N-(5-benzoylpyridin-2-yl)cyclopropanecarboxamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(5-benzoylpyridin-2-yl)cyclopropanecarboxamide
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: HAPMYSLWIAAYEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(5-iodopyridin-2-yl)cyclopropanecarboxamide 、 9-methyl-9H-fluorene-9-carbonyl chloride 、 苯硼酸 在 N,N-二异丙基乙胺 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 tri tert-butylphosphoniumtetrafluoroborate 、 potassium carbonate 、 palladium dichloride 作用下， 以70%的产率得到N-(5-benzoylpyridin-2-yl)cyclopropanecarboxamide
  参考文献：
  名称：

  An Air-Tolerant Approach to the Carbonylative Suzuki–Miyaura Coupling: Applications in Isotope Labeling

  摘要：

  Carbonylative Suzuki-Miyaura coupling conditions have been developed that proceed without the exclusion of oxygen and in the presence of nondegassed and nondried solvents. By adapting the method to a two-chamber setup, the direct handling of carbon monoxide, produced from stable CO precursors, is avoided. The protocol afforded the desired benzophenones with excellent functional group tolerance and in good yields. Substituting the CO precursor, in the CO-producing chamber, with its carbon-13 labeled version generated the corresponding carbon-13 labeled benzophenones. Finally, the developed system was applied in the synthesis and isotope labeling of two pharmaceuticals, nordazepam and Tricor.

  DOI：

  10.1021/jo401696c

文献信息

• An Air-Tolerant Approach to the Carbonylative Suzuki–Miyaura Coupling: Applications in Isotope Labeling
  作者：Andreas Ahlburg、Anders T. Lindhardt、Rolf. H. Taaning、Amalie E. Modvig、Troels Skrydstrup

  DOI：10.1021/jo401696c

  日期：2013.10.18

  Carbonylative Suzuki-Miyaura coupling conditions have been developed that proceed without the exclusion of oxygen and in the presence of nondegassed and nondried solvents. By adapting the method to a two-chamber setup, the direct handling of carbon monoxide, produced from stable CO precursors, is avoided. The protocol afforded the desired benzophenones with excellent functional group tolerance and in good yields. Substituting the CO precursor, in the CO-producing chamber, with its carbon-13 labeled version generated the corresponding carbon-13 labeled benzophenones. Finally, the developed system was applied in the synthesis and isotope labeling of two pharmaceuticals, nordazepam and Tricor.