2-fluoro-2-nitro-1-phenylethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-fluoro-2-nitro-1-phenylethanone
• 化学式: C₈H₆FNO₃
• 分子量: 183.139
• InChiKey: UUWQMZYJJLNTJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲酰硝基甲烷 在 1-乙烯基-3-丁基咪唑氯盐 、 Selectfluor 作用下， 反应 10.0h， 以61%的产率得到2-fluoro-2-nitro-1-phenylethanone
  参考文献：
  名称：

  Mild and selective α-fluorination of carbonyl compounds (ketones, 1,3-diketones, β-ketoesters, α-nitroketones, and β-ketonitriles) with Selectfluor (F-TEDA-BF4) in imidazolium ILs [BMIM/PF6 or BMIM/NTf2] with Brønsted-acidic IL [PMIM(SO3H)/OTf] as promoter

  摘要：

  Structurally diverse ketones, 1,3-diketones, and beta-ketoesters, were selectively monofluorinated with Selectfluor (F-TEDA-BF4) (1 equiv) in [BMIM][PF6] as solvent and [PMIM(SO3H)][OTf] as promoter under mild conditions. In selected cases, the monofluorinated products were transformed to the gem-difluoro derivatives by employing an additional equivalent of Selectfluor, and gem-difluoro-derivatives were synthesized directly from the substrates by employing 2 equiv of Selectfluor. The method was extended to monofluorination of representative alpha-nitroketones and beta-ketonitriles using [BMIM][NTf2] without the need for promoters. The described method offers the added advantage of recycling and reuse of the IL solvent.

  DOI：

  10.1016/j.tetlet.2015.07.084

文献信息

• Convenient fluorination of nitro and nitrile compounds with Selectfluor
  作者：Weimin Peng、Jean’ne M. Shreeve

  DOI：10.1016/j.tetlet.2005.05.056

  日期：2005.7

  A variety of nitro and nitrile compounds were fluorinated in good yields by Selectfluor under mild conditions. For these transformations to be successful, it is crucial to select proper amounts of an appropriate base as a function of the properties of the substrate and also to use Selectfluor only as required. (c) 2005 Elsevier Ltd. All rights reserved.
• US4880814A
  申请人：——

  公开号：US4880814A

  公开（公告）日：1989-11-14
• Mild and selective α-fluorination of carbonyl compounds (ketones, 1,3-diketones, β-ketoesters, α-nitroketones, and β-ketonitriles) with Selectfluor (F-TEDA-BF4) in imidazolium ILs [BMIM/PF6 or BMIM/NTf2] with Brønsted-acidic IL [PMIM(SO3H)/OTf] as promoter
  作者：A. Srinivas Reddy、Kenneth K. Laali

  DOI：10.1016/j.tetlet.2015.07.084

  日期：2015.10

  Structurally diverse ketones, 1,3-diketones, and beta-ketoesters, were selectively monofluorinated with Selectfluor (F-TEDA-BF4) (1 equiv) in [BMIM][PF6] as solvent and [PMIM(SO3H)][OTf] as promoter under mild conditions. In selected cases, the monofluorinated products were transformed to the gem-difluoro derivatives by employing an additional equivalent of Selectfluor, and gem-difluoro-derivatives were synthesized directly from the substrates by employing 2 equiv of Selectfluor. The method was extended to monofluorination of representative alpha-nitroketones and beta-ketonitriles using [BMIM][NTf2] without the need for promoters. The described method offers the added advantage of recycling and reuse of the IL solvent.