9-benzyl-8-ethenyl-9H-purine | 226247-69-4

• 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-benzyl-8-ethenyl-9H-purine
• 英文别名: 9-Benzyl-8-vinyl-purine；9-benzyl-8-ethenylpurine
• CAS: 226247-69-4
• 化学式: C₁₄H₁₂N₄
• 分子量: 236.276
• InChiKey: PFDOYAAVYUTOLH-UHFFFAOYSA-N

物化性质

• 沸点：
  447.6±47.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯硫酚 、 9-benzyl-8-ethenyl-9H-purine 在 sodium hydride 作用下， 生成 9-benzyl-8-(2-phenylthioethyl)-9H-purine
  参考文献：
  名称：

  Addition and Cycloaddition to 2- and 8-Vinylpurines.

  摘要：

  The reactivity of purines carrying an alkenyl substituent in the 2- or 8-position in nucleophilic addition and cycloaddition reactions has been studied. A vinyl substituent situated at C-8 is highly electrophilic and readily participates as a Michael acceptor in nucleophilic additions and as a dienophile in Diels-Alder reactions. 2-Vinylpurines may also give addition and cycloaddition products. When benzenethiol was added to 9-benzyl-2-vinylpurine, both the simple adduct as well as 9-benzyl-2-(2-phenylthio-1-hydroxyethyl)-9H-purine were formed. The structure of the latter compound was determined by single-crystal X-ray methods.

  DOI：

  10.3891/acta.chem.scand.53-0269
• 作为产物：
  描述：

  9-benzyl-9H-purine 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 77.0h， 生成 9-benzyl-8-ethenyl-9H-purine
  参考文献：
  名称：

  Addition and Cycloaddition to 2- and 8-Vinylpurines.

  摘要：

  The reactivity of purines carrying an alkenyl substituent in the 2- or 8-position in nucleophilic addition and cycloaddition reactions has been studied. A vinyl substituent situated at C-8 is highly electrophilic and readily participates as a Michael acceptor in nucleophilic additions and as a dienophile in Diels-Alder reactions. 2-Vinylpurines may also give addition and cycloaddition products. When benzenethiol was added to 9-benzyl-2-vinylpurine, both the simple adduct as well as 9-benzyl-2-(2-phenylthio-1-hydroxyethyl)-9H-purine were formed. The structure of the latter compound was determined by single-crystal X-ray methods.

  DOI：

  10.3891/acta.chem.scand.53-0269

文献信息

• Addition and Cycloaddition to 2- and 8-Vinylpurines.
  作者：Fusheng Liu、Bjørn Dalhus、Lise-Lotte Gundersen、Frode Rise、Inger Søtofte、Jørgen Møller、Alexander Senning、Xin-Kan Yao、Hong-Gen Wang、J. -P. Tuchagues、Mattias Ögren

  DOI：10.3891/acta.chem.scand.53-0269

  日期：——

  The reactivity of purines carrying an alkenyl substituent in the 2- or 8-position in nucleophilic addition and cycloaddition reactions has been studied. A vinyl substituent situated at C-8 is highly electrophilic and readily participates as a Michael acceptor in nucleophilic additions and as a dienophile in Diels-Alder reactions. 2-Vinylpurines may also give addition and cycloaddition products. When benzenethiol was added to 9-benzyl-2-vinylpurine, both the simple adduct as well as 9-benzyl-2-(2-phenylthio-1-hydroxyethyl)-9H-purine were formed. The structure of the latter compound was determined by single-crystal X-ray methods.