Phenyl 1,2-difluoroethyl sulfide | 136370-28-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Phenyl 1,2-difluoroethyl sulfide
• 英文别名: 1,2-Difluoroethylsulfanylbenzene
• CAS: 136370-28-0
• 化学式: C₈H₈F₂S
• 分子量: 174.214
• InChiKey: NNOZDJRJPMSNSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2-Fluoroethyl)(phenyl)sulfane 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 以60%的产率得到Phenyl 1,2-difluoroethyl sulfide
  参考文献：
  名称：

  New mechanistic aspects of anodic monofluorination of halogenoalkyl and alkyl phenyl sulphides

  摘要：

  通过比较部分卤化的乙基苯硫醚（1，PhSCH2R；R = CF3, CF2H, CFH2, CF2Cl, CClH2）的阳极单氟化与其阳极甲氧基化，建立了一种通过氟磺铵离子的独特Pummerer型机制。简单的不带有电子吸引基团的烷基苯硫醚（2）在使用四氢呋喃作为溶剂时，首次能够满足产率地进行阳极单氟化反应。

  DOI：

  10.1039/c39910001027

文献信息

• Anodic functionalization of vinyl sulfides. Formal access to gem or vicinal aryl thioether dications
  作者：Didier F Andres、Eliane G Laurent、Bernard S Marquet、Hassiba Benotmane、Abdelkader Bensadat

  DOI：10.1016/0040-4020(95)00009-w

  日期：1995.2

  clearly show that the reactivity of the vinyl sulfide radical cation depends on several factors as structure of substrates and nucleophilic conditions. For example a dimerization occurred from the unsubstituted vinyl sulfide 1a (CH2=CH-SPh) whereas α,β- and/or β,β-difluoro sulfides were obtained from substituted homologues. In order to understand this reactivity the anodic behaviour of 1a and 1b (Ph-CH=CH-SPh)

  许多乙烯基硫醚的阳极氧化已在CH 3 CN-Et 3 N，3HF中进行。结果清楚地表明，乙烯基硫化物自由基阳离子的反应性取决于多种因素，如底物的结构和亲核条件。例如，未取代的乙烯基硫化物1a（CH 2＝ CH-SPh）发生了二聚，而α，β-和/或β，β-二氟硫化物是从取代的同系物获得的。为了理解这种反应性，已经特别在另外两种亲核介质（CH 3 OH / Et 3）中分析了1a和1b（Ph-CH = CH-SPh）的阳极行为。N，3HF和AcOH / AcOK）分别导致起始化合物的甲氧基化和乙酰氧基化。与电氟化结果的比较使我们能够提出一种涉及中间epi离子的机理，该机理可以解释分离产物的形成和比例。
• Electrolytic Partial Fluorination of Organic Compounds. 12. Selective Anodic Monofluorination of Fluoroalkyl and Alkyl Sulfides
  作者：Toshio Fuchigami、Akinori Konno、Kiyono Nakagawa、Moriyasu Shimojo

  DOI：10.1021/jo00099a023

  日期：1994.10

  Highly regioselective anodic monofluorination of various aryl and alkyl fluoroalkyl sulfides was successfully carried out, and fluorine was exclusively (aryl sulfides) or preferentially (alkyl sulfides) introduced at the position alpha to the fluoroalkyl group. Even simple alkyl phenyl sulfides devoid of an electron-withdrawing group could be anodically monofluorinated in satisfactory yields for the first time when etheral solvents were used as an electrolytic solution. A unique Pummerer-type mechanism uta fluorosulfonium ions was proposed for this anodic fluorination by comparison with anodic alpha-methoxylation previously studied.
• Electrolytic reactions of fluoro organic compounds. 9. Fluoride ion promoted anodic substitutions of chalcogeno compounds. 1. Regioselective anodic alkoxylation of sulfides
  作者：Toshio Fuchigami、Hidetoshi Yano、Akinori Konno

  DOI：10.1021/jo00024a002

  日期：1991.11

  Anodic alpha-alkoxylation of sulfides was remarkably promoted in the presence of fluoride ions: When Et3N.3HF was used as a supporting electrolyte, simple alkyl phenyl sulfides and sulfides bearing weak electron-withdrawing groups underwent anodic alkoxylation via fluorosulfonium ions as key intermediates in a unique Pummerer-type mechanism with reasonable or high yields for the first time.
• Fuchigami Toshio, Konno Akinori, Nakagawa Kiyono, Shimojo Moriyasu, J. Org. Chem, 59 (1994) N 20, S 5937-5941
  作者：Fuchigami Toshio, Konno Akinori, Nakagawa Kiyono, Shimojo Moriyasu

  DOI：——

  日期：——