3-methoxy-2-(methylthio)-5-(2-phenylethynyl)pyrazine | 1015075-44-1

• 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: 3-methoxy-2-(methylthio)-5-(2-phenylethynyl)pyrazine
• 英文别名: 3-Methoxy-2-methylsulfanyl-5-(2-phenylethynyl)pyrazine；3-methoxy-2-methylsulfanyl-5-(2-phenylethynyl)pyrazine
• CAS: 1015075-44-1
• 化学式: C₁₄H₁₂N₂OS
• 分子量: 256.328
• InChiKey: UMGIJXVFPMNBMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  3-methoxy-2-(methylthio)-5-(2-phenylethynyl)pyrazine 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 以45%的产率得到3-methoxy-2,5-bis(2-phenylethynyl)pyrazine
  参考文献：
  名称：

  钯催化的（杂）芳基硫醚与末端炔烃的钯催化脱硫Sonogashira型交叉偶联。

  摘要：

  由相应的5-氯-3-（苯基硫烷基）吡嗪-2（1H）-酮合成取代的5-氯-3-炔基吡嗪酮类化合物，说明了空前的脱硫Sonogashira型交叉偶联方案。该方法的适用范围扩展到固相连接的吡嗪-2（1H）-酮以及一些恶嗪酮，吡嗪和苯基硫代酯。

  DOI：

  10.1021/ol800054b
• 作为产物：
  描述：

  5-chloro-3-methoxy-2-(methylthio)pyrazine 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 四丁基溴化铵 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以69%的产率得到3-methoxy-2-(methylthio)-5-(2-phenylethynyl)pyrazine
  参考文献：
  名称：

  A Novel and Versatile Entry to Asymmetrically Substituted Pyrazines

  摘要：

  A novel and convenient procedure for the synthesis of asymmetrically tri- and tetrasubstituted pyrazines starting from para-methoxybenzyl-protected 3,5-dichloro-2(1H)-pyrazinones was elaborated. The key step is the conversion of the intermediate para-methoxybenzyl-protected thiopyrazinone upon treatment with MeI/I-2, into a pyrazine, rendering the chlorine in the C5-position susceptible to substitution. This approach entails the orthogonal introduction of the four substituents of the pyrazine scaffold. The application of microwave irradiation during different steps of the sequence has been shown to be highly valuable for speeding up reactions.

  DOI：

  10.1021/jo702656v

文献信息

• The First Palladium-Catalyzed Desulfitative Sonogashira-Type Cross-Coupling of (Hetero)aryl Thioethers with Terminal Alkynes
  作者：Vaibhav Pravinchandra Mehta、Anuj Sharma、Erik Van der Eycken

  DOI：10.1021/ol800054b

  日期：2008.3.1

  An unprecedented desulfitative Sonogashira-type cross-coupling protocol is exemplified by the synthesis of substituted 5-chloro-3-alkynylpyrazinones from the corresponding 5-chloro-3-(phenylsulfanyl) pyrazin-2(1H)-ones. The applicability of the method is extended to solid-phase linked pyrazin-2(1H)-ones as well as to some oxazinones, pyrazines, and phenyl thioesters.

  由相应的5-氯-3-（苯基硫烷基）吡嗪-2（1H）-酮合成取代的5-氯-3-炔基吡嗪酮类化合物，说明了空前的脱硫Sonogashira型交叉偶联方案。该方法的适用范围扩展到固相连接的吡嗪-2（1H）-酮以及一些恶嗪酮，吡嗪和苯基硫代酯。
• A Novel and Versatile Entry to Asymmetrically Substituted Pyrazines
  作者：Vaibhav Pravinchandra Mehta、Anuj Sharma、Kristof Van Hecke、Luc Van Meervelt、Erik Van der Eycken

  DOI：10.1021/jo702656v

  日期：2008.3.1

  A novel and convenient procedure for the synthesis of asymmetrically tri- and tetrasubstituted pyrazines starting from para-methoxybenzyl-protected 3,5-dichloro-2(1H)-pyrazinones was elaborated. The key step is the conversion of the intermediate para-methoxybenzyl-protected thiopyrazinone upon treatment with MeI/I-2, into a pyrazine, rendering the chlorine in the C5-position susceptible to substitution. This approach entails the orthogonal introduction of the four substituents of the pyrazine scaffold. The application of microwave irradiation during different steps of the sequence has been shown to be highly valuable for speeding up reactions.