9-benzyl-2-iodo-9H-purine | 226247-82-1

• 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-iodo-9H-purine
• 英文别名: 9-Benzyl-2-iodo-purine；9-benzyl-2-iodopurine
• CAS: 226247-82-1
• 化学式: C₁₂H₉IN₄
• 分子量: 336.135
• InChiKey: NNFRBJUNMWKJLY-UHFFFAOYSA-N

物化性质

• 沸点：
  518.5±60.0 °C(Predicted)
• 密度：
  1.83±0.1 g/cm3(Predicted)

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-2-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 76.0h， 生成 endo-9-benzyl-2-(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-苄基-6-氯嘌呤-2-胺 在 palladium on activated charcoal 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 7.0h， 生成 9-benzyl-2-iodo-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

• 9-Benzylpurines with inhibitory activity against Mycobacterium tuberculosis
  作者：Anne Kristin Bakkestuen、Lise-Lotte Gundersen、Geir Langli、Fusheng Liu、Jens M.J Nolsøe

  DOI：10.1016/s0960-894x(00)00188-8

  日期：2000.6

  the 2-, 6- and/or 8-position have been prepared and screened for antimycobacterial effects. High inhibitory activity against Mycobacterium tuberculosis was found for 9-benzylpurines carrying a phenylethynyl-, trans-styryl or aryl substituents in the 6-position and generally chlorine in the 2-position tends to increase activity.

  已经制备了在2-，6-和/或8-位具有多种取代基的9-苄嘌呤，并对其抗分枝杆菌作用进行了筛选。发现对于在6-位带有苯基乙炔基，反式-苯乙烯基或芳基取代基的9-苄基嘌呤具有高的抗结核分枝杆菌活性，并且通常在2-位带有氯趋于增加活性。
• A New Sandmeyer Iodination of 2-Aminopurines in Non-aqueous Conditions: Combination of Alkali Metal Iodide and Iodine as Iodine Sources
  作者：Naoki Ozeki、Naoyuki Shimomura、andHitoshi Harada

  DOI：10.3987/com-00-9142

  日期：——

  An effective method for iodination using 2-aminopurines in non-aqueous conditions was found. The optimal conditions involved the combination of isopentyl nitrite, cuprous iodide, alkali metal iodide and iodine in ethylene glycol dimethyl ether at 60 degreesC.
• 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.