2-chloro-6-[(1,1-dimethylethyl)sulfanyl]pyrazine | 1094787-68-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-chloro-6-[(1,1-dimethylethyl)sulfanyl]pyrazine
• 英文别名: 2-Tert-butylsulfanyl-6-chloropyrazine
• CAS: 1094787-68-4
• 化学式: C₈H₁₁ClN₂S
• 分子量: 202.708
• InChiKey: WEDFHTTVEAHDIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-chloro-6-[(1,1-dimethylethyl)sulfanyl]pyrazine 在 正丁基锂 、 sodium hydrosulfide hydrate 、 palladium 10% on activated carbon 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 14.0h， 生成 3-(1,1-dimethylethyl)sulfanyl-7-phenylthieno[2,3-b]pyrazine
  参考文献：
  名称：

  A Convenient Two-Step Synthesis of 7-Aryl-6,7-dihydrothieno[2,3-b]pyrazines from Aryl(3-chloropyrazin-2-yl)methanones

  摘要：

  An efficient method for the preparation of 7-aryl-6,7-dihydrothieno[2,3-b]pyrazines (3) under mild conditions has been developed. The reaction of aryl(3-chloropyrazin-2-yl)methanones (1), derived from commercially available 2-chloropyrazine, with methylenetriphenylphosphorane in THF at room temperature gave the corresponding 2-(1-arylethenyl)-3-chloropyrazines (2), which were treated with NaSH center dot nH(2)O in DMF at room temperature to lead to the desired products (3) in acceptable yields. These products are dehydrogenated with air in refluxing toluene in the presence of a catalytic amount of Pd/C to yield the corresponding 7-arylthieno [2,3-b]pyrazines (4).

  DOI：

  10.3987/com-13-12728
• 作为产物：
  描述：

  2,6-二氯吡嗪 、 叔丁基硫醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.42h， 以62%的产率得到2-chloro-6-[(1,1-dimethylethyl)sulfanyl]pyrazine
  参考文献：
  名称：

  A Convenient Two-Step Synthesis of 7-Aryl-6,7-dihydrothieno[2,3-b]pyrazines from Aryl(3-chloropyrazin-2-yl)methanones

  摘要：

  An efficient method for the preparation of 7-aryl-6,7-dihydrothieno[2,3-b]pyrazines (3) under mild conditions has been developed. The reaction of aryl(3-chloropyrazin-2-yl)methanones (1), derived from commercially available 2-chloropyrazine, with methylenetriphenylphosphorane in THF at room temperature gave the corresponding 2-(1-arylethenyl)-3-chloropyrazines (2), which were treated with NaSH center dot nH(2)O in DMF at room temperature to lead to the desired products (3) in acceptable yields. These products are dehydrogenated with air in refluxing toluene in the presence of a catalytic amount of Pd/C to yield the corresponding 7-arylthieno [2,3-b]pyrazines (4).

  DOI：

  10.3987/com-13-12728