(+/-)-9-[4,4-bis(hydroxymethyl)-5-methylenecyclopent-2-enyl]adenine | 1160714-25-9

• 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-[4,4-bis(hydroxymethyl)-5-methylenecyclopent-2-enyl]adenine
• 英文别名: [4-(6-Aminopurin-9-yl)-1-(hydroxymethyl)-5-methylene-cyclopent-2-en-1-yl]methanol；[4-(6-aminopurin-9-yl)-1-(hydroxymethyl)-5-methylidenecyclopent-2-en-1-yl]methanol
• CAS: 1160714-25-9
• 化学式: C₁₃H₁₅N₅O₂
• 分子量: 273.294
• InChiKey: ADCAJQAPLGIFEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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-[4,4-bis(hydroxymethyl)-5-methylenecyclopent-2-enyl]-6-chloropurine 在 氨 作用下， 以 甲醇 为溶剂， 以70%的产率得到(+/-)-9-[4,4-bis(hydroxymethyl)-5-methylenecyclopent-2-enyl]adenine
  参考文献：
  名称：

  Novel Synthesis and Anti-HIV Activity of 4′-Branched Exomethylene Carbocyclic Nucleosides Using a Ring-Closing Metathesis of Triene

  摘要：

  The exomethylene of 6 was successfully constructed from the aldehyde 5 using Eschenmoser's reagents. A triene compound 7 was cyclized successfully using Grubbs' II catalyst to give an exomethylene carbocycle nucleus for the target compound. A Mitsunobu reaction was successfully used to condense the natural bases (adenine, thymine, uracil, and cytosine). The synthesized cytosine analogue 20 showed moderate anti-HIV activity (EC50 = 10.67 M).

  DOI：

  10.1080/15257770802458246