2-benzyl-6-chloro-4-(methylthio)pyridazin-3(2H)-one | 1316848-92-6

• 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-benzyl-6-chloro-4-(methylthio)pyridazin-3(2H)-one
• 英文别名: 2-Benzyl-6-chloro-4-methylsulfanylpyridazin-3-one
• CAS: 1316848-92-6
• 化学式: C₁₂H₁₁ClN₂OS
• 分子量: 266.751
• InChiKey: HTFQBGHUVZEMKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基硫代磺酸甲酯 、 2-benzyl-6-chloropyridazin-3(2H)-one 在 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.25h， 以66%的产率得到2-benzyl-6-chloro-4-(methylthio)pyridazin-3(2H)-one
  参考文献：
  名称：

  Synthesis of Functionalized Pyridazin-3(2H)-ones via Selective Bromine–Magnesium Exchange and Lactam Directed Ortho C–H Magnesiation

  摘要：

  Selective bromine magnesium exchange on 2-benzyl-5-bromo-4-methoxypyridazin-3(2H)-one could be achieved when MesMgBr was used as reagent. With more nucleophilic RMgCl species (R = Bu, i-Pr, Ph) both nucleophilic addition-elimination at C-4 and bromine-magnesium exchange at C-5 occurred. In 2-benzyl-5-bromopyridazin-3(2H)-one, which does not contain a substituent at C-4, addition could not be suppressed. Less nucleophilic Mg amides (TMPMgCl center dot LiCl) allowed regioselective C-H magnesiation at the C-4 position in such substrates, as exemplified for 2-benzyl-5-chloro- and 2-benzyl-6-chloropyridazin-3(2H)-one. Quenching of the magnesiated pyridazinones with electrophiles gives access to a variety of hitherto unknown pyridazin-3(2H)-one derivatives.

  DOI：

  10.1021/jo201009m