(+/-)-4,4-bis(tert-butyldimethylsilanyloxymethyl)-5-methylenecyclopent-2-enol | 1160714-21-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (+/-)-4,4-bis(tert-butyldimethylsilanyloxymethyl)-5-methylenecyclopent-2-enol
• CAS: 1160714-21-5
• 化学式: C₂₀H₄₀O₃Si₂
• 分子量: 384.707
• InChiKey: CMURFRUHTKOVBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+/-)-4,4-bis(tert-butyldimethylsilanyloxymethyl)-5-methylenecyclopent-2-enol 、 3-苯甲酰基尿嘧啶 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39%的产率得到(+/-)-1-[4,4-bis(tert-butyldimethylsilanyloxymethyl)-5-methylenecyclopent-2-enyl]-N(3)-benzoyluracil
  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：

  (+/-)-5,5-bis(tert-butyldimethylsilanyloxymethyl)-4-methylenehepta-1,6-dien-3-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到(+/-)-4,4-bis(tert-butyldimethylsilanyloxymethyl)-5-methylenecyclopent-2-enol
  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