5-iodo-3-methyl-2-(methylthio)pyrazine | 1015075-19-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-iodo-3-methyl-2-(methylthio)pyrazine
• 英文别名: 5-Iodo-3-methyl-2-methylsulfanylpyrazine
• CAS: 1015075-19-0
• 化学式: C₆H₇IN₂S
• 分子量: 266.105
• InChiKey: DFFHXVJVLFKYKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-iodo-3-methyl-2-(methylthio)pyrazine 、 4-乙氧羰基苯硼酸 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.17h， 以99%的产率得到ethyl-4-(6-methyl-5-(methylthio)pyrazin-2-yl)benzoate
  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
• 作为产物：
  描述：

  1-(4-甲氧基苄基)-5-氯-3-甲基吡嗪-2-硫酮 、 碘甲烷 在 碘 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以67%的产率得到5-iodo-3-methyl-2-(methylthio)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