2-benzyl-6-chloro-4-[2-furyl(hydroxy)methyl]pyridazin-3(2H)-one | 1316848-94-8

• 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: 2-benzyl-6-chloro-4-[2-furyl(hydroxy)methyl]pyridazin-3(2H)-one
• 英文别名: 2-Benzyl-6-chloro-4-[furan-2-yl(hydroxy)methyl]pyridazin-3-one
• CAS: 1316848-94-8
• 化学式: C₁₆H₁₃ClN₂O₃
• 分子量: 316.744
• InChiKey: UMRRVZLIYRKOFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  糠醛 、 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61%的产率得到2-benzyl-6-chloro-4-[2-furyl(hydroxy)methyl]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

文献信息

• Synthesis of Functionalized Pyridazin-3(2<i>H</i>)-ones via Selective Bromine–Magnesium Exchange and Lactam Directed Ortho C–H Magnesiation
  作者：Tom Verhelst、Jens Maes、Zuming Liu、Sergey Sergeyev、Bert U. W. Maes

  DOI：10.1021/jo201009m

  日期：2011.8.19

  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.