1,3,8,8-tetramethyl-3,8-dihydro-purine-2,6-dione | 715-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1,3,8,8-tetramethyl-3,8-dihydro-purine-2,6-dione
• 英文别名: Xanthine, 1,3,8,8-tetramethyl-；1,3,8,8-tetramethylpurine-2,6-dione
• CAS: 715-59-3
• 化学式: C₉H₁₂N₄O₂
• 分子量: 208.22
• InChiKey: JMTLMQWWWBRZLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  65.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-isopropylamino-1,3-dimethyl-1H-pyrimidine-2,4-dione 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 偶氮二异丁腈 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,3,8,8-tetramethyl-3,8-dihydro-purine-2,6-dione
  参考文献：
  名称：

  A High Chemical Reactivity of 5-Azidouracils and Its Synthetic Application: Novel Synthesis of 8-Substituted 1,3-Dimethylxanthine Derivatives

  摘要：

  A novel method for the preparation of 8-substituted 1,3-dimethylxanthine derivatives (7 or 8) is described: treatment of 6-alkylamino-5-bromo-1,3-dimethyluracils (6a-e), easily prepared by bromination of the corresponding 6-alkylamino-1, 3-dimethyluracils (5), with sodium azide in DMF at ambient temperature allowed the direct formation of the 8-substituted 1,3-dimethylxanthines (7) proceeding via a transient formation of the corresponding 5-azido-1 ,3-dimethyluracils. The 5-bromo-1,3-dimethyluracils (6f, g) possessing an ct-branched alkylamino group at the 6-position similarly react with sodium azide to afford 8,8-disubstituted 1,3-dimethyl-8H-xanthines (8,8-disubstituted 1,3-dimethyl-3,g-dihydropurine-2,6-diones)(8).

  DOI：

  10.3987/com-97-s68

文献信息

• A High Chemical Reactivity of 5-Azidouracils and Its Synthetic Application: Novel Synthesis of 8-Substituted 1,3-Dimethylxanthine Derivatives
  作者：Kosaku Hirota、Magoichi Sako、Hironao Sajiki

  DOI：10.3987/com-97-s68

  日期：——

  A novel method for the preparation of 8-substituted 1,3-dimethylxanthine derivatives (7 or 8) is described: treatment of 6-alkylamino-5-bromo-1,3-dimethyluracils (6a-e), easily prepared by bromination of the corresponding 6-alkylamino-1, 3-dimethyluracils (5), with sodium azide in DMF at ambient temperature allowed the direct formation of the 8-substituted 1,3-dimethylxanthines (7) proceeding via a transient formation of the corresponding 5-azido-1 ,3-dimethyluracils. The 5-bromo-1,3-dimethyluracils (6f, g) possessing an ct-branched alkylamino group at the 6-position similarly react with sodium azide to afford 8,8-disubstituted 1,3-dimethyl-8H-xanthines (8,8-disubstituted 1,3-dimethyl-3,g-dihydropurine-2,6-diones)(8).