6-Amino-3,7-dimethyl-3,7-dihydro-purin-8-one | 198758-31-5

• 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: 6-Amino-3,7-dimethyl-3,7-dihydro-purin-8-one
• 英文别名: 6-amino-3,7-dimethylpurin-8-one
• CAS: 198758-31-5
• 化学式: C₇H₉N₅O
• 分子量: 179.181
• InChiKey: KKDWEGNZDXDFGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  78.73
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-Amino-3,7-dimethyl-3,7-dihydro-purin-8-one 、 碘甲烷 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 生成 6-Imino-3,7,9-trimethyl-3,6,7,9-tetrahydro-purin-8-one; hydriodide
  参考文献：
  名称：

  Purines. LXXVI. Alkylation of 8-Oxoadenine Derivatives: Syntheses of 3,7-Dialkyl-, 3,9-Dialkyl-, and 3,7,9-Trialkyl-8-oxoadenines.

  摘要：

  d, h·HCl·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H

  DOI：

  10.1248/cpb.45.1582
• 作为产物：
  描述：

  8-Methoxy-3,7-dimethyl-3,7-dihydro-purin-6-ylideneamine; hydriodide 在 盐酸 作用下， 反应 2.0h， 以10.1 mg的产率得到6-Amino-3,7-dimethyl-3,7-dihydro-purin-8-one
  参考文献：
  名称：

  Purines. LXXVI. Alkylation of 8-Oxoadenine Derivatives: Syntheses of 3,7-Dialkyl-, 3,9-Dialkyl-, and 3,7,9-Trialkyl-8-oxoadenines.

  摘要：

  d, h·HCl·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H

  DOI：

  10.1248/cpb.45.1582

文献信息

• Purines. LXXVI. Alkylation of 8-Oxoadenine Derivatives: Syntheses of 3,7-Dialkyl-, 3,9-Dialkyl-, and 3,7,9-Trialkyl-8-oxoadenines.
  作者：Taisuke ITAYA、Yasutaka TAKADA、Tae KANAI、Miki KANEKO、Tozo FUJII

  DOI：10.1248/cpb.45.1582

  日期：——

  3-Alkyl-8-hydroxyadenines (5) have been shown to undergo regioselective methylation at the 7- or 9-position depending on the reaction conditions. Thus, treatment of 5a, c with dimetyl sulfate in aqueous NaOH provided 3-alkyl-7-methyl-8-oxoadenines (6b, h) in 48-60% yields, together with 3-alkyl-8-methoxyadenines 4d, h), whereas treatment of 5a-c with MeI in AcNMe2 at 40°C for 48h and subsequent anion exchange afforded 3-alkyl-9-methyl-8-oxoadenine hydrochlorides (7d, g, h·HCl) in 50-59% yieds. However, the reactions of 5a, c with EtI or PhCH2Br took place slowly, giving complex mixtures of products.Compounds 6d, h were alternatively prepared in 51% and 31% yields, respectively, together with 3-alkyl-7, 9-dimethyl-8-oxoadenine hydrochlorides (11d, h·HCl), by treatment of 3-alkyl-8-methoxyadenines (4d, h) with MeI in AcNMe2 at room temperature for 6 h, followed by hydrolysis with boiling aqueous HCl. This method was applicable to ethylation with EtI, and 7-ethyl-3-methyl-8-oxoadenine (6e) was obtained in 70% yield from 8-ethoxy-3-methyladenine (4e). Compound 11h was shown to be obtainable through futher methylation of 6h. Thus, 11d, h were prepared in good yields by treatment of 6d, h with MeI in AcNMe2.Compounds 7, to which zwitterionic structures were assigned, were stable in 0.1 N aqueous NaOH at room temperature, whereas 11d, h were no longer stable under such conditions.

  d, h·HCl·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H2O·H