2-(9-benzyl-9H-purin-6-yl)-5-methyl-1,3-phenylene diacetate | 1447307-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(9-benzyl-9H-purin-6-yl)-5-methyl-1,3-phenylene diacetate
• 英文别名: [3-Acetyloxy-2-(9-benzylpurin-6-yl)-5-methylphenyl] acetate
• CAS: 1447307-96-1
• 化学式: C₂₃H₂₀N₄O₄
• 分子量: 416.436
• InChiKey: JWUQYMUGSKQOKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  96.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  9-benzyl-6-(p-tolyl)-9H-purine 、 碘苯二乙酸 在 palladium diacetate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以68%的产率得到2-(9-benzyl-9H-purin-6-yl)-5-methyl-1,3-phenylene diacetate
  参考文献：
  名称：

  Purinyl N1-Directed Aromatic C–H Oxidation in 6-Arylpurines and 6-Arylpurine Nucleosides

  摘要：

  Palladium-catalyzed C-H bond activation and oxidation of C6 arylpurines as well as C6 arylpurine nucleosides can be accomplished using Pd(OAc)(2)/PhI(OAc)(2) in CH3CN. Despite the presence of four nitrogen atoms in the purine moiety as well as the polyoxygenated saccharide and a labile glycosidic bond in the nucleosides, these reactions can be effectively conducted. Notably, the generally more labile 2'-deoxyribonucleosides also undergo reaction. The reaction conditions can be tuned to yield either monoacetoxylated or diacetoxylated products predominantly. In the course of these investigations, a dimeric Pe(II)-containing cyclopalladated C6 naphthylpurine derivative has been obtained and crystallographically characterized. This compound is competent in catalyzing the oxidization with PhI(OAc)(2), indicating its plausible intermediacy in the chemistry. The X-ray structure of a monoacetoxylated product from this reaction has also been obtained.

  DOI：

  10.1021/jo4008282