6-(p-toluenesulfonyl)-9-phenyl-9H-purine | 62141-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(p-toluenesulfonyl)-9-phenyl-9H-purine
• 英文别名: 6-tosyl-9-phenyl-9H-purine；9-phenyl-6-(toluene-4-sulfonyl)-9H-purine；9-Phenyl-6-(p-toluolsulfonyl)-9H-purin；6-(4-Methylbenzene-1-sulfonyl)-9-phenyl-9H-purine；6-(4-methylphenyl)sulfonyl-9-phenylpurine
• CAS: 62141-41-7
• 化学式: C₁₈H₁₄N₄O₂S
• 分子量: 350.401
• InChiKey: GMRJRPUYXAZWAY-UHFFFAOYSA-N

物化性质

• 熔点：
  230-231 °C
• 沸点：
  601.1±65.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(p-toluenesulfonyl)-9-phenyl-9H-purine 、 氰化钾 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以88%的产率得到3-phenyl-9H-purine-6-carbonitrile
  参考文献：
  名称：

  Preparation of Heteroarenecarbonitriles by Reaction of Haloheteroarenes with Potassium Cyanide Catalyzed by Sodium p-Toluenesulfinate

  摘要：

  Several heteroarenecarbonitriles were prepared by reaction of haloheteroarenes with potassium cyanide catalyzed by sodium p-toluenesulfinate (1) or sodium methanesulfinate (2). In the reaction pathway, the cyanation proceeds through the formation of the sulfonylheteroarenes.

  DOI：

  10.3987/com-94-s(b)38
• 作为产物：
  描述：

  1,9-dihydro-9-phenyl-6H-purine-6-thione 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 6-(p-toluenesulfonyl)-9-phenyl-9H-purine
  参考文献：
  名称：

  Electrophilic Cyanations. I. Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p-Toluenesulfonyl Cyanide

  摘要：

  Mercaptoheteroarenes (1) underwent electrophilic cyanation with p-toluenesulfonyl cyanide (TsCN) in THF in the presence of NaH to give the corresponding thiocyanatoheteroarenes (2) in moderate to good yields. In DMF, tosylheteroarenes (4) were formed by substitution with p-toluenesulfinate ion through thiocyanatoheteroarenes (2).

  DOI：

  10.3987/com-97-7740

文献信息

• Electrophilic Cyanations. I. Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p-Toluenesulfonyl Cyanide
  作者：Akira Miyashita、Izuru Nagasaki、Akiko Kawano、Yumiko Suzuki、Ken-ichi Iwamoto、Takeo Higashino

  DOI：10.3987/com-97-7740

  日期：——

  Mercaptoheteroarenes (1) underwent electrophilic cyanation with p-toluenesulfonyl cyanide (TsCN) in THF in the presence of NaH to give the corresponding thiocyanatoheteroarenes (2) in moderate to good yields. In DMF, tosylheteroarenes (4) were formed by substitution with p-toluenesulfinate ion through thiocyanatoheteroarenes (2).
• Preparation of Heteroarenecarbonitriles by Reaction of Haloheteroarenes with Potassium Cyanide Catalyzed by Sodium p-Toluenesulfinate
  作者：Akira Miyashita、Yumiko Suzuki、Kiyono Ohta、Takeo Higashino

  DOI：10.3987/com-94-s(b)38

  日期：——

  Several heteroarenecarbonitriles were prepared by reaction of haloheteroarenes with potassium cyanide catalyzed by sodium p-toluenesulfinate (1) or sodium methanesulfinate (2). In the reaction pathway, the cyanation proceeds through the formation of the sulfonylheteroarenes.