3-cyano-5-formyl-4-(4-methylphenylamino)-2-oxo-1,2-dihydropyridine | 836607-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-cyano-5-formyl-4-(4-methylphenylamino)-2-oxo-1,2-dihydropyridine
• 英文别名: 5-formyl-4-(4-methylanilino)-2-oxo-1H-pyridine-3-carbonitrile
• CAS: 836607-16-0
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: DRZIBUAHDSCIKH-UHFFFAOYSA-N

物化性质

• 熔点：
  304-306 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  373.7±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  82
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-cyano-5-formyl-4-(4-methylphenylamino)-2-oxo-1,2-dihydropyridine 在 三乙胺盐酸盐 、 三氯氧磷 作用下， 反应 1.0h， 以50%的产率得到3-chloro-4-cyano-8-methylbenzo[b][1,6]naphthyridine
  参考文献：
  名称：

  Synthesis and hydrolytic cleavage of 1-aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo(thioxo)-1,4-dihydropyrimidines

  摘要：

  1-Aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo-1,4-dihydropyrimidines and their 4-thioxo analogs, which were prepared in three steps from cyanoacetamide and cyanothioacetamide, respectively, were subjected to hydrolysis. In aqueous AcOH, hydrolysis of N-(dimethylaminomethylene)-2-cyano-5-dimethylamino-2,4-pentadieneamide derivatives containing amino groups at position 3 afforded formylpyridones. The reaction of 2-cyano-3-dimethylaminothiocrotonamide with DMF dimethyl acetal gave rise to 3-cyano-4-dimethylamino-2-methylthiopyridine.

  DOI：

  10.1023/b:rucb.0000037857.07190.75
• 作为产物：
  描述：

  α-cyano-β-dimethylaminocrotonamide 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 3-cyano-5-formyl-4-(4-methylphenylamino)-2-oxo-1,2-dihydropyridine
  参考文献：
  名称：

  Synthesis and hydrolytic cleavage of 1-aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo(thioxo)-1,4-dihydropyrimidines

  摘要：

  1-Aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo-1,4-dihydropyrimidines and their 4-thioxo analogs, which were prepared in three steps from cyanoacetamide and cyanothioacetamide, respectively, were subjected to hydrolysis. In aqueous AcOH, hydrolysis of N-(dimethylaminomethylene)-2-cyano-5-dimethylamino-2,4-pentadieneamide derivatives containing amino groups at position 3 afforded formylpyridones. The reaction of 2-cyano-3-dimethylaminothiocrotonamide with DMF dimethyl acetal gave rise to 3-cyano-4-dimethylamino-2-methylthiopyridine.

  DOI：

  10.1023/b:rucb.0000037857.07190.75

文献信息

• Synthesis and hydrolytic cleavage of 1-aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo(thioxo)-1,4-dihydropyrimidines
  作者：A. S. Ivanov、N. Z. Tugusheva、L. M. Alekseeva、V. G. Granik

  DOI：10.1023/b:rucb.0000037857.07190.75

  日期：2004.4

  1-Aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo-1,4-dihydropyrimidines and their 4-thioxo analogs, which were prepared in three steps from cyanoacetamide and cyanothioacetamide, respectively, were subjected to hydrolysis. In aqueous AcOH, hydrolysis of N-(dimethylaminomethylene)-2-cyano-5-dimethylamino-2,4-pentadieneamide derivatives containing amino groups at position 3 afforded formylpyridones. The reaction of 2-cyano-3-dimethylaminothiocrotonamide with DMF dimethyl acetal gave rise to 3-cyano-4-dimethylamino-2-methylthiopyridine.