9-benzyl-8-iodo-9H-purine | 226247-61-6

• 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-iodo-9H-purine
• 英文别名: 9-benzyl-8-iodopurine
• CAS: 226247-61-6
• 化学式: C₁₂H₉IN₄
• 分子量: 336.135
• InChiKey: BPAHWHJCLRUJOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  9-benzyl-8-iodo-9H-purine 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 zinc(II) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 139.0h， 生成 exo-9-benzyl-8-(bicyclo<2.2.1>hept-5-en-2-yl)-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 C₉H₁₉ClMgN*LiCl 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 以84%的产率得到9-benzyl-8-iodo-9H-purine
  参考文献：
  名称：

  Regioselective Functionalization of Purine Derivatives at Positions 8 and 6 Using Hindered TMP-Amide Bases of Zn and Mg

  摘要：

  A broad range of purine derivatives were efficiently metalated at positions 8 and 6 using TMP-amide bases. This provided polysubstituted purines in good to very good yields after subsequent trapping of the zinc or magnesium intermediates with various electrophiles.

  DOI：

  10.1055/s-0033-1338524