pentafluorobenzensulfonyl fluoride | 36650-04-1

• 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: pentafluorobenzensulfonyl fluoride
• 英文别名: 2,3,4,5,6-pentafluorobenzenesulfonyl fluoride；Pentafluorobenzene sulphonyl fluoride；pentafluorobenzenesulphonyl fluoride；pentafluorobenzenesulfonyl fluoride；Pentafluorbenzolsulfonsaeure-fluorid；(Pentafluorphenyl)sulfonylfluorid
• CAS: 36650-04-1
• 化学式: C₆F₆O₂S
• 分子量: 250.121
• InChiKey: IIIRAVUZGLMAHO-UHFFFAOYSA-N

物化性质

• 沸点：
  55-57 °C(Press: 10 Torr)
• 密度：
  1.771±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  五氟苯 、 pentafluorobenzensulfonyl fluoride 以15%的产率得到bis(pentafluorophenyl) sulphone
  参考文献：
  名称：

  Furin, G. G.; Yakobson, G. G., Izvestiya Sibirskogo Otdeleniya Akademii Nauk SSSR, Seriya Khimicheskikh Nauk

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,5,6-五氟苯磺酰氯 在 potassium hydrogen difluoride 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以72%的产率得到pentafluorobenzensulfonyl fluoride
  参考文献：
  名称：

  PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent

  摘要：

  We report an inexpensive, thermally stable deoxyfluorination reagent that fluorinates a broad range Of alcohols without substantial formation of elimination side products. This combination of selectivity; safety, and economic viability enables,deoxyfluorination on preparatory scale. We employ the [F-18]-labeled reagent in the first example of a no-carrier-added deoxy-radiofluorination:

  DOI：

  10.1021/jacs.5b06307

文献信息

• Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride
  作者：Gabriele Laudadio、Aloisio de A. Bartolomeu、Lucas M. H. M. Verwijlen、Yiran Cao、Kleber T. de Oliveira、Timothy Noël

  DOI：10.1021/jacs.9b06126

  日期：2019.7.31

  Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based “click chemistry” is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl

  磺酰氟是具有多种应用价值的合成基序，其中基于硫 (VI) 氟化物交换的“点击化学”是目前最突出的。因此，开发新的和有效的合成方法来访问这些官能团是非常有趣的。在此，我们报告了一种温和且环境友好的电化学方法，使用硫醇或二硫化物作为广泛可用的起始材料，结合 KF 作为廉价、丰富和安全的氟化物来源来制备磺酰氟。不需要额外的氧化剂或额外的催化剂，由于反应条件温和，反应显示出广泛的底物范围，包括各种烷基、苄基、芳基和杂芳基硫醇或二硫化物。
• SULFONAMIDE-BASED ORGANOCATALYSTS AND METHOD FOR THEIR USE
  申请人：Carter Rich Garrett

  公开号：US20100184986A1

  公开（公告）日：2010-07-22

  Organocatalysts, particularly proline sulfonamide organocatalysts, having a first general formula as follows are disclosed. Embodiments of a method for using these organocatalysts also are disclosed. The method comprises providing a disclosed organocatalyst, and performing a reaction, often an enantioselective or diastereoselective reaction, using the organocatalyst. Solely by way of example, disclosed catalysts can be used to perform aldol reactions, conjugate additions, Michael additions, Robinson annulations, Mannich reactions, α-aminooxylations, α-hydroxyaminations, α-aminations and alkylation reactions. Certain of such reactions are intramolecular cyclizations used to form cyclic compounds, such as 5- or 6-membered rings, having one or more chiral centers. Disclosed organocatalysts generally are much more soluble in typical solvents used for organic synthesis than are known compounds. Moreover, the reaction yield is generally quite good with disclosed compounds, as is their enantioselective and diastereoselective effectiveness.

