1,6-dihydro-6-oxo-4-phenyl-[2,3']bipyridinyl-3-carboxylic acid ethyl ester | 1188531-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1,6-dihydro-6-oxo-4-phenyl-[2,3']bipyridinyl-3-carboxylic acid ethyl ester
• 英文别名: ethyl 6-oxo-4-phenyl-2-pyridin-3-yl-1H-pyridine-3-carboxylate
• CAS: 1188531-47-6
• 化学式: C₁₉H₁₆N₂O₃
• 分子量: 320.348
• InChiKey: PPTGTGUPUBAMDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氰基吡啶 、 溴乙酸乙酯 、 苯丙炔酸乙酯 在 甲烷磺酸 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以83%的产率得到1,6-dihydro-6-oxo-4-phenyl-[2,3']bipyridinyl-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  One-Pot Synthesis of 2-Pyridones via Chemo- and Regioselective Tandem Blaise Reaction of Nitriles with Propiolates

  摘要：

  The Blaise reaction intermediate, generated in situ from Reformatsky reagent and nitrile, reacted with propiolates in a chemo- and regioselective manner to afford 2-pyridone derivatives in good to excellent yields

  DOI：

  10.1021/jo901642t

文献信息

• One-Pot Synthesis of 2-Pyridones via Chemo- and Regioselective Tandem Blaise Reaction of Nitriles with Propiolates
  作者：Yu Sung Chun、Ka Yeon Ryu、Young Ok Ko、Joo Yeon Hong、Jongki Hong、Hyunik Shin、Sang-gi Lee

  DOI：10.1021/jo901642t

  日期：2009.10.2

  The Blaise reaction intermediate, generated in situ from Reformatsky reagent and nitrile, reacted with propiolates in a chemo- and regioselective manner to afford 2-pyridone derivatives in good to excellent yields
• Tandem Transformations of Nitriles into N-Heterocyclic Compounds by Electrophilic Trapping of Blaise Reaction Intermediates
  作者：Hyunik Shin、Sang-gi Lee、Ju Kim、Yu Chun

  DOI：10.1055/s-0031-1290814

  日期：2012.6

  Tandem transformations of nitriles into various N-heterocycles have been accomplished through the reaction of electrophiles with Blaise reaction intermediates formed in situ. The reaction of the Blaise reaction intermediates with propiolates gives 2-pyridones through consecutive C- and N-nucleophilic reactions. The tandem reactions of the Blaise reaction intermediate with 1,3-enynes proceed through C-nucleophilic addition followed by an electrocyclization-aromatization cascade to give pyridines. Exocyclic enamino esters can be prepared by transformations of omega-chloroalkyl nitriles through chemoselective intramolecular alkylation of the Blaise reaction intermediate. Palladium-catalyzed intramolecular arylations or copper-catalyzed intermolecular cross-coupling reactions of the Blaise reaction intermediate give a range of indole derivatives. Combinations of tandem alkylations and palladium-catalyzed couplings of the Blaise reaction intermediates of omega-chloroalkyl nitriles give N-fused indoles.