diethyl 4,4'-(1,4-phenylene)bis[6-(chloromethyl)-1,2,3,4-tetrahydro-1-methyl-2-oxopyrimidine-5-carboxylate] | 1246405-35-5

• 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: diethyl 4,4'-(1,4-phenylene)bis[6-(chloromethyl)-1,2,3,4-tetrahydro-1-methyl-2-oxopyrimidine-5-carboxylate]
• 英文别名: ethyl 4-(chloromethyl)-6-[4-[4-(chloromethyl)-5-ethoxycarbonyl-3-methyl-2-oxo-1,6-dihydropyrimidin-6-yl]phenyl]-3-methyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
• CAS: 1246405-35-5
• 化学式: C₂₄H₂₈Cl₂N₄O₆
• 分子量: 539.416
• InChiKey: LRKYRBFNDZMTES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 4,4'-(1,4-phenylene)bis[6-(chloromethyl)-1,2,3,4-tetrahydro-1-methyl-2-oxopyrimidine-5-carboxylate] 、 C.I.酸性橙108 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 4.0h， 以24%的产率得到4,4'-(1,4-phenylene)bis(3,4,6,7-tetrahydro-6-(2-hydroxyethyl)-1-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,5-dione)
  参考文献：
  名称：

  One-pot synthesis of diethyl 4,4′-(1,4-phenylene)bis[6-(halomethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] and their bispyrrolocyclization

  摘要：

  A one-pot synthesis of diethyl 4,4'-(1,4-phenylene)bis[6-(chloromethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] is proposed via three-component condensation of terephthalic aldehyde, 4-chloroacetoacetic ester, and ureas under Biginelli reaction conditions. Interaction of the obtained precursors that contain two highly reactive binucleophilic groups with primary amines leads to bis-heterocyclization with formation of (1,4-phenylene)bis(pyrrolo[3,4-d]pyrimidine-2,5-diones).

  DOI：

  10.1007/s00706-010-0354-9
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 、 对苯二甲醛 、 N-甲基脲 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以55%的产率得到diethyl 4,4'-(1,4-phenylene)bis[6-(chloromethyl)-1,2,3,4-tetrahydro-1-methyl-2-oxopyrimidine-5-carboxylate]
  参考文献：
  名称：

  One-pot synthesis of diethyl 4,4′-(1,4-phenylene)bis[6-(halomethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] and their bispyrrolocyclization

  摘要：

  A one-pot synthesis of diethyl 4,4'-(1,4-phenylene)bis[6-(chloromethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] is proposed via three-component condensation of terephthalic aldehyde, 4-chloroacetoacetic ester, and ureas under Biginelli reaction conditions. Interaction of the obtained precursors that contain two highly reactive binucleophilic groups with primary amines leads to bis-heterocyclization with formation of (1,4-phenylene)bis(pyrrolo[3,4-d]pyrimidine-2,5-diones).

  DOI：

  10.1007/s00706-010-0354-9