(E)-1-fluoro-3-(2-tosylvinyl)benzene | 1426679-19-7

• 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: (E)-1-fluoro-3-(2-tosylvinyl)benzene
• 英文别名: 1-fluoro-3-[(E)-2-(4-methylphenyl)sulfonylethenyl]benzene
• CAS: 1426679-19-7
• 化学式: C₁₅H₁₃FO₂S
• 分子量: 276.331
• InChiKey: KEXSZLNCWHZVSY-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氟苯乙烯 、 sodium 4-methylbenzenesulfinate 在 tetrabutylammonium tetrafluoroborate 、 溶剂黄146 、 potassium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 以86%的产率得到(E)-1-fluoro-3-(2-tosylvinyl)benzene
  参考文献：
  名称：

  Electrochemical Synthesis of Vinyl Sulfones by Sulfonylation of Styrenes with a Catalytic Amount of Potassium Iodide

  摘要：

  一种苯乙烯的电化学磺化反应被开发出来，其中使用苯基亚砜钠作为磺化试剂，使用催化量的碘化钾作为氧化还原中介体，以及使用Bu4NBF4作为电解质。除了各种苯乙烯外，带有供电子基团或吸电子基团的苯基亚砜钠也能被容忍。

  DOI：

  10.1055/s-0040-1707249

文献信息

• The Synthesis of (<i>E)‐</i>Vinyl and Alkynyl Sulfones by the Formation of an Electron Donor‐Acceptor Complex Using Thiosulfonates and Sodium Iodide Under Visible Light
  作者：Kun Cao、Naiyou Zhang、Li Lin、Qing Shen、Hezhong Jiang、Jiahong Li

  DOI：10.1002/adsc.202300991

  日期：2024.1.30

  A method for the synthesis of (E)-vinyl sulfones and alkynyl sulfones through the cleavage of thiosulfonate promoted by the formation of EDA complexes under visible light irradiation at room temperature without the need for other metal catalysts is described. The mechanism study shows that sodium iodide and thiosulfonate form EDA complexes under visible light irradiation, resulting in a single-electron

  描述了一种在室温下可见光照射下通过形成EDA络合物促进硫代磺酸盐裂解合成( E )-乙烯基砜和炔基砜的方法，而不需要其他金属催化剂。机理研究表明，碘化钠和硫代磺酸盐在可见光照射下形成EDA络合物，导致单电子转移裂解生成磺酰自由基，然后与烯烃或炔烃反应，分别生成(E)-乙烯基砜或炔基砜。该方法适用于44种烯烃和炔烃底物，收率范围为38%~90%，为磺酰化化合物的制备提供了一种自由基合成途径。
• An Improved Synthesis of Vinyl- and β-Iodovinyl Sulfones by a Molecular Iodine-Mediated One-Pot Iodosulfonation-Dehydroiodination Reaction
  作者：Tassaporn Sawangphon、Praewpan Katrun、Korbua Chaisiwamongkhol、Manat Pohmakotr、Vichai Reutrakul、Thaworn Jaipetch、Darunee Soorukram、Chutima Kuhakarn

  DOI：10.1080/00397911.2012.663448

  日期：2013.6.18

  An improved one-pot method to synthesize vinyl sulfones from unsaturated systems by using molecular iodine/sodium arenesulfinate/sodium acetate as reagents was described. Vinyl sulfones derived from styrene derivatives were generally obtained in good to excellent yields except for those bearing strong electron releasing substituent. Aliphatic alkenes and activated alkenes gave the corresponding vinyl sulfone products in moderate to good yields. Arylacetylenes yielded the respective -iodovinyl sulfones in good yields while low yield was observed with aliphatic terminal alkyne. The potentials of the method entail simplicity, short reaction time, non-anhydrous reaction conditions, employing inexpensive, non-metallic reagent and integrating two reactions that are commonly accomplished separately into a single operation.