9-(2-nitro-phenyl)-9H-purin-6-ylamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 9-(2-nitro-phenyl)-9H-purin-6-ylamine
• 英文别名: 9-(2-Nitro-phenyl)-9h-purin-6-ylamine；9-(2-nitrophenyl)purin-6-amine
• 化学式: C₁₁H₈N₆O₂
• 分子量: 256.224
• InChiKey: CGMGGNGGPCTAKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-(2-nitro-phenyl)-9H-purin-6-ylamine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以89%的产率得到9-(2-aminophenyl)adenine
  参考文献：
  名称：

  Direct Arylation of Adenine by Fluoro- and Chloronitrobenzenes: Effect of Microwaves

  摘要：

  Direct arylation of adenine with fluoro- and chloronitrobenzenes leads to mixtures of N9 and N7 substituted adenines. After separation by column chromatography, the individual isomers can be efficiently hydrogenated on Pd to give the corresponding aminophenyladenines. A significant enhancement of the reaction rate by microwave irradiation was observed. This two-step procedure was found to be a feasible route to otherwise hardly available 7-aminophenyladenines. Correlation between calculated shielding constants and experimental values of chemical shifts in C-13 and N-15 NMR was used for assignment of the site of substitution. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.831902
• 作为产物：
  描述：

  硝基氯苯 、 腺嘌呤 在 silica gel 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.04h， 以65%的产率得到9-(2-nitro-phenyl)-9H-purin-6-ylamine
  参考文献：
  名称：

  Microwave-assisted N-nitroarylation of some pyrimidine and purine nucleobases

  摘要：

  介绍了一种在二氧化硅和Cs2CO3存在下，以二甲基亚砜（DMSO）为均质溶剂，通过微波辅助核碱基的N-硝基芳基化，合成一些核碱基的N-硝基芳基衍生物的有效方法。关键词：微波；N-硝基芳基化；嘧啶；嘌呤；SNAr。

  DOI：

  10.1139/v06-119

文献信息

• Regioselective N‐Arylation of Some Pyrimidine and Purine Nucleobases
  作者：Ali Khalafi‐Nezhad、Abdolkarim Zare、Abolfath Parhami、Mohammad Navid Soltani Rad、Gholam Reza Nejabat

  DOI：10.1080/00397910600943535

  日期：2006.11.1

  Abstract N‐Arylation of some pyrimidine and purine nucleobases in the presence of SiO2 and Cs2CO3 under solvent‐free as well as in solution conditions is described. In these conditions, N1‐aryl pyrimidines and N9‐aryl purines have been obtained regioselectively in moderate to high yields with relatively short reaction times.

  摘要 描述了在无溶剂和溶液条件下，在 SiO2 和 Cs2CO3 存在下一些嘧啶和嘌呤核碱基的 N-芳基化。在这些条件下，N1-芳基嘧啶和N9-芳基嘌呤可以区域选择性地以中等至高产率和相对较短的反应时间获得。
• A highly efficient protocol for the synthesis of N-aryl nucleobases using zinc oxide in ionic liquids
  作者：A. Zare、A. Hasaninejad、A. Khalafi-Nezhad、A. R. Moosavi-Zare、M. H. Beyzavi、F. Khedri、F. Asadi、N. Hayati、A. Asifi

  DOI：10.1007/bf03246033

  日期：2010.6

  A highly efficient and simple method for the synthesis of N-aryl derivatives of pyrimidine and purine nucleobases via N-arylation of nucleobases using zinc oxide in 1-butyl-3-methylimidazolium bromide ([bmim]Br) under microwave as well as thermal conditions is described. In both conditions, the title compounds were produced in high to excellent yields and in short reaction times.
• Microwave-assisted N-nitroarylation of some pyrimidine and purine nucleobases
  作者：Ali Khalafi-Nezhad、Abdolkarim Zare、Abolfath Parhami、Mohammad Navid Soltani Rad、Gholam Reza Nejabat

  DOI：10.1139/v06-119

  日期：2006.7.1

  An efficient procedure for the synthesis of some N-nitroaryl derivatives of nucleobases via microwave-assisted N-nitroarylation of nucleobases in the presence of SiO₂ and Cs₂CO₃ in DMSO, as the homogenizing solvent, is described. In this method, some pyrimidine and purine nucleobases are nitroarylated regioselectively in moderate to high yields and short reaction times.Key words: microwave, N-nitroarylation, pyrimidine, purine, SN_Ar.

  介绍了一种在二氧化硅和Cs2CO3存在下，以二甲基亚砜（DMSO）为均质溶剂，通过微波辅助核碱基的N-硝基芳基化，合成一些核碱基的N-硝基芳基衍生物的有效方法。关键词：微波；N-硝基芳基化；嘧啶；嘌呤；SNAr。
• Direct Arylation of Adenine by Fluoro- and Chloronitrobenzenes: Effect of Microwaves
  作者：Lubomír Váňa、Lukáš Vrzal、Hana Dvořáková、Michal Himl、Igor Linhart

  DOI：10.1080/00397911.2013.831902

  日期：2014.3.19

  Direct arylation of adenine with fluoro- and chloronitrobenzenes leads to mixtures of N9 and N7 substituted adenines. After separation by column chromatography, the individual isomers can be efficiently hydrogenated on Pd to give the corresponding aminophenyladenines. A significant enhancement of the reaction rate by microwave irradiation was observed. This two-step procedure was found to be a feasible route to otherwise hardly available 7-aminophenyladenines. Correlation between calculated shielding constants and experimental values of chemical shifts in C-13 and N-15 NMR was used for assignment of the site of substitution. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]