ethyl 2-[4-(3-ethoxycarbonyl-6-oxo-6-phenyl-1,6-dihydro-pyridin-2-yl)-phenyl]-4-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylate | 1346263-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 2-[4-(3-ethoxycarbonyl-6-oxo-6-phenyl-1,6-dihydro-pyridin-2-yl)-phenyl]-4-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylate
• 英文别名: ethyl 2-[4-(3-ethoxycarbonyl-6-oxo-4-phenyl-1H-pyridin-2-yl)phenyl]-4-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylate
• CAS: 1346263-81-7
• 化学式: C₃₃H₃₂N₂O₅
• 分子量: 536.627
• InChiKey: KRMNBXIMZDTQCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对苯二腈 、 1-乙炔基环己烷 、 苯丙炔酸乙酯 在 锌 作用下， 以 1,4-二氧六环 为溶剂， 以39%的产率得到ethyl 2-[4-(3-ethoxycarbonyl-6-oxo-6-phenyl-1,6-dihydro-pyridin-2-yl)-phenyl]-4-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Tandem Transformations of Nitriles into N-Heterocyclic Compounds by Electrophilic Trapping of Blaise Reaction Intermediates

  摘要：

  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.

  DOI：

  10.1055/s-0031-1290814

文献信息

• Tandem One-Pot Synthesis of Polysubstituted Pyridines Using the Blaise Reaction Intermediate and 1,3-Enynes
  作者：Yu Sung Chun、Jun Hee Lee、Ju Hyun Kim、Young Ok Ko、Sang-gi Lee

  DOI：10.1021/ol202691b

  日期：2011.12.16

  method for the construction of a pyridine moiety with selective control of substitution patterns has been developed through the sequential reactions of nitrile with a Reformatsky reagent and 1,3-enyne involving regio- and chemoselective addition of the Blaise reaction intermediate to 1,3-enyne, followed by isomerization, cyclization, and an aromatization cascade.

  通过腈与Reformatsky试剂和1,3-烯炔的顺序反应（涉及将Blaise反应中间体与Blaise的区域和化学选择性加成），开发了一种具有选择性控制取代模式的吡啶结构的串联一锅法。 1,3-烯炔，然后进行异构化，环化和芳构化级联。