4-amino-1-(4-chloro-phenyl)-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile | 197805-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 4-amino-1-(4-chloro-phenyl)-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile
• 英文别名: 3-amino-1-(4-chlorophenyl)-5-oxo-2H-pyrrole-4-carbonitrile
• CAS: 197805-19-9
• 化学式: C₁₁H₈ClN₃O
• 分子量: 233.657
• InChiKey: APYPQUBHWNKUMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 4-amino-1-(4-chloro-phenyl)-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以87%的产率得到1-(4-chloro-phenyl)-2-oxo-4-pyrrolidin-1-yl-2,5-dihydro-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  New syntheses of 2,4-diaminopyrroles and aminopyrrolinones

  摘要：

  Oxazolin-2-ylidene-malononitriles 3a-d, obtainable from thioketenaminals and alpha-halogen-ketones, react with primary and secondary amines to afford 2,4-diamino-pyrroles 5a-h. Mercaptobenzen as nucleophilic agent gives the 4-amino-2-phenylthio-pyrrole 5j. Analogously, cyano-(3,5-diphenyl-3H-oxazol-2-ylidene)-acetic acid methyl esters were prepared as intermediates for the synthesis of 2-amino-4-oxo-pyrrolines 10a-d. The isomeric 4-amino-2-oxo-pyrrolines 13a-d can be obtained from 4-amino-2-methoxy-pyrroles, which serves as proof for the position of substituents. The structures were investigated by H-1 and C-13 NMR spectroscopy.

  DOI：

  10.1007/bf00807103
• 作为产物：
  描述：

  3-(4-chloro-anilino)-2-cyano-3-methylthio-acrylonitrile 在 吗啉 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 4-amino-1-(4-chloro-phenyl)-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  New syntheses of 2,4-diaminopyrroles and aminopyrrolinones

  摘要：

  Oxazolin-2-ylidene-malononitriles 3a-d, obtainable from thioketenaminals and alpha-halogen-ketones, react with primary and secondary amines to afford 2,4-diamino-pyrroles 5a-h. Mercaptobenzen as nucleophilic agent gives the 4-amino-2-phenylthio-pyrrole 5j. Analogously, cyano-(3,5-diphenyl-3H-oxazol-2-ylidene)-acetic acid methyl esters were prepared as intermediates for the synthesis of 2-amino-4-oxo-pyrrolines 10a-d. The isomeric 4-amino-2-oxo-pyrrolines 13a-d can be obtained from 4-amino-2-methoxy-pyrroles, which serves as proof for the position of substituents. The structures were investigated by H-1 and C-13 NMR spectroscopy.

  DOI：

  10.1007/bf00807103

文献信息

• New syntheses of 2,4-diaminopyrroles and aminopyrrolinones
  作者：M. Rehwald、H. Sch�fer、K. Gewald

  DOI：10.1007/bf00807103

  日期：——

  Oxazolin-2-ylidene-malononitriles 3a-d, obtainable from thioketenaminals and alpha-halogen-ketones, react with primary and secondary amines to afford 2,4-diamino-pyrroles 5a-h. Mercaptobenzen as nucleophilic agent gives the 4-amino-2-phenylthio-pyrrole 5j. Analogously, cyano-(3,5-diphenyl-3H-oxazol-2-ylidene)-acetic acid methyl esters were prepared as intermediates for the synthesis of 2-amino-4-oxo-pyrrolines 10a-d. The isomeric 4-amino-2-oxo-pyrrolines 13a-d can be obtained from 4-amino-2-methoxy-pyrroles, which serves as proof for the position of substituents. The structures were investigated by H-1 and C-13 NMR spectroscopy.