1-[5-methoxy-2-(2-pyridinyl)phenyl]-1-propanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[5-methoxy-2-(2-pyridinyl)phenyl]-1-propanone
• 英文别名: 1-(5-methoxy-2-(pyridin-2-yl)phenyl)propan-1-one；1-(5-Methoxy-2-pyridin-2-ylphenyl)propan-1-one；1-(5-methoxy-2-pyridin-2-ylphenyl)propan-1-one
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: IDCPUEWODYWRQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴吡啶 在 叔丁基过氧化氢 、 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1-[5-methoxy-2-(2-pyridinyl)phenyl]-1-propanone
  参考文献：
  名称：

  Direct Carbo-Acylation Reactions of 2-Arylpyridines with α-Diketones via Pd-Catalyzed C–H Activation and Selective C(sp2)–C(sp2) Cleavage

  摘要：

  An efficient carbo-acylation reaction of 2-arylpyridines with alpha-diketones via Pd-catalyzed C-H bond activation and C-C bond cleavage in the presence of TBHP was developed that generated aryl ketones in good yields. The highly selective formation of aryl ketones was observed when 2-arylpyridines reacted with aromatic/aliphatic alpha-diketones.

  DOI：

  10.1021/ol3020557

文献信息

• Rhodium-catalyzed C-H–CO–olefin coupling reactions — A chelation-assisted direct carbonylation at the ortho C—H bond in the benzene ring of 2-arylpyridines
  作者：Naoto Chatani、Takeshi Uemura、Taku Asaumi、Yutaka Ie、Fumitoshi Kakiuchi、Shinji Murai

  DOI：10.1139/v05-077

  日期：2005.6.1

  The reaction of 2-arylpyridines with ethylene and carbon monoxide in the presence of a catalytic amount of Rh₄(CO)₁₂ results in selective carbonylation at the ortho C—H bond. The reaction is heavily dependent on the solvents used, with DMA (N,N-dimethylacetamide) being the solvent of choice. Steric factors are also important determinants of the efficiency of the reaction.Key words: C—H bond activation, carbonylation, chelation, rhodium, carbon monoxide.

  2-芳基吡啶与乙烯和一定量的Rh4(CO)12在溶剂DMA（N,N-二甲基乙酰胺）存在下发生选择性的醛基化反应，主要在邻位C-H键上进行。该反应对所使用的溶剂非常依赖，DMA是首选溶剂。此外，立体因素也是影响反应效率的重要因素。关键词：C-H键活化，醛基化，螯合，铑，一氧化碳。
• Ru/C-Catalyzed Carbonylation at <i>ortho</i>-C-H Bonds in 2-Phenylpyridines
  作者：Naoto Chatani、Shinya Imoto、Takeshi Uemura、Fumitoshi Kakiuchi

  DOI：10.1055/s-2006-958451

  日期：2007.1

  Ru/C also exhibits catalytic activity for carbonylation at ortho-C-H bonds in 2-phenylpyridines.

  Ru/C 也显示出对 2-苯基吡啶中 ortho-C-H 键的羰基化催化活性。
• Direct Carbo-Acylation Reactions of 2-Arylpyridines with α-Diketones via Pd-Catalyzed C–H Activation and Selective C(sp2)–C(sp2) Cleavage
  作者：Wei Zhou、Hongji Li、Lei Wang

  DOI：10.1021/ol3020557

  日期：2012.9.7

  An efficient carbo-acylation reaction of 2-arylpyridines with alpha-diketones via Pd-catalyzed C-H bond activation and C-C bond cleavage in the presence of TBHP was developed that generated aryl ketones in good yields. The highly selective formation of aryl ketones was observed when 2-arylpyridines reacted with aromatic/aliphatic alpha-diketones.