9-<2,2-bis(hydroxymethyl)cyclopropyl>adenine | 135345-82-3

• 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: 9-<2,2-bis(hydroxymethyl)cyclopropyl>adenine
• 英文别名: [2-(6-Aminopurin-9-yl)-1-(hydroxymethyl)cyclopropyl]methanol
• CAS: 135345-82-3
• 化学式: C₁₀H₁₃N₅O₂
• 分子量: 235.246
• InChiKey: CGWDPLAYJXVVEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  9-<2,2-bis(benzyloxymethyl)cyclopropyl>-6-chloropurine 在 钯 甲酸 、 氨 作用下， 以 甲醇 为溶剂， 25.0~100.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 9-<2,2-bis(hydroxymethyl)cyclopropyl>adenine
  参考文献：
  名称：

  Synthesis of carbocyclic nucleosides: synthesis of (±)-2,2-bis(hydroxymethyl)cyclopropyl nucleosides

  摘要：

  Treatment of 2,2-bis(benzyloxymethyl)cyclopropanecarboxylic acid 8 with ethyl chloroformate and sodium azide followed by thermolysis of the resulting keto azide 9 at 80-degrees-C provided the corresponding isocyanate 10, which was then converted into 2,2-bis(benzyloxymethyl)cyclopropylurea 11 and 2, 2-bis(benzyloxymethyl)cyclopropylamine 13. The racemic 2,2-bis(hydroxymethyl)cyclopropylpyrimidine nucleosides 16, 21, 22, 23, 26, 29, and 31 and the purine nucleosides 39 and 41 were prepared from compounds 11 and 13, respectively; they showed no antiviral activity against HSV-1, HSV-2, HCMV, and HIV-1 in cell culture.

  DOI：

  10.1039/p19920002519

文献信息

• Syntheses of 2,2-bishydroxymethylcyclopropyl adenine and uracil, novel carbocyclic nucleosides
  作者：Shigeru Nishiyama、Shinya Ueki、Tatsuya Watanabe、Shosuke Yamamura、Kuniki Kato、Tomohisa Takita

  DOI：10.1016/s0040-4039(00)71258-5

  日期：1991.5

  Novel carbocyclic nucleoside, 2,2-bishydroxymethylcyclopropyl adenine and uracil were successfully synthesized.