4-amino-1-<2,2-bis(hydroxymethyl)cyclopropyl>pyrimidin-2(1H)-one | 145215-22-1

• 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: 4-amino-1-<2,2-bis(hydroxymethyl)cyclopropyl>pyrimidin-2(1H)-one
• 英文别名: 4-Amino-1-[2,2-bis(hydroxymethyl)cyclopropyl]pyrimidin-2-one
• CAS: 145215-22-1
• 化学式: C₉H₁₃N₃O₃
• 分子量: 211.221
• InChiKey: VOTLJNKOUOLATK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-<2,2-bis(benzyloxymethyl)cyclopropyl>urea 在 钯 吡啶 、 ammonium hydroxide 、 甲酸 、 2-氯苯基二氯膦 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 25.0~85.0 ℃ 、101.33 kPa 条件下， 反应 121.5h， 生成 4-amino-1-<2,2-bis(hydroxymethyl)cyclopropyl>pyrimidin-2(1H)-one
  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

• Synthesis of carbocyclic nucleosides: synthesis of (±)-2,2-bis(hydroxymethyl)cyclopropyl nucleosides
  作者：Takao Izawa、Shigeru Nishiyama、Shosuke Yamamura、Kuniki Kato、Tomohisa Takita

  DOI：10.1039/p19920002519

  日期：——

  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.