4-amino-5-methyl-3-phenyl-5-p-tolyl-1H-pyrrol-2(5H)-one | 1381802-85-2

• 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-5-methyl-3-phenyl-5-p-tolyl-1H-pyrrol-2(5H)-one
• 英文别名: 4-amino-5-methyl-5-(4-methylphenyl)-3-phenyl-1H-pyrrol-2-one
• CAS: 1381802-85-2
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: ZSAMBADAGCVZRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-[1-cyano-1-(4-methylphenyl)ethyl]-2-phenylacetamide 在 potassium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以76%的产率得到4-amino-5-methyl-3-phenyl-5-p-tolyl-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  Approaches to the Construction of Substituted 4-Amino-1H-pyrrol-2(5H)-ones

  摘要：

  Fully substituted 4-aminopyrrolones are easily accessed via simple routes starting from imines, ketones, or alpha-bromophenyl acetonitriles. Imines were reacted with KCN/NH4Cl in aqueous ethanol to produce alpha-arylamino benzyl cyanides. On the other hand, ketones were transformed to the desired alpha-amino nitriles using a modified Strecker reaction. Then, alpha-amino nitrile precursors were allowed to react with a suitable acyl halide to produce the corresponding amides. Further treatment of these amides with ethanolic KOH converted them to highly substituted 4-amino-1H-pyrrol-2(5H)-one derivatives in moderate to excellent yields.

  DOI：

  10.1021/jo3004309

文献信息

• Approaches to the Construction of Substituted 4-Amino-1<i>H</i>-pyrrol-2(5<i>H</i>)-ones
  作者：Hassan Zali-Boeini、Mehdi Mobin、Khadijeh Hajibabaei、Maryam Ghani

  DOI：10.1021/jo3004309

  日期：2012.7.6

  Fully substituted 4-aminopyrrolones are easily accessed via simple routes starting from imines, ketones, or alpha-bromophenyl acetonitriles. Imines were reacted with KCN/NH4Cl in aqueous ethanol to produce alpha-arylamino benzyl cyanides. On the other hand, ketones were transformed to the desired alpha-amino nitriles using a modified Strecker reaction. Then, alpha-amino nitrile precursors were allowed to react with a suitable acyl halide to produce the corresponding amides. Further treatment of these amides with ethanolic KOH converted them to highly substituted 4-amino-1H-pyrrol-2(5H)-one derivatives in moderate to excellent yields.