[difluoro(4-fluorophenylsulfanyl)methyl]trimethylsilane

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: [difluoro(4-fluorophenylsulfanyl)methyl]trimethylsilane
• 英文别名: [Difluoro-(4-fluorophenyl)sulfanylmethyl]-trimethylsilane
• 化学式: C₁₀H₁₃F₃SSi
• 分子量: 250.36
• InChiKey: DAMUMTSHLPDHRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [difluoro(4-fluorophenylsulfanyl)methyl]trimethylsilane 在 fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 (4-fluorophenyl)(difluoromethyl)sulfane
  参考文献：
  名称：

  Direct S-difluoromethylation of thiols using the Ruppert–Prakash reagent

  摘要：

  Direct S-difluoromethylation of aryl and aliphatic thiols using the Ruppert-Prakash reagent is demonstrated. The reaction produces trimethylsilyldifluoromethyl sulfides, which upon cleavage with fluoride produces the difluoromethyl sulfides. The key reaction features are the use of relatively inexpensive and commercially available starting materials, shorter reaction times, ambient temperatures, easy reaction procedure, and selective S-difluoromethylation in the presence of-OH, -NH2 and -CO2H functional groups. Furthermore, one-pot arylthiodifluoromethyl transfer to PhCHO is also demonstrated. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.09.011
• 作为产物：
  描述：

  对氟苯硫酚 、 (三氟甲基)三甲基硅烷 在 lithium tetrafluoroborate 、 lithium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 [difluoro(4-fluorophenylsulfanyl)methyl]trimethylsilane
  参考文献：
  名称：

  Direct S-difluoromethylation of thiols using the Ruppert–Prakash reagent

  摘要：

  Direct S-difluoromethylation of aryl and aliphatic thiols using the Ruppert-Prakash reagent is demonstrated. The reaction produces trimethylsilyldifluoromethyl sulfides, which upon cleavage with fluoride produces the difluoromethyl sulfides. The key reaction features are the use of relatively inexpensive and commercially available starting materials, shorter reaction times, ambient temperatures, easy reaction procedure, and selective S-difluoromethylation in the presence of-OH, -NH2 and -CO2H functional groups. Furthermore, one-pot arylthiodifluoromethyl transfer to PhCHO is also demonstrated. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.09.011

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。
• Direct S-difluoromethylation of thiols using the Ruppert–Prakash reagent
  作者：G.K. Surya Prakash、Sankarganesh Krishnamoorthy、Sayan Kar、George A. Olah

  DOI：10.1016/j.jfluchem.2015.09.011

  日期：2015.12

  Direct S-difluoromethylation of aryl and aliphatic thiols using the Ruppert-Prakash reagent is demonstrated. The reaction produces trimethylsilyldifluoromethyl sulfides, which upon cleavage with fluoride produces the difluoromethyl sulfides. The key reaction features are the use of relatively inexpensive and commercially available starting materials, shorter reaction times, ambient temperatures, easy reaction procedure, and selective S-difluoromethylation in the presence of-OH, -NH2 and -CO2H functional groups. Furthermore, one-pot arylthiodifluoromethyl transfer to PhCHO is also demonstrated. (C) 2015 Elsevier B.V. All rights reserved.