6-o-tolylsulfanyl-7(9)H-purine | 5461-10-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-o-tolylsulfanyl-7(9)H-purine
• 英文别名: 6-o-tolylmercapto-7(9)H-purine；6-o-Tolylmercapto-7(9)H-purin；6-(2-methylphenyl)sulfanyl-7H-purine
• CAS: 5461-10-9
• 化学式: C₁₂H₁₀N₄S
• 分子量: 242.304
• InChiKey: POKUSGFCHPTISZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-巯基甲苯 、 6-氯嘌呤 在 水 作用下， 反应 4.0h， 以92%的产率得到6-o-tolylsulfanyl-7(9)H-purine
  参考文献：
  名称：

  Catalyst-Free and Base-Free Water-Promoted SNAr Reaction of Heteroaryl Halides with Thiols

  摘要：

  在水相中，已开发出一种简单高效的合成联芳基硫醚的路线，无需碱和催化剂。各种杂芳基卤化物和硫醇通过SNAr反应，以良好至优异的产率提供了二芳基硫醚。该反应的显著关键特征包括使用水作为廉价且环境友好的反应介质，无需任何额外试剂或催化剂，以及产品易于分离。

  DOI：

  10.1055/s-0029-1216644

文献信息

• Antimycobacterial Agents. 1. Thio Analogues of Purine
  作者：Ashish K. Pathak、Vibha Pathak、Lainne E. Seitz、William J. Suling、Robert C. Reynolds

  DOI：10.1021/jm030389b

  日期：2004.1.1

  Thio analogues of purine, pyridine, and pyrimidine were prepared based on the initial activity screening of several analogues of these heterocycles against Mycobacterium tuberculosis (Mtb). Certain 6-thio-substituted purine analogues described herein showed moderate to good inhibitory activity. In particular, two purine analogues 9-(ethylcarboxymethyl)-6-(decylthio)9H-purine (20) and 9-(ethylcarboxymethyl)-6-(dodecylthio)-9H-purine (21) exhibited MIC values of 1.56 and 0.78 mug/mL respectively against the Mtb H(37)Rv strain. N-9-Substitution apparently enhances the antimycobacterial activity in the purine series described herein.
• Copper Catalyzed Three-Component Ullmann C–S Coupling in PEG for the Synthesis of 6-Aryl/alkylthio-purines
  作者：Panpan Zhang、Yunfang Liu、Xulian Li、Geling Siri、Jieyuan Wang、Zhen Li、Yajun Jian、Ziwei Gao

  DOI：10.1021/acs.joc.3c02116

  日期：2024.2.16
• Catalyst-Free and Base-Free Water-Promoted SNAr Reaction of Heteroaryl Halides with Thiols
  作者：B. Sreedhar、P. Reddy、M. Reddy

  DOI：10.1055/s-0029-1216644

  日期：2009.5

  A simple and efficient route for the synthesis of biaryl sulfides have been developed in aqueous medium under base- and catalyst-free conditions. A wide variety of heteroaryl halides and thiols underwent SNAr reaction to provide diaryl sulfides in good to excellent yields. The remarkable key features of the reaction include the use of water as an inexpensive and environmentally benign reaction medium, absence of any additional reagent or catalyst, and easy isolation of the products.

  在水相中，已开发出一种简单高效的合成联芳基硫醚的路线，无需碱和催化剂。各种杂芳基卤化物和硫醇通过SNAr反应，以良好至优异的产率提供了二芳基硫醚。该反应的显著关键特征包括使用水作为廉价且环境友好的反应介质，无需任何额外试剂或催化剂，以及产品易于分离。