1',3'-dimethyl-3'H-spiro[cyclohexane-1,8'-purine]-2',6'-dione | 727-11-7

• 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'-dimethyl-3'H-spiro[cyclohexane-1,8'-purine]-2',6'-dione
• 英文别名: 1',3'-dimethylspiro[cyclohexane-1,8'-purine]-2',6'(1'H,3'H)-dione；1',3'-dimethylspiro[cyclohexane-1,8'-purine]-2',6'-dione
• CAS: 727-11-7
• 化学式: C₁₂H₁₆N₄O₂
• 分子量: 248.285
• InChiKey: TWIOWKHTTGCXPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  5-bromo-6-cyclohexylamino-1,3-dimethyluracil 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到1',3'-dimethyl-3'H-spiro[cyclohexane-1,8'-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).