4-phenyl-1-(pyridin-2-yl)butan-1-one | 56956-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-phenyl-1-(pyridin-2-yl)butan-1-one
• 英文别名: 4-Phenyl-1-pyridin-2-ylbutan-1-one
• CAS: 56956-52-6
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: JZWMDIJMRQFVIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyl-1-(pyridin-2-yl)butan-1-one 、 对氟碘苯 在 palladium diacetate 、 caesium carbonate 作用下， 以 均三甲苯 为溶剂， 反应 14.0h， 以80%的产率得到2-(4-fluorophenyl)-4-phenyl-1-(pyridin-2-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：

  2-吡啶甲酸 、 2,2'-(3-phenylpropane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 在 甲基锂 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 8.08h， 以64%的产率得到4-phenyl-1-(pyridin-2-yl)butan-1-one
  参考文献：
  名称：

  通过羧酸脱氧烯醇化使α-单硼碳烷基双官能化

  摘要：

  通过与羧酸的脱氧烯醇化反应，开发了1,1-二硼烷基烷烃的双官能团。MeLi激活1,1-二硼烷基烷烃生成α-单硼烷基碳负离子。原位红外光谱表明，在添加活化剂之前，羧酸和1,1-二硼烷基烷烃之间存在相互作用。从掩蔽形式释放活性α-单硼烷基碳负离子是其与羧酸盐反应以提供烯醇盐类所必需的。用各种亲电试剂对烯醇盐物种进行亲电捕获，实现了1,1-二硼烷基烷烃的双重功能化，从而提供了多种α-单，二和三取代的酮。

  DOI：

  10.1002/anie.201801679

文献信息

• Dual Functionalization of α‐Monoboryl Carbanions through Deoxygenative Enolization with Carboxylic Acids
  作者：Wei Sun、Lu Wang、Chungu Xia、Chao Liu

  DOI：10.1002/anie.201801679

  日期：2018.5.4

  1‐diborylalkanes through deoxygenative enolization with carboxylic acids was developed. 1,1‐Diborylalkanes were activated by MeLi to generate α‐monoboryl carbanions. In situ IR spectroscopy indicated an interaction between carboxylic acid and 1,1‐diborylalkane before addition of the activation reagent. Release of the active α‐monoboryl carbanion from the masked form was necessary for its reaction with carboxylate

  通过与羧酸的脱氧烯醇化反应，开发了1,1-二硼烷基烷烃的双官能团。MeLi激活1,1-二硼烷基烷烃生成α-单硼烷基碳负离子。原位红外光谱表明，在添加活化剂之前，羧酸和1,1-二硼烷基烷烃之间存在相互作用。从掩蔽形式释放活性α-单硼烷基碳负离子是其与羧酸盐反应以提供烯醇盐类所必需的。用各种亲电试剂对烯醇盐物种进行亲电捕获，实现了1,1-二硼烷基烷烃的双重功能化，从而提供了多种α-单，二和三取代的酮。
• 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.