(E)-9-[2-bromo-4-(tert-butyldimethylsilanyloxy)-3-phenyl-but-2-enyl]-adenine | 940293-05-0

• 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: (E)-9-[2-bromo-4-(tert-butyldimethylsilanyloxy)-3-phenyl-but-2-enyl]-adenine
• CAS: 940293-05-0
• 化学式: C₂₁H₂₈BrN₅OSi
• 分子量: 474.476
• InChiKey: RLWXJHDCMSWPPH-MSUUIHNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.85
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-9-[2-bromo-4-(tert-butyldimethylsilanyloxy)-3-phenyl-but-2-enyl]-adenine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以68%的产率得到(E)-1-(2-bromo-4-hydroxy-3-phenyl-but-2-enyl)adenine
  参考文献：
  名称：

  Simple Synthesis of Novel Acyclic (E)-Bromovinyl Nucleosides as Potential Antiviral Agents

  摘要：

  In these study, novel acyclic ( E )-bromovinyl nucleosides were synthesized as potential antiviral agents. The coupling of the allylic bromide 9 with bases (thymine, uracil, 5-fluorouracul, 5-iodouracil, cytosine, adenine) afforded a series of novel acyclic nucleosides. The synthesized compounds were evaluated for their antiviral activity against various viruses such as HIV-1, HSV-1, HSV-2, and HCMV. 5-Iodouracil analogue 19 showed weak anti-HIV-1 activity.

  DOI：

  10.1080/15257770600793877
• 作为产物：
  描述：

  (Z)-4-(t-butyldimethylsilyloxy)-3-phenyl-but-2-enoic acid ethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 溴 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氯化碳 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 (E)-9-[2-bromo-4-(tert-butyldimethylsilanyloxy)-3-phenyl-but-2-enyl]-adenine
  参考文献：
  名称：

  Simple Synthesis of Novel Acyclic (E)-Bromovinyl Nucleosides as Potential Antiviral Agents

  摘要：

  In these study, novel acyclic ( E )-bromovinyl nucleosides were synthesized as potential antiviral agents. The coupling of the allylic bromide 9 with bases (thymine, uracil, 5-fluorouracul, 5-iodouracil, cytosine, adenine) afforded a series of novel acyclic nucleosides. The synthesized compounds were evaluated for their antiviral activity against various viruses such as HIV-1, HSV-1, HSV-2, and HCMV. 5-Iodouracil analogue 19 showed weak anti-HIV-1 activity.

  DOI：

  10.1080/15257770600793877