2,2-difluoro-N-phenyl-2-(thiophene-2-yl)acetamide | 1332344-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-difluoro-N-phenyl-2-(thiophene-2-yl)acetamide
• 英文别名: 2,2-difluoro-N-phenyl-2-(thiophen-2-yl)acetamide；2,2-difluoro-N-phenyl-2-thiophen-2-ylacetamide
• CAS: 1332344-65-6
• 化学式: C₁₂H₉F₂NOS
• 分子量: 253.272
• InChiKey: VDJLVDZAJPFTTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-噻吩乙酰氯 、 苯胺 在 吡啶 、 tin(II) trifluoromethanesulfonate 、 Selectfluor 、 四-(五氟苯)硼酸钾盐 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以42%的产率得到2,2-difluoro-N-phenyl-2-(thiophene-2-yl)acetamide
  参考文献：
  名称：

  Tricomponent Catalytic α,α-Difluorination of Acid Chlorides

  摘要：

  The selective alpha,alpha-difluorination of carbonyl compounds remains a challenge in modern organic synthesis; current methods often incorporate stepwise processes and/or harsh conditions, providing unsatisfactory mixtures of mono- and difluorinated products. In this communication, a practical, mild, and one-pot method for the selective alpha,alpha-difluorination of readily available acid chlorides is reported in which three separate catalysts act synergistically to form products in outstanding selectivity and fair to excellent yields.

  DOI：

  10.1021/ol2019295

文献信息

• A Chelating Nucleophile Plays a Starring Role: 1,8-Naphthyridine-Catalyzed Polycomponent α,α-Difluorination of Acid Chlorides
  作者：Andrew Griswold、Steven Bloom、Thomas Lectka

  DOI：10.1021/jo501534k

  日期：2014.10.17

  A dually activated ketene enolate, generated from an acid chloride, the unusual chelating nucleophile (1,8-naphthyridine), and a Lewis acid, reacts to afford a host of alpha,alpha-difluorinated products in the presence of a benchtop-stable fluorinating agent (Selectfluor). The use of this method to synthesize otherwise difficult to make products is highlighted along with computational and spectroscopic support for the proposed chelate.