9-(2,4-二硝基苯基)腺嘌呤 | 136112-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 9-(2,4-二硝基苯基)腺嘌呤
• 英文名称: 9-(2,4-dinitro-phenyl)-9H-purin-6-ylamine
• 英文别名: 9-(2,4-dinitrophenyl)-9H-purin-6-ylamine；9-(2,4-dinitrophenyl)-9H-purin-6-amine；9-(2,4-Dinitrophenyl)adenine；9-(2,4-dinitrophenyl)purin-6-amine
• CAS: 136112-73-7
• 化学式: C₁₁H₇N₇O₄
• 分子量: 301.221
• InChiKey: QPNNLHUBAVQESD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 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：
  161
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(2,4-二硝基苯基)腺嘌呤 、 巴比妥酸 、 对硝基苯甲醛 在 phosphotungstic acid 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以83%的产率得到9-[9-(2,4-dinitrophenyl)-9H-purin-6-yl]-10-(4-nitrophenyl)-9,10-dihydro-1H,8H-1,3,6,9-pentaazaantracene-2,4,5,7-tetraone
  参考文献：
  名称：

  Nucleosides as reagents in multicomponent reactions: one-pot synthesis of heterocyclic nucleoside analogues incorporating pyrimidine-fused rings

  摘要：

  In this study, a general and efficient protocol for the synthesis of new heterocyclic nucleoside analogues (HNAs), using a four-component coupling reaction of nucleosides, aldehydes, barbituric acid/2-thiobarbituric acid, or dimedone is described. The synthesized HNAs contain a pyrimidine-fused heterocycle coupled to the nucleoside via a C-N linkage. The nucleosides served as amine components and underwent the reaction in the presence of a catalytic amount of tungstophosphoric acid (H3PW12O40, TPA) in EtOH. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.003
• 作为产物：
  描述：

  腺嘌呤 、 1-氯-2,4-二硝基苯 在 四丁基溴化铵 、 silica gel 、 caesium carbonate 作用下， 反应 0.17h， 以87%的产率得到9-(2,4-二硝基苯基)腺嘌呤
  参考文献：
  名称：

  一些嘧啶和嘌呤核碱基的区域选择性 N-芳基化

  摘要：

  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。

  DOI：

  10.1080/00397910600943535

文献信息

• 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。
• 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.
• 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。
• Nucleosides as reagents in multicomponent reactions: one-pot synthesis of heterocyclic nucleoside analogues incorporating pyrimidine-fused rings
  作者：Ali Khalafi-Nezhad、Masoumeh Divar、Farhad Panahi

  DOI：10.1016/j.tetlet.2012.11.003

  日期：2013.1

  In this study, a general and efficient protocol for the synthesis of new heterocyclic nucleoside analogues (HNAs), using a four-component coupling reaction of nucleosides, aldehydes, barbituric acid/2-thiobarbituric acid, or dimedone is described. The synthesized HNAs contain a pyrimidine-fused heterocycle coupled to the nucleoside via a C-N linkage. The nucleosides served as amine components and underwent the reaction in the presence of a catalytic amount of tungstophosphoric acid (H3PW12O40, TPA) in EtOH. (c) 2012 Elsevier Ltd. All rights reserved.