acetic acid 2-(9-benzyl-9H-purin-6-yl)-5-methyl-phenyl ester | 1310063-78-5

• 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: acetic acid 2-(9-benzyl-9H-purin-6-yl)-5-methyl-phenyl ester
• CAS: 1310063-78-5
• 化学式: C₂₁H₁₈N₄O₂
• 分子量: 358.4
• InChiKey: AUZDUWYGLSAFOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  69.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  acetic acid 2-(9-benzyl-9H-purin-6-yl)-5-methyl-phenyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以22.4 mg的产率得到2-(9-benzyl-9H-purin-6-yl)-5-methylphenol
  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
• 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， 生成 acetic acid 2-(9-benzyl-9H-purin-6-yl)-5-methyl-phenyl ester
  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

文献信息

• Palladium-catalyzed C–H bond functionalization of C6-arylpurines
  作者：Hai-Ming Guo、Wei-Hao Rao、Hong-Ying Niu、Li-Li Jiang、Ge Meng、Jia-Jia Jin、Xi-Ning Yang、Gui-Rong Qu

  DOI：10.1039/c1cc11135c

  日期：——

  A highly regioselective Pd-catalyzed C_Ar–H bond activation method was developed for the modification of purines (nucleosides) with different functional groups by using purine as a directing group. This approach provides a new access to a variety of functionalized purines (nucleosides).

  开发了一种高度区域选择性的Pd催化的C_Ar–H键活化方法，用于利用嘌呤作为定向基团对带有不同功能基团的嘌呤（核苷）进行改性。这种方法为多种官能化的嘌呤（核苷）提供了新的途径。