  披露了具有如下一般公式之一的有机催化剂，尤其是脯氨酸磺酰胺有机催化剂。还披露了使用这些有机催化剂的方法的实施例。该方法包括提供一种披露的有机催化剂，并使用该有机催化剂进行反应，通常是立体选择性的反应或对映选择性反应。仅作为示例，披露的催化剂可用于进行aldol反应、共轭加成、Michael加成、Robinson环化反应、Mannich反应、α-氨基氧化、α-羟基胺化、α-胺化和烷基化反应。其中一些反应是分子内环化反应，用于形成具有一个或多个手性中心的环状化合物，例如5或6元环。披露的有机催化剂通常比已知的化合物更容易溶于用于有机合成的典型溶剂中。此外，使用披露化合物的反应收率通常相当好，它们的对映选择性和非对映选择性效果也很好。
• Reactions of polyfluoroarenes with hexamethyldisilazane and with 1,1,1-trimethyl-N,N,-bis(trimethylsilyl) stannaneamine in the presence of caesium fluoride
  作者：Alexey O. Miller、Georgii G. Furin

  DOI：10.1016/0022-1139(95)03269-6

  日期：1995.12

  Hexamethyldisilazane and 1,1,1-trimethyl-N,N-bis(trimethylsilyl) stannaneamine aminate pentafluoropyridine, octafluorotoluene, pentafluorobenzonitrile, pentafluoronitrobenzene and pentafluorobenzene sulphonyl fluoride in the presence of caesium fluoride with formation of the corresponding perfluorinated aryl amines (ArNH2), diarylamines (Ar2NH) and triarylamines (Ar3N) (where the amine functions are

  六甲基二硅氮烷和1,1,1-三甲基-N，N-双（三甲基甲硅烷基）锡胺胺五氟吡啶，八氟甲苯，五氟苄腈，五氟硝基苯和五氟苯磺酰氟，并形成相应的全氟芳基胺（ArNH 2）二芳基胺（Ar 2 NH）和三芳基胺（Ar 3 N）（其中胺官能团相对于芳烃取代基的位置为4）。
• Pentafluorophenylsulfur(IV) derivatives
  作者：William A. Sheppard、Sheila S. Foster

  DOI：10.1016/s0022-1139(00)83114-0

  日期：1972.7

  pentafluorophenylsulfur trifluoride have been prepared. Pentafluorophenylsulfur(II) derivatives are inert to oxidation to sulfur(IV) by normal procedures, but reaction of pentafluorophenyllithium with sulfur dioxide, or silver difluoride oxidative fluorination of the disulfide, provided good synthetic approaches. Chemical reactions and physical properties of these compounds are compared to those of the hydrocarbon sulfur(IV)

  一系列新的五氟苯基硫（IV）衍生物C 6 F 5 S（O）X，其中X为OLi，OH，Cl，F，OCH 3，N（CH 3）2和C 6 F 5，以及五氟苯基硫三氟化物准备好了。五氟苯基硫（II）衍生物对通过常规程序氧化成硫（IV）呈惰性，但是五氟苯基锂与二氧化硫的反应或二硫化银的二氟化银的氧化氟化提供了良好的合成方法。将这些化合物的化学反应和物理性质与烃类硫（IV）类似物以及二价和六价硫衍生物的化学反应和物理性质进行了比较，特别是在光谱性质方面。
• Unexpected distinction in reactivity of pentafluorobenzenesulfonyl halides toward organolithiums and organomagnesium halides
  作者：Vadim V. Bardin、Alexander M. Maksimov

  DOI：10.1515/znb-2017-0092

  日期：2017.9.26

  Abstract C6F5SO2Cl reacts with organolithiums and organomagnesium halides RM (R=Me, Bu, Ph; M=Li, MgX) to give mainly C6F5H and C6F5Cl. C6F5SO2Br and PhMgBr form C6F5H and (C6F5S)2. This is in contrast to known transformations of them which yield exclusively C6F5SO2Nu under the action of O- and N-nucleophiles. Alternatively, C6F5SO2F is converted to C6F5SO2R and 4-BuC6F4SO2F or 2-PhC6F4SO2Ph under

  摘要 O2Cl 与有机锂和有机卤化镁 RM (R=Me, Bu, Ph; M=Li, MgX) 反应主要生成 C6F5H 和 C6F5Cl。 O2Br 和 PhMgBr 形成 C6F5H 和 (C6F5S)2。这与它们的已知转化形成对比，后者在 O-和 N-亲核试剂的作用下仅产生 O2Nu。或者， O2F 在相同条件下转化为 O2R 和 4-BuC6F4SO2F 或 2-PhC6F4SO2Ph。当 R=Me 时，除了 O2CH3 外，还会形成少量 ( O2)2CH2 和 4- O2CH2C6F4SO2F。