1-amino-5-(N-phenylamino)-1-phenylhexa-1,4-dien-3-one | 143889-62-7

• 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: 1-amino-5-(N-phenylamino)-1-phenylhexa-1,4-dien-3-one
• 英文别名: (1Z,4Z)-1-amino-5-anilino-1-phenylhexa-1,4-dien-3-one
• CAS: 143889-62-7
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: QSKMFKIFJKELBN-REFMDLPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-amino-5-(N-phenylamino)-1-phenylhexa-1,4-dien-3-one 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 2-甲基-6-苯基-4(1h)-吡啶酮
  参考文献：
  名称：

  Reaction of dianions of acyclic .beta.-enamino ketones with electrophiles. 3. Nitriles: synthesis of pyridine and pyrimidine derivatives

  摘要：

  A new method for the construction of pyridine and pyrimidine derivatives is described, based on the electrophilic attack of nitriles to dianions of beta-(monoalkylamino)-alpha,beta-unsaturated ketones and the subsequent cyclization of the addition product. The reaction proceeds in good to high yields with both alpha'- and gamma-dianions which are regioselectively generated. The reaction of gamma-dianions with nitriles is strongly influenced by temperature. The gamma-addition products cyclize to 4-aminopyridines when the reaction is run below -50-degrees-C. From reactions performed over 0-degrees-C pyrimidines arising from addition of 2 mol of nitriles are isolated. Owing to the polar conditions employed, a side metalation reaction is observed with aliphatic nitriles. On the other hand, the alpha'-addition products can be isolated in neutral conditions but they cyclize to 4-pyridinones in strong acidic media.

  DOI：

  10.1021/jo00048a043
• 作为产物：
  描述：

  4-苯基氨基-3-戊烯-2-酮 、 苯甲腈 生成 1-amino-5-(N-phenylamino)-1-phenylhexa-1,4-dien-3-one
  参考文献：
  名称：

  Reaction of dianions of acyclic .beta.-enamino ketones with electrophiles. 3. Nitriles: synthesis of pyridine and pyrimidine derivatives

  摘要：

  A new method for the construction of pyridine and pyrimidine derivatives is described, based on the electrophilic attack of nitriles to dianions of beta-(monoalkylamino)-alpha,beta-unsaturated ketones and the subsequent cyclization of the addition product. The reaction proceeds in good to high yields with both alpha'- and gamma-dianions which are regioselectively generated. The reaction of gamma-dianions with nitriles is strongly influenced by temperature. The gamma-addition products cyclize to 4-aminopyridines when the reaction is run below -50-degrees-C. From reactions performed over 0-degrees-C pyrimidines arising from addition of 2 mol of nitriles are isolated. Owing to the polar conditions employed, a side metalation reaction is observed with aliphatic nitriles. On the other hand, the alpha'-addition products can be isolated in neutral conditions but they cyclize to 4-pyridinones in strong acidic media.

  DOI：

  10.1021/jo00048a043

文献信息

• Reaction of dianions of acyclic .beta.-enamino ketones with electrophiles. 3. Nitriles: synthesis of pyridine and pyrimidine derivatives
  作者：Giuseppe Bartoli、Marcella Bosco、Cristina Cimarelli、Renato Dalpozzo、Giovanni De Munno、Giuseppe Guercio、Gianni Palmieri

  DOI：10.1021/jo00048a043

  日期：1992.10

  A new method for the construction of pyridine and pyrimidine derivatives is described, based on the electrophilic attack of nitriles to dianions of beta-(monoalkylamino)-alpha,beta-unsaturated ketones and the subsequent cyclization of the addition product. The reaction proceeds in good to high yields with both alpha'- and gamma-dianions which are regioselectively generated. The reaction of gamma-dianions with nitriles is strongly influenced by temperature. The gamma-addition products cyclize to 4-aminopyridines when the reaction is run below -50-degrees-C. From reactions performed over 0-degrees-C pyrimidines arising from addition of 2 mol of nitriles are isolated. Owing to the polar conditions employed, a side metalation reaction is observed with aliphatic nitriles. On the other hand, the alpha'-addition products can be isolated in neutral conditions but they cyclize to 4-pyridinones in strong acidic media.