2-[4-(Trifluoromethoxy)phenyl]-1H-indole-3-carboxylic acid ethyl ester | 1397284-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-[4-(Trifluoromethoxy)phenyl]-1H-indole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2-[4-(trifluoromethoxy)phenyl]-1H-indole-3-carboxylate
• CAS: 1397284-82-0
• 化学式: C₁₈H₁₄F₃NO₃
• 分子量: 349.309
• InChiKey: CLNICGCYIDZZTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Brom-<2-brom-phenyl>-essigsaeure-ethylester 、 4-三氟甲氧基苯腈 在 甲烷磺酸 、 锌 、 四(三苯基膦)钯 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 以72%的产率得到2-[4-(Trifluoromethoxy)phenyl]-1H-indole-3-carboxylic acid ethyl ester
  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 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.