1-(1-methyl-1H-pyrazol-3-yl)butan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-methyl-1H-pyrazol-3-yl)butan-1-one
• 英文别名: 1-(1-Methylpyrazol-3-yl)butan-1-one
• 化学式: C₈H₁₂N₂O
• 分子量: 152.196
• InChiKey: LWELVQYHGXKSOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  对氟碘苯 、 1-(1-methyl-1H-pyrazol-3-yl)butan-1-one 在 palladium diacetate 、 caesium carbonate 作用下， 以 均三甲苯 为溶剂， 反应 14.0h， 以43%的产率得到2-(4-fluorophenyl)-1-(1-methyl-1H-pyrazol-3-yl)butan-1-one
  参考文献：
  名称：

  Site‐Selective Pd‐Catalyzed C(sp ³ )−H Arylation of Heteroaromatic Ketones

  摘要：

  AbstractA ligand‐controlled site‐selective C(sp3)−H arylation of heteroaromatic ketones has been developed using Pd catalysis. The reaction occurred selectively at the α‐ or β‐position of the ketone side‐chain. The switch from α‐ to β‐arylation was realized by addition of a pyridone ligand. The α‐arylation process showed broad scope and high site‐ and chemoselectivity, whereas the β‐arylation was more limited. Mechanistic investigations suggested that α‐arylation occurs through C−H activation/oxidative addition/reductive elimination whereas β‐arylation involves desaturation and aryl insertion.

  DOI：

  10.1002/chem.202103467
• 作为产物：
  描述：

  1-甲基吡唑-3-甲酸 在 N,N'-羰基二咪唑 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 1-(1-methyl-1H-pyrazol-3-yl)butan-1-one
  参考文献：
  名称：

  Site‐Selective Pd‐Catalyzed C(sp ³ )−H Arylation of Heteroaromatic Ketones

  摘要：

  AbstractA ligand‐controlled site‐selective C(sp3)−H arylation of heteroaromatic ketones has been developed using Pd catalysis. The reaction occurred selectively at the α‐ or β‐position of the ketone side‐chain. The switch from α‐ to β‐arylation was realized by addition of a pyridone ligand. The α‐arylation process showed broad scope and high site‐ and chemoselectivity, whereas the β‐arylation was more limited. Mechanistic investigations suggested that α‐arylation occurs through C−H activation/oxidative addition/reductive elimination whereas β‐arylation involves desaturation and aryl insertion.

  DOI：

  10.1002/chem.202103467

文献信息

• Site‐Selective Pd‐Catalyzed C(sp ³ )−H Arylation of Heteroaromatic Ketones
  作者：Anton Kudashev、Olivier Baudoin

  DOI：10.1002/chem.202103467

  日期：2021.12.15

  AbstractA ligand‐controlled site‐selective C(sp3)−H arylation of heteroaromatic ketones has been developed using Pd catalysis. The reaction occurred selectively at the α‐ or β‐position of the ketone side‐chain. The switch from α‐ to β‐arylation was realized by addition of a pyridone ligand. The α‐arylation process showed broad scope and high site‐ and chemoselectivity, whereas the β‐arylation was more limited. Mechanistic investigations suggested that α‐arylation occurs through C−H activation/oxidative addition/reductive elimination whereas β‐arylation involves desaturation and aryl insertion.