4-amino-5-benzoyl-1-phenyl-pyrrol-3-carbonitril | 59021-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-5-benzoyl-1-phenyl-pyrrol-3-carbonitril
• 英文别名: 4-Amino-5-benzoyl-1-phenylpyrrole-3-carbonitrile
• CAS: 59021-49-7
• 化学式: C₁₈H₁₃N₃O
• 分子量: 287.321
• InChiKey: RKZYICQDXUZGNP-UHFFFAOYSA-N

物化性质

• 沸点：
  542.3±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-[(N-phenacylanilino)methylidene]propanedinitrile 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以64%的产率得到4-amino-5-benzoyl-1-phenyl-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

文献信息

• Synthetis of Pyrrole, and Andpyridinone Pyrimidinone Derivatives Using PTC Conditions
  作者：H. Abdel-Ghany、A. M. El-Sayed、A. K. El-Shafei

  DOI：10.1080/00397919508012676

  日期：1995.4

  The reaction of anilinomethylenemalononitrile 1 or 1,4-di(malononitrilemethyleneamino)benzene 7 with some reactive halo compounds in a one-pot reaction under PTC conditions affords a new series of pyrrole and pyridinone compounds. The reaction of compounds 1 or 7 with ethyl chloroformate gives the corresponding esters which underwent cyclization on reaction with different amino compounds affording the pyrimidinone derivatives.