6-Bromo-1,3-dimethyl-1,5,5a,6,7,8,9,9a-octahydro-pyrimido[5,4-b]indole-2,4-dione | 360559-79-1

• 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: 6-Bromo-1,3-dimethyl-1,5,5a,6,7,8,9,9a-octahydro-pyrimido[5,4-b]indole-2,4-dione
• 英文别名: 6-bromo-1,3-dimethyl-5a,6,7,8,9,9a-hexahydro-5H-pyrimido[5,4-b]indole-2,4-dione
• CAS: 360559-79-1
• 化学式: C₁₂H₁₆BrN₃O₂
• 分子量: 314.182
• InChiKey: PRWFSWURPVGBQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  56.03
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-Bromo-1,3-dimethyl-1,5,5a,6,7,8,9,9a-octahydro-pyrimido[5,4-b]indole-2,4-dione 在 palladium on activated charcoal 作用下， 以 二苯醚 为溶剂， 反应 0.5h， 以91%的产率得到1,3-dimethyl-5H-indolo[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Studies on Pyrimidines: Synthesis of Pyrimidine-Annelated Heterocycles from 5-Amino-6-cyclohex-2-enyl-1, 3-dimethyl-uracil

  摘要：

  Treatment of 5-amino-6-cyclohex-2-enyl-1,3-dimethyl-uracil with pyridinium hydrotribromide or hexamethylenetetrammonium hydrotribromide furnished the corresponding linear heterocyclic 6-bromo-1,3-dimethylhexahydroindolo[3,2-d]pyrimidine-2,4-diones in 90% yield. Reaction of the same educt with molecular bromine in chloroform afforded the bicyclic 9-bromo-1,3-dimethylhexahydrobicyclo [3.3.1]indole[3,2-d]pyrimidine-2,4-diones in 85% yield. Upon treatment of the above substrate with cold concentrated sulfuric acid, a mixture of 1,3-dimethylhexahydroindolo[3,2-d]pyrimidine-2,4-dione (28%) and 1,3-dimethylhexahydrobicyclo [3.3.1]indolo[3,2-d]pyrimidine-2,4-dione (60%) was obtained.

  DOI：

  10.1007/s007060170100
• 作为产物：
  描述：

  5-(N-(cyclohex-2-enyl)-N-methylamino)-1,3-dimethyluracil 在 盐酸 、 pyridinium hydrobromide perbromide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 6-Bromo-1,3-dimethyl-1,5,5a,6,7,8,9,9a-octahydro-pyrimido[5,4-b]indole-2,4-dione
  参考文献：
  名称：

  Studies on Pyrimidines: Synthesis of Pyrimidine-Annelated Heterocycles from 5-Amino-6-cyclohex-2-enyl-1, 3-dimethyl-uracil

  摘要：

  Treatment of 5-amino-6-cyclohex-2-enyl-1,3-dimethyl-uracil with pyridinium hydrotribromide or hexamethylenetetrammonium hydrotribromide furnished the corresponding linear heterocyclic 6-bromo-1,3-dimethylhexahydroindolo[3,2-d]pyrimidine-2,4-diones in 90% yield. Reaction of the same educt with molecular bromine in chloroform afforded the bicyclic 9-bromo-1,3-dimethylhexahydrobicyclo [3.3.1]indole[3,2-d]pyrimidine-2,4-diones in 85% yield. Upon treatment of the above substrate with cold concentrated sulfuric acid, a mixture of 1,3-dimethylhexahydroindolo[3,2-d]pyrimidine-2,4-dione (28%) and 1,3-dimethylhexahydrobicyclo [3.3.1]indolo[3,2-d]pyrimidine-2,4-dione (60%) was obtained.

  DOI：

  10.1007/s007060170100