2-(2,2-difluoroethenyl)furan | 1608-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(2,2-difluoroethenyl)furan
• 英文别名: 2-(2,2-Difluoroethenyl)furan
• CAS: 1608-22-6
• 化学式: C₆H₄F₂O
• 分子量: 130.094
• InChiKey: RKKYGJZTMWUWIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 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：
  13.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,2-difluoroethenyl)furan 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 9-苯基吖啶 、 维生素 C 作用下， 以 环己烷 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  从二氟苯乙烯生成氟自由基的新型光氧化还原活性基团

  摘要：

  建议使用4-四氟吡啶基硫基作为新的光氧化还原活性部分。该基团可通过硫烯点击反应一步一步直接安装在二氟苯乙烯上。它在可见光催化下用9-苯基ac啶进行反应，提供各种二氟化硫醚作为自由基前体。贫电子的嗪环可实现C–S键的单电子还原以及氟烷基的形成。中间体二氟化硫与甲硅烷基烯醇醚，烯烃，硝酮和烯基三氟硼酸酯发生一系列光氧化还原反应。

  DOI：

  10.1039/c9sc04643g
• 作为产物：
  描述：

  糠醛 、 氟磺酰基二氟乙酸甲酯 在 三苯基膦 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以54%的产率得到2-(2,2-difluoroethenyl)furan
  参考文献：
  名称：

  The use of methyl 2,2-difluoro-2-(fluorosulfonyl)acetate as the difluorocarbene source to generate an in situ source of difluoromethylene triphenylphosphonium ylide

  摘要：

  Under moderate conditions in the presence of a demethylating reagent, such as iodide, methyl 2,2,-difluoro-2-(fluorosulfonyl)acetate (MDFA) releases difluorocarbene, which in the presence of triphenylphosphine forms difluoromethylene triphenylphosphonium ylide. When the process is carried out also in the presence of aldehydes or activated ketones, the ensuing in situ Wittig-type reaction of the ylide with the carbonyl reactants produces 1,1-difluoroalkenes in good yield. Density Functional Theory calculations were used to provide new estimates of the energies and structures of singlet and triplet states of CH2:, CHF:, and CF2: carbenes, as well as those of their respective triphenylphosphonium ylides. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.02.026

文献信息

• The use of methyl 2,2-difluoro-2-(fluorosulfonyl)acetate as the difluorocarbene source to generate an in situ source of difluoromethylene triphenylphosphonium ylide
  作者：Charles S. Thomoson、Henry Martinez、William R. Dolbier

  DOI：10.1016/j.jfluchem.2013.02.026

  日期：2013.6

  Under moderate conditions in the presence of a demethylating reagent, such as iodide, methyl 2,2,-difluoro-2-(fluorosulfonyl)acetate (MDFA) releases difluorocarbene, which in the presence of triphenylphosphine forms difluoromethylene triphenylphosphonium ylide. When the process is carried out also in the presence of aldehydes or activated ketones, the ensuing in situ Wittig-type reaction of the ylide with the carbonyl reactants produces 1,1-difluoroalkenes in good yield. Density Functional Theory calculations were used to provide new estimates of the energies and structures of singlet and triplet states of CH2:, CHF:, and CF2: carbenes, as well as those of their respective triphenylphosphonium ylides. (C) 2013 Elsevier B.V. All rights reserved.
• A novel photoredox-active group for the generation of fluorinated radicals from difluorostyrenes
  作者：Mikhail O. Zubkov、Mikhail D. Kosobokov、Vitalij V. Levin、Vladimir A. Kokorekin、Alexander A. Korlyukov、Jinbo Hu、Alexander D. Dilman

  DOI：10.1039/c9sc04643g

  日期：——

  by the thiolene click reaction. It proceeds upon visible light catalysis with 9-phenylacridine providing various difluorinated sulfides as radical precursors. Single electron reduction of the C–S bond with the formation of fluoroalkyl radicals is enabled by the electron-poor azine ring. The intermediate difluorinated sulfides were involved in a series of photoredox reactions with silyl enol ethers

  建议使用4-四氟吡啶基硫基作为新的光氧化还原活性部分。该基团可通过硫烯点击反应一步一步直接安装在二氟苯乙烯上。它在可见光催化下用9-苯基ac啶进行反应，提供各种二氟化硫醚作为自由基前体。贫电子的嗪环可实现C–S键的单电子还原以及氟烷基的形成。中间体二氟化硫与甲硅烷基烯醇醚，烯烃，硝酮和烯基三氟硼酸酯发生一系列光氧化还原反应。