p-Methoxyphenyl 1,2,2,2-tetrafluoroethyl sulfide | 130612-78-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: p-Methoxyphenyl 1,2,2,2-tetrafluoroethyl sulfide
• 英文别名: 1-Methoxy-4-[(1,2,2,2-tetrafluoroethyl)sulfanyl]benzene；1-methoxy-4-(1,2,2,2-tetrafluoroethylsulfanyl)benzene
• CAS: 130612-78-1
• 化学式: C₉H₈F₄OS
• 分子量: 240.222
• InChiKey: QBNISXQTKGSIRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4-methoxyphenyl)(2,2,2-trifluoroethyl)sulfane 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 以56%的产率得到p-Methoxyphenyl 1,2,2,2-tetrafluoroethyl sulfide
  参考文献：
  名称：

  Electrolytic partial fluorination of organic compounds. 1. Regioselective anodic monofluorination of organosulfur compounds

  摘要：

  DOI：

  10.1021/jo00312a006

文献信息

• Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers
  作者：Conor E. Brigham、Christian A. Malapit、Naish Lalloo、Melanie S. Sanford

  DOI：10.1021/acscatal.0c02950

  日期：2020.8.7

  This report describes the development of a nickel-catalyzed decarbonylative reaction for the synthesis of fluoroalkyl thioethers (RFSR) from the corresponding thioesters. Readily available, inexpensive, and stable fluoroalkyl carboxylic acids (RFCO2H) serve as the fluoroalkyl (RF) source in this transformation. Stoichiometric organometallic studies reveal that RF–S bond-forming reductive elimination

  本报告描述了镍催化脱羰反应的发展，用于从相应的硫酯合成氟烷基硫醚 (R F SR)。容易获得、便宜且稳定的氟代烷基羧酸 (R F CO 2 H) 作为该转化中的氟代烷基 (R F ) 源。化学计量有机金属研究表明，形成R F -S 键的还原消除是催化循环中的一个具有挑战性的步骤。这导致二苯基膦二茂铁被鉴定为该转化的最佳配体。最终，该方法应用于构建多种氟代烷基硫醚 (R F SR)，其中 R = 芳基和烷基。
• Electrolytic partial fluorination of organic compounds. 1. Regioselective anodic monofluorination of organosulfur compounds
  作者：Toshio Fuchigami、Moriyasu Shimojo、Akinori Konno、Kiyono Nakagawa

  DOI：10.1021/jo00312a006

  日期：1990.12
• FUCHIGAMI, TOSHIO;SHIMOJO, MORIYASU;KONNO, AKINORI;NAKAGAWA, KIYONO, J. ORG. CHEM., 55,(1990) N5, C. 6074-6075
  作者：FUCHIGAMI, TOSHIO、SHIMOJO, MORIYASU、KONNO, AKINORI、NAKAGAWA, KIYONO

  DOI：——

  日期：——
• 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：——
• 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.