2,2-difluoro-1-phenyl-2-(phenylmethanesulfonyl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-difluoro-1-phenyl-2-(phenylmethanesulfonyl)ethanone
• 英文别名: 2-(benzylsulfonyl)-2,2-difluoro-1-phenylethanone；2-Benzylsulfonyl-2,2-difluoro-1-phenylethanone
• 化学式: C₁₅H₁₂F₂O₃S
• 分子量: 310.321
• InChiKey: SLXXESMDFOSWCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-苯基-2-(苯基甲硫基)乙酮 在 Selectfluor 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 2,2-difluoro-1-phenyl-2-(phenylmethanesulfonyl)ethanone
  参考文献：
  名称：

  An efficient fluorination of β-ketosulfones promoted by a room-temperature ionic liquid at ambient conditions under ultrasound irradiation using Selectfluor™ F-TEDA-BF4

  摘要：

  The fluorination reaction involving a beta-ketosulfones by Selectfluor (TM) was efficiently promoted by the ionic liquid, [Hbim]BF4 (IL) as a reaction medium with methanol as co-solvent at room temperature under ultrasonic irradiation to afford the corresponding mono and difluoro-beta-ketosulfones in excellent yields. The advantages of this method include among others the use of a recyclable, non-volatile ionic liquid, which promotes this protocol under room temperature without the requirement of any added catalyst under ultrasonic irradiation. (C) 2010 Mohammad Reza Poor Heravi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2010.06.030

文献信息

• An Efficient Preparation of New Sulfonyl Fluorides and Lithium Sulfonates
  作者：Fabien Toulgoat、Bernard. R. Langlois、Maurice Médebielle、Jean-Yves Sanchez

  DOI：10.1021/jo701318n

  日期：2007.11.1

  polyfluoroalkanesulfonyl fluorides is reported. This method, based on the synthesis of polyfluoroalkyl trimethyl silanes (precursors of polyfluoroalkylsulfinates) as intermediates, allows the successive transformations to be carried out in one pot. Moreover, these sulfonyl fluorides can be obtained from the corresponding sulfinates by electrophilic fluorination. This original approach avoids isolation and purification

  报道了几种多氟链烷磺酰氟的有效制备方法。该方法基于多氟烷基三甲基硅烷（多氟烷基亚磺酸盐的前体）作为中间体的合成，可以在一个罐中进行连续的转化。而且，这些磺酰氟可以通过亲电氟化从相应的亚磺酸盐获得。这种原始方法避免了某些热或水解不稳定中间体的分离和纯化。因此，已经从卤代二氟甲基化的前体RCF 2 X（X = F，Br; R = ArC（O），ArS（O）n（CF 2）m ; n = 0，1，2; m制备了一系列新的磺酰氟。 = 1、2），并已转化为相应的磺酸锂，它们有潜力用作锂电池的电解质。
• α-Fluorination of β-ketosulfones by Selectfluor™ F–TEDA–BF4
  作者：Hossein Loghmani-Khouzani、Mohammad R. Poorheravi、Majid M.M. Sadeghi、Lorenzo Caggiano、Richard F.W. Jackson

  DOI：10.1016/j.tet.2008.05.034

  日期：2008.7

  Attempted fluorination of β-ketosulfides using Selectfluor™ resulted only in the isolation of the corresponding diaryl disulfides, presumed to arise by decomposition of an unstable fluorinated intermediate. However, fluorination of β-ketosulfones using Selectfluor™ under anhydrous conditions does allow the isolation of both mono-and difluorinated products in moderate to good yields.

  使用Selectfluor™尝试对β-酮硫醚进行氟化，仅导致了相应的二芳基二硫化物的分离，推测是由于不稳定的氟化中间体的分解而引起的。但是，在无水条件下使用Selectfluor™对β-酮砜进行氟化，确实能够以中等到良好的产率分离出单氟化和二氟化的产物。