(E)-1-<2,2-bis(hydroxymethyl)cyclopropyl>-5-(2-carboxyvinyl)uracil | 145215-19-6

• 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: (E)-1-<2,2-bis(hydroxymethyl)cyclopropyl>-5-(2-carboxyvinyl)uracil
• 英文别名: (E)-3-[1-[2,2-bis(hydroxymethyl)cyclopropyl]-2,4-dioxopyrimidin-5-yl]prop-2-enoic acid
• CAS: 145215-19-6
• 化学式: C₁₂H₁₄N₂O₆
• 分子量: 282.253
• InChiKey: RGNMCQKAYYVTKE-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1-<2,2-bis(hydroxymethyl)cyclopropyl>-5-(2-carboxyvinyl)uracil 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以44.6%的产率得到(E)-1-<2,2-bis(hydroxymethyl)cyclopropyl>-5-(2-bromovinyl)uracil
  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
• 作为产物：
  描述：

  N-<2,2-bis(benzyloxymethyl)cyclopropyl>urea 在 palladium diacetate 、 钯 吡啶 、 ammonium hydroxide 、 sodium hydroxide 、 甲酸 、 ammonium cerium(IV) nitrate 、 sodium methylate 、 三乙胺 、 三苯基膦 、 lithium iodide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 25.0~85.0 ℃ 、101.33 kPa 条件下， 反应 32.0h， 生成 (E)-1-<2,2-bis(hydroxymethyl)cyclopropyl>-5-(2-carboxyvinyl)uracil
  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.