α-Fluoro-α-(phenylthio)acetophenone | 134988-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-Fluoro-α-(phenylthio)acetophenone
• 英文别名: 2-fluoro-1-phenyl-2-(phenylthio)ethan-1-one；2-fluoro-1-phenyl-2-(phenylthio)ethanone；Ethanone, 2-fluoro-1-phenyl-2-(phenylthio)-；2-fluoro-1-phenyl-2-phenylsulfanylethanone
• CAS: 134988-41-3
• 化学式: C₁₄H₁₁FOS
• 分子量: 246.305
• InChiKey: RCUFAUZWAROMQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-Fluoro-α-(phenylthio)acetophenone 在 triethylamine tris(hydrogen fluoride) 作用下， 以91%的产率得到2,2-difluoro-1-phenyl-2-(phenylsulfanyl)ethanone
  参考文献：
  名称：

  Et 3 N.3HF存在下硫化物的氧化氟化

  摘要：

  描述了使用Et 3 N.3HF作为氟化剂通过硫化物电化学氧化合成氟化合物的方法。化学氧化（DBH）效率较低。

  DOI：

  10.1016/0040-4039(90)80208-4
• 作为产物：
  描述：

  苯甲酰甲基苯基硫醚 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 以87%的产率得到α-Fluoro-α-(phenylthio)acetophenone
  参考文献：
  名称：

  Et 3 N.3HF存在下硫化物的氧化氟化

  摘要：

  描述了使用Et 3 N.3HF作为氟化剂通过硫化物电化学氧化合成氟化合物的方法。化学氧化（DBH）效率较低。

  DOI：

  10.1016/0040-4039(90)80208-4

文献信息

• Efficient Monofluoroalkylation of Thiophenols or Phenols with α-Bromo-α-Fluoroketones under Mild Conditions
  作者：Jingjing Wu、Fanhong Wu、Zhi Li、Mougui Fang、Yunli Liu、Yecheng Liu

  DOI：10.1055/a-1395-4788

  日期：2021.7

  nucleophilic substitution reaction between α-bromo-α-fluoroketones and thiophenols or phenols is reported for the synthesis of α-fluoro-β-ketosulfides or α-fluoro-β-ketone ethers in yields ranging from 78–93%. This method exhibits good functional group tolerance and a broad scope of nucleophilic substrates, including natural phenolic compounds.

  据报道，α-溴-α-氟代酮与硫酚或苯酚之间的有效亲核取代反应可合成α-氟代-β-酮硫醚或α-氟代-β-酮醚，产率为78-93％。该方法表现出良好的官能团耐受性和广泛的亲核底物，包括天然酚类化合物。
• A Route to α-Fluoroalkyl Sulfides from α-Fluorodiaroylmethanes
  作者：Ya-mei Lin、Wen-bin Yi、Wan-zhao Shen、Guo-ping Lu

  DOI：10.1021/acs.orglett.5b03654

  日期：2016.2.5

  alpha,alpha-Difluorodiaroylmethane can be used as a nucleophilic difluoromethylation reagent for generating alpha-thioaryl-alpha,alpha-difluoroacetophenones ((ArCOCF2SAr)-C-1) and difluoromethylthiolated arenes (ArSCF2H) under transition-metal-free conditions. The reaction selectivity is mainly dependent on temperature. The method has also been extended to the synthesis of alpha-thioaryl-alpha-monofluoroacetophenones using alpha-monofluorodibenzoylmethane. Moreover, the benzoyl cation derived from alpha,alpha-difluorodibenzoylmethane can react with nucleophiles to afford the desired products in a one-pot process.
• Electrolytic Partial Fluorination of Organic Compounds. 17. Regiospecific Anodic Fluorination of Sulfides Bearing Electron-Withdrawing Substituents at the Position .alpha. to the Sulfur Atom
  作者：Toshio Fuchigami、Moriyasu Shimojo、Akinori Konno

  DOI：10.1021/jo00116a037

  日期：1995.6

  Regiospecific monofluorination of various sulfides bearing electron-withdrawing substituents, cyano, ester, acyl, amino, and phosphonate groups,at their alpha-positions was successfully carried out by the anodic oxidation of the sulfides in Et(3)N . 3HF/MeCN using an undivided cell. Fluorine was introduced at the position alpha to the sulfur atom selectively. Fluorination of alpha-(phenylthio)-substituted cyclic carbonyl compounds was also successful. Furthermore, anodic alpha,alpha-difluorination of ethyl alpha-(phenylthio)acetate was also successfully carried out although a large amount of electricity was required.
• Brigaud, Thierry; Laurent, Andre; Laurent, Eliane, Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 59, # 1-4, p. 153 - 156
  作者：Brigaud, Thierry、Laurent, Andre、Laurent, Eliane

  DOI：——

  日期：——
• BRIGAUD, TH.;LAURENT, SL., TETRAHEDRON LETT., 31,(1990) N6, C. 2287-2290
  作者：BRIGAUD, TH.、LAURENT, SL.

  DOI：——

  日期：——