5-acetyl-6-methyl-4-(2-nitrophenyl)pyrimidin-2(1H)-one | 1091909-70-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-acetyl-6-methyl-4-(2-nitrophenyl)pyrimidin-2(1H)-one
• CAS: 1091909-70-4
• 化学式: C₁₃H₁₁N₃O₄
• 分子量: 273.248
• InChiKey: KRBSGXDCICNMSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  105.96
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  5-acetyl-6-methyl-3,4-dihydro-4-(2-nitrophenyl)pyrimidin-2(1H)-one 在 过氧化苯甲酰 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以60%的产率得到5-acetyl-6-methyl-4-(2-nitrophenyl)pyrimidin-2(1H)-one
  参考文献：
  名称：

  Free-radical oxidation of 1,2,3,4-tetrahydro-2-oxopyrimidines

  摘要：

  Free-radical oxidation of 4-substituted 5-acetyl- and 5-carboethoxy-1,2,3,4-tetrahydro-2-oxopyrimidines using benzoyl peroxide under thermal conditions has been investigated to elucidate the effects of the nature of the substituents in the 4- and 5-positions on the rate of reaction. Whereas the presence of the acetyl group instead of the carboethoxy group in position 5 decreases the rate of oxidation, the nature of the additional substituent (electron-releasing or electron-withdrawing group) and also its location on the phenyl ring attached to C-4 of the tetrahydropyrimidinone ring effectively influence the rate of reaction. The latter observation supports the proposal that the removal of the 4-hydrogen on the heterocyclic ring occurs in the rate-determining step.

  DOI：

  10.1007/s00706-011-0573-8