2-amino-6-dimethylamino-9-benzyl purine | 917240-77-8

• 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: 2-amino-6-dimethylamino-9-benzyl purine
• 英文别名: 9-benzyl-6-N,6-N-dimethylpurine-2,6-diamine
• CAS: 917240-77-8
• 化学式: C₁₄H₁₆N₆
• 分子量: 268.321
• InChiKey: UWZFWMFLAMSUFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-6-dimethylamino-9-benzyl purine 在 溴 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到2-amino-6-dimethylamino-8-bromo-9-benzylpurine
  参考文献：
  名称：

  Highly fluorescent donor–acceptor purines

  摘要：

  制备出的受体嘌呤在有机溶液中显示出近乎统一的荧光量子产率，这是将简单的生物相关杂环用于光电和光子应用的一个步骤。

  DOI：

  10.1039/b618171f
• 作为产物：
  描述：

  溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 70.0h， 生成 2-amino-6-dimethylamino-9-benzyl purine
  参考文献：
  名称：

  8-Bromination of 2,6,9-trisubstituted purines with pyridinium tribromide

  摘要：

  2,6,9-Trisubstituted purines are brominated in high yields using pyridinium tribromide as the brominating reagent. This procedure works excellently for electron-rich purines having electron-donating substituents at the 2- and 6-positions. The use of pyridinium tribromide, a crystalline alternative to elemental bromine, improves the bromination procedure for this type of substrate as the reagent is easy to handle and the work-up and purification procedures are simplified. (C) 2014 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2014.03.084

文献信息

• Self-complementary purines by quadruple hydrogen bonding
  作者：Alisha M. Martin、Roslyn S. Butler、Ion Ghiviriga、Rachel E. Giessert、Khalil A. Abboud、Ronald K. Castellano

  DOI：10.1039/b610239e

  日期：——

  The first discrete, self-complementary, quadruply hydrogen-bonded complexes based on the 2,6-diaminopurine (DAP) scaffold have been prepared; regioselective urea formation at the C(2) amino group of the heterocycle allows intermolecular dimerization (Kdim ∼ 1–1.6 × 103 M−1 in CDCl3) through a DADA hydrogen bonding motif.

  第一个基于 2,6-二氨基嘌呤 (DAP) 支架的离散、自互补、四重氢键复合物已制备完成；杂环的 C(2) 氨基上的区域选择性脲形成允许分子间二聚化 (Kdim ∼ 1–1.6 × 103 M−1 (CDCl3)) 通过 DADA 氢键结合基序。
• Highly fluorescent donor–acceptor purines
  作者：Roslyn S. Butler、Andrea K. Myers、Prabhu Bellarmine、Khalil A. Abboud、Ronald K. Castellano

  DOI：10.1039/b618171f

  日期：——

  Donor–acceptor purines have been prepared that show near unity fluorescence quantum yields in organic solution, a step toward using simple biorelevant heterocycles in optoelectronic and photonic applications.

  制备出的受体嘌呤在有机溶液中显示出近乎统一的荧光量子产率，这是将简单的生物相关杂环用于光电和光子应用的一个步骤。
• The optimized microwave-assisted decomposition of formamides and its synthetic utility in the amination reactions of purines
  作者：Lucie Čechová、Petr Jansa、Michal Šála、Martin Dračínský、Antonín Holý、Zlatko Janeba

  DOI：10.1016/j.tet.2010.12.040

  日期：2011.2

  The microwave-assisted decomposition of DMF was thoroughly studied and the reaction conditions (temperature, solvent effect, and effect of additives, such as acids, bases, and salts) were optimized for its use in amination reactions. The applicability of this expedient methodology in purine chemistry and with various formamides is demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.
• 8-Bromination of 2,6,9-trisubstituted purines with pyridinium tribromide
  作者：David Bliman、Mariell Pettersson、Mattias Bood、Morten Grøtli

  DOI：10.1016/j.tetlet.2014.03.084

  日期：2014.4

  2,6,9-Trisubstituted purines are brominated in high yields using pyridinium tribromide as the brominating reagent. This procedure works excellently for electron-rich purines having electron-donating substituents at the 2- and 6-positions. The use of pyridinium tribromide, a crystalline alternative to elemental bromine, improves the bromination procedure for this type of substrate as the reagent is easy to handle and the work-up and purification procedures are simplified. (C) 2014 The Authors. Published by Elsevier Ltd.