2-[(4-methoxybenzyl)thio]pyrimidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[(4-methoxybenzyl)thio]pyrimidine
• 英文别名: 2-[(4-Methoxyphenyl)methylsulfanyl]pyrimidine
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: RPEGHOSCPFJLGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯硼酸 、 2-[(4-methoxybenzyl)thio]pyrimidine 在 四(三苯基膦)钯 、 噻吩-2-甲酸亚铜(I) 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以73%的产率得到2-(4-甲氧基苯基)嘧啶
  参考文献：
  名称：

  An Expeditious Route toward Pyrazine-Containing Nucleoside Analogues

  摘要：

  An improved and convenient methodology for the synthesis of asymmetrically substituted pyrazines starting from 3,5-dichloropyrazin-2(1H)-ones has been elaborated. Several nucleoside analogues have been synthesized containing the pyrazine core as the organic base coupled with the sugar via a triazole linkage. The beneficial effect of microwave irradiation throughout the sequence has been demonstrated.

  DOI：

  10.1021/jo102089h
• 作为产物：
  描述：

  2-巯基嘧啶 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以33%的产率得到2-[(4-methoxybenzyl)thio]pyrimidine
  参考文献：
  名称：

  Antimycobacterial Agents. 1. Thio Analogues of Purine

  摘要：

  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.

  DOI：

  10.1021/jm030389b

文献信息

• Lewis Acid Catalysed Chemoselective Amination of Alcohols Using Heterocyclic Thiones: An Avenue to Thiotetrazole Derivatives
  作者：Sudhamoyee Kataky、Pikumoni Boruah、Ashim J. Thakur

  DOI：10.1002/ejoc.202300515

  日期：2023.10.16

  Herein, the development of a Cu(OTf)2 catalysed chemoselective amination of alcohols using heterocyclic thiones is described. Notably, the method is additive, ligand or inert atmosphere free and shows good tolerance towards variety of alcohols and thiotetrazole derivatives affording good to excellent yields of the product.

  本文描述了使用杂环硫酮进行Cu(OTf) 2催化的醇的化学选择性胺化的开发。值得注意的是，该方法不含添加剂、配体或惰性气氛，并且对各种醇和硫代四唑衍生物表现出良好的耐受性，从而提供良好至优异的产物产率。
• 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.
• An Expeditious Route toward Pyrazine-Containing Nucleoside Analogues
  作者：Sachin G. Modha、Jalpa C. Trivedi、Vaibhav P. Mehta、Denis S. Ermolat’ev、Erik V. Van der Eycken

  DOI：10.1021/jo102089h

  日期：2011.2.4

  An improved and convenient methodology for the synthesis of asymmetrically substituted pyrazines starting from 3,5-dichloropyrazin-2(1H)-ones has been elaborated. Several nucleoside analogues have been synthesized containing the pyrazine core as the organic base coupled with the sugar via a triazole linkage. The beneficial effect of microwave irradiation throughout the sequence has been demonstrated.