1-(4-甲氧基苄基)-5-氯-3-甲氧基-6-(4-甲氧基苯基)吡嗪-2-(1H)-硫酮 | 1015075-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1-(4-甲氧基苄基)-5-氯-3-甲氧基-6-(4-甲氧基苯基)吡嗪-2-(1H)-硫酮
• 英文名称: 1-(4-methoxybenzyl)-5-chloro-3-methoxy-6-(4-methoxyphenyl)pyrazin-2-(1H)-thione
• 英文别名: 5-Chloro-3-methoxy-6-(4-methoxyphenyl)-1-[(4-methoxyphenyl)methyl]pyrazine-2-thione
• CAS: 1015075-04-3
• 化学式: C₂₀H₁₉ClN₂O₃S
• 分子量: 402.901
• InChiKey: NXEYEBRFLIVQNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-甲氧基苄基)-5-氯-3-甲氧基-6-(4-甲氧基苯基)吡嗪-2-(1H)-硫酮 、 碘甲烷 在 碘 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以71%的产率得到2-氯-6-甲氧基-3-(4-甲氧基苯基)-5-(甲硫基)吡嗪
  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-甲氧基-6-(4-甲氧基苯基)吡嗪-2-(1H)-酮 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以81%的产率得到1-(4-甲氧基苄基)-5-氯-3-甲氧基-6-(4-甲氧基苯基)吡嗪-2-(1H)-硫酮
  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

• 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.