9-ethyl-6-(octylthio)-9H-purine | 15923-47-4

• 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: 9-ethyl-6-(octylthio)-9H-purine
• 英文别名: 9-Ethyl-6-(octylsulfanyl)-9h-purine；9-ethyl-6-octylsulfanylpurine
• CAS: 15923-47-4
• 化学式: C₁₅H₂₄N₄S
• 分子量: 292.448
• InChiKey: PAGXFUINSUTOJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-辛硫醇 、 6-methylthio-9-ethylpurine 在 1,10-菲罗啉 、 sodium carbonate 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以96%的产率得到9-ethyl-6-(octylthio)-9H-purine
  参考文献：
  名称：

  Direct Sulfenylation of the Purine C₈–H Bond with Thiophenols

  摘要：

  The one-step copper-mediated regioselective formation of the C-8-S bond for purine derivatives with arylthiols was achieved using air as the green oxidant in the presence of 1.0 equiv of Na2CO3 and stoichiometric CuCl and 1,10-phenanthroline monohydrate. This method provides an economical, easy-to-handle, and effective method for the synthesis of 8-sulfenylpurine derivatives in moderate to excellent yields. The reaction is selective for C8 over C2 and C6. It also tolerates a free amine on the purine, and it has a wide substrate scope.

  DOI：

  10.1021/acs.joc.9b03115

文献信息

• Direct Sulfenylation of the Purine C₈–H Bond with Thiophenols
  作者：Wei Jiang、Juanping Zhuge、Jianxiao Li、Gary Histand、Dongen Lin

  DOI：10.1021/acs.joc.9b03115

  日期：2020.2.21

  The one-step copper-mediated regioselective formation of the C-8-S bond for purine derivatives with arylthiols was achieved using air as the green oxidant in the presence of 1.0 equiv of Na2CO3 and stoichiometric CuCl and 1,10-phenanthroline monohydrate. This method provides an economical, easy-to-handle, and effective method for the synthesis of 8-sulfenylpurine derivatives in moderate to excellent yields. The reaction is selective for C8 over C2 and C6. It also tolerates a free amine on the purine, and it has a wide substrate scope.