9-benzyl-2-ethenyl-9H-purine | 226247-84-3

• 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-2-ethenyl-9H-purine
• 英文别名: 9-Benzyl-2-vinyl-purine；9-benzyl-2-ethenylpurine
• CAS: 226247-84-3
• 化学式: C₁₄H₁₂N₄
• 分子量: 236.276
• InChiKey: UOYKERPOCOYHKE-UHFFFAOYSA-N

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：

  丙二酸二乙酯 、 9-benzyl-2-ethenyl-9H-purine 在 sodium hydride 作用下， 生成 9-benzyl-2-<3,3-bis(ethoxycarbonyl)propyl>-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-苄基-6-氯嘌呤-2-胺 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 、 二碘甲烷 、 氢气 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 25.0~60.0 ℃ 、344.74 kPa 条件下， 反应 31.0h， 生成 9-benzyl-2-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.