(+/-)-1-[4,4-bis(tert-butyldimethylsilanyloxymethyl)-5-methylenecyclopent-2-enyl]-N(3)-benzoylthymine | 1160714-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: (+/-)-1-[4,4-bis(tert-butyldimethylsilanyloxymethyl)-5-methylenecyclopent-2-enyl]-N(3)-benzoylthymine
• CAS: 1160714-27-1
• 化学式: C₃₂H₄₈N₂O₅Si₂
• 分子量: 596.915
• InChiKey: WRVHAXUGYYIIOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  79.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (+/-)-1-[4,4-bis(tert-butyldimethylsilanyloxymethyl)-5-methylenecyclopent-2-enyl]-N(3)-benzoylthymine 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以73%的产率得到(+/-)-1-[4,4-bis(hydroxymethyl)-5-methylenecyclopent-2-enyl]-N(3)-benzoylthymine
  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
• 作为产物：
  描述：

  (+/-)-4,4-bis(tert-butyldimethylsilanyloxymethyl)-5-methylenecyclopent-2-enol 、 N-3-benzoylthymine 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 以43%的产率得到(+/-)-1-[4,4-bis(tert-butyldimethylsilanyloxymethyl)-5-methylenecyclopent-2-enyl]-N(3)-benzoylthymine
  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