potassium carbonate/sodium ethoxide to yield the substituted 3-amino-pyrroles 6. Using the same principle of cyclization pyrrole derivatives 6 can also be obtained by reaction of beta-chloro- and beta-alkoxymethylenemalononitriles 4 with beta-aminocarbonyl compounds 5. From the malononitrile derivatives 1 containing the methylthio group in the beta-position, and alpha-halogen ketones 7, the 2-dicyanomethylene oxazolines 8 arise which undergo alkoholysis by treatment with sodium alkoxide to form the 3-amino-5-alkoxy-pyrrole derivatives 9.

  DOI：

  10.1002/prac.19923340608