9-benzyl-8-(o-tolyl)-9H-purin-6-amine | 1095585-34-4

• 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-benzyl-8-(o-tolyl)-9H-purin-6-amine
• CAS: 1095585-34-4
• 化学式: C₁₉H₁₇N₅
• 分子量: 315.377
• InChiKey: DVDKNYNJBCNDLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  69.62
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-碘代甲苯 、 9-苄基-9h-嘌呤-6-胺 在 copper(l) iodide 、 Pd(OH)2/C 、 caesium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 0.25h， 以42%的产率得到9-benzyl-8-(o-tolyl)-9H-purin-6-amine
  参考文献：
  名称：

  Microwave-assisted Pd(OH)2-catalyzed direct C−H arylation of free-(NH2) adenines with aryl halides

  摘要：

  A direct C-H arylation of free-(NH2) adenines using Pd(OH)(2)/C (Pearlman's catalyst) and stoichiometric amount of copper iodide under ligandless microwave activation is described. This new protocol proved to be highly effective to synthesize a variety of 8-aryladenine derivatives 3 without prior protection of the amino substituent. The arylation reaction takes place rapidly within few Minutes and allows the coupling to proceed regioselectively at the 8-position with a wide range of aryl halides including aryl iodides, bromides and the less reactive aryl chlorides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.021

文献信息

• A site selective C–H arylation of free-(NH2) adenines with aryl chlorides: Application to the synthesis of 6,8-disubstituted adenines
  作者：Sophian Sahnoun、Samir Messaoudi、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1039/b912033e

  日期：——

  An efficient site selective method for the direct arylation of free-(NH2) adenines 1 to provide a range of C-8 arylated adenines 3 in excellent yields is described. This process based on the use of Pd(OH)2/C as the catalyst and a stoichiometric amount of CuI under ligandless conditions is general. It allows the coupling to proceed with a variety of aryl halides, including for the first time cheaper

  描述了一种用于自由-（NH 2）腺嘌呤1的直接芳基化的有效位点选择方法，以优异的产率提供了一系列C-8芳基化的腺嘌呤3。通常基于在无配体条件下使用Pd（OH）2 / C作为催化剂和化学计量的CuI的方法。它可以使偶联反应与各种芳基卤化物进行，包括第一次更便宜，反应性更低的芳基氯化物。还报道了该方法的扩展用于顺序制备非对称的C8 / N 6-芳基腺嘌呤4。