N-{2-[(4-acetylphenyl)ethynyl]-4,6-difluorophenyl}-2,2,2-trifluoroacetamide | 1224449-73-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{2-[(4-acetylphenyl)ethynyl]-4,6-difluorophenyl}-2,2,2-trifluoroacetamide
• 英文别名: N-[2-[2-(4-acetylphenyl)ethynyl]-4,6-difluorophenyl]-2,2,2-trifluoroacetamide
• CAS: 1224449-73-3
• 化学式: C₁₈H₁₀F₅NO₂
• 分子量: 367.275
• InChiKey: OWHRKEKEKUVOSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-{2-[(4-acetylphenyl)ethynyl]-4,6-difluorophenyl}-2,2,2-trifluoroacetamide 、 1-(4-喹啉基)甲胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三苯胂 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以72%的产率得到2-[2-(4-acetylphenyl)-5,7-difluoro-1H-indol-3-yl]cyclohex-2-en-1-one
  参考文献：
  名称：

  3-(2-Alken-1-one-2-yl)indoles through the palladium-catalyzed reaction of 2-alkynyltrifluoroacetanilides with cyclic α-iodoenones

  摘要：

  alpha-Iodoenones can be efficiently employed as organic electrophiles in the Pd-catalyzed synthesis of 2, 3-disubstituted indoles from 2-alkynyltrifluoroacetanilides. Best results were obtained using the weak ligand As(Ph)(3). The methodology reported provides an efficient entry to indoles bearing a 2-alkenon-2-yl moiety linked in the 3-position, that possesses a scarcely reported substitution pattern. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.096
• 作为产物：
  描述：

  、 三氟乙酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-{2-[(4-acetylphenyl)ethynyl]-4,6-difluorophenyl}-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  3-(2-Alken-1-one-2-yl)indoles through the palladium-catalyzed reaction of 2-alkynyltrifluoroacetanilides with cyclic α-iodoenones

  摘要：

  alpha-Iodoenones can be efficiently employed as organic electrophiles in the Pd-catalyzed synthesis of 2, 3-disubstituted indoles from 2-alkynyltrifluoroacetanilides. Best results were obtained using the weak ligand As(Ph)(3). The methodology reported provides an efficient entry to indoles bearing a 2-alkenon-2-yl moiety linked in the 3-position, that possesses a scarcely reported substitution pattern. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.096

文献信息

• A Concise One-Pot Approach to the Synthesis of 4-(1H-Indol-3-yl)quinolines
  作者：Fabio Marinelli、Antonio Arcadi、Marco Chiarini、Silvia Picchini

  DOI：10.1055/s-0031-1289589

  日期：2011.12

  An operationally simple procedure, involving conjugate addition of NaI to β-(2-aminophenyl)-α,β-ynones/cyclization/Pd-catalyzed reaction with 2-alkynyl-trifluoroacetanilides, afforded 4-(1H-indol-3-yl)quinolines. The whole process was carried out in the same flask, without any intermediate work-up and using ethanol as solvent. annulation - palladium - quinolines - indoles - heterocycles - one-pot reaction

  一个操作简单的过程，涉及将NaI与2-炔基-三氟乙酰苯胺共轭加成至β-（2-氨基苯基）-α，β-炔酮/环化/ Pd催化的反应，得到4-（1 H-吲哚-3-基）喹啉。整个过程在同一烧瓶中进行，无需任何中间处理，并使用乙醇作为溶剂。 环化-钯-喹啉-吲哚-杂环-一锅反应
• 3-(2-Alken-1-one-2-yl)indoles through the palladium-catalyzed reaction of 2-alkynyltrifluoroacetanilides with cyclic α-iodoenones
  作者：Antonio Arcadi、Roberto Cianci、Giovanni Ferrara、Fabio Marinelli

  DOI：10.1016/j.tet.2010.01.096

  日期：2010.3

  alpha-Iodoenones can be efficiently employed as organic electrophiles in the Pd-catalyzed synthesis of 2, 3-disubstituted indoles from 2-alkynyltrifluoroacetanilides. Best results were obtained using the weak ligand As(Ph)(3). The methodology reported provides an efficient entry to indoles bearing a 2-alkenon-2-yl moiety linked in the 3-position, that possesses a scarcely reported substitution pattern. (C) 2010 Elsevier Ltd. All rights reserved.