bis(4-trifluoromethylbenzyl) sulfide | 1190622-44-6

• 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: bis(4-trifluoromethylbenzyl) sulfide
• 英文别名: Bis[4-(trifluoromethyl)benzyl] sulfide；1-(trifluoromethyl)-4-[[4-(trifluoromethyl)phenyl]methylsulfanylmethyl]benzene
• CAS: 1190622-44-6
• 化学式: C₁₆H₁₂F₆S
• 分子量: 350.328
• InChiKey: XZHQIVIWWYSJMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• 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：
  7

反应信息

• 作为反应物：
  描述：

  bis(4-trifluoromethylbenzyl) sulfide 在 双氧水 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 以8.79 g的产率得到bis<4-(3-trifluoromethyl)benzyl> sulfone
  参考文献：
  名称：

  Synthesis of New Lipophilic Sulfones and Their Use in Cyclization Reactions

  摘要：

  Analytically pure novel dibenzylsulfanes 2a,b were synthesized by established reactions. Their oxidation by hydrogen peroxide resulted in the formation of the corresponding sulfones 3a,b, which were isolated in high yields. Analogously, the new bis-sulfone 7 was prepared starting from bis-bromo derivative 4 via bis-sulfane 6. The sulfones obtained reacted readily with bis-imidoylchlorides 8, yielding highly substituted dihydrothiophene-S,S-dioxides of type 9 and 10. Due to their vicinal amino-imino substructures, these cyclic sulfones proved to be excellent chelating ligands, exemplified by the preparation of the palladium complex 11.

  DOI：

  10.1080/10426500902855208
• 作为产物：
  描述：

  4-trifluoromethylbenzyl tosylate 在 sodium sulfide trihydrate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以81%的产率得到bis(4-trifluoromethylbenzyl) sulfide
  参考文献：
  名称：

  Synthesis of New Lipophilic Sulfones and Their Use in Cyclization Reactions

  摘要：

  Analytically pure novel dibenzylsulfanes 2a,b were synthesized by established reactions. Their oxidation by hydrogen peroxide resulted in the formation of the corresponding sulfones 3a,b, which were isolated in high yields. Analogously, the new bis-sulfone 7 was prepared starting from bis-bromo derivative 4 via bis-sulfane 6. The sulfones obtained reacted readily with bis-imidoylchlorides 8, yielding highly substituted dihydrothiophene-S,S-dioxides of type 9 and 10. Due to their vicinal amino-imino substructures, these cyclic sulfones proved to be excellent chelating ligands, exemplified by the preparation of the palladium complex 11.

  DOI：

  10.1080/10426500902855208

文献信息

• Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides
  作者：Ting Liu、Renhua Qiu、Longzhi Zhu、Shuang-Feng Yin、Chak-Tong Au、Nobuaki Kambe

  DOI：10.1002/asia.201801679

  日期：2018.12.18

  A site‐selective metal‐free dealkylative approach to synthesize aryl alkyl and symmetrical dialkyl sulfides has been developed. This procedure is convenient and has wide functional group tolerance giving rise to sulfides carrying various alkyl chains from simple alkyl sulfides and alkyl halides in good to excellent yields. This transalkylation proceeds by an ionic mechanism via sulfonium intermediates

  已经开发出了一种位点选择的无金属脱烷基方法来合成芳基烷基和对称的二烷基硫化物。该方法是方便的并且具有宽的官能团耐受性，从而以良好的至优异的产率产生了从简单的烷基硫化物和烷基卤化物携带带有各种烷基链的硫化物。这种烷基转移反应是通过ionic中间体通过离子机理进行的，有人提出，二甲基乙酰胺（DMAC）可以部分参与促进反应。
• Indium-catalyzed Direct Conversion of Dibenzyl Ethers to Dibenzyl Sulfides Using Elemental Sulfur and a Hydrosilane and Its Application to the Preparation of Benzyl Selenides
  作者：Norio Sakai、Koji Takada、Masahiro Katayama、Yohei Ogiwara

  DOI：10.1246/cl.180242

  日期：2018.6.5

  compound, a hydrosilane and an easily handled form of elemental sulfur (S8) that effectively and directly catalyzes the sulfidation of dibenzyl ethers to produce dibenzyl sulfides. This system could also be applied to selenium in a straightforward conversion to dibenzyl selenides.

  本文描述了由铟(III)化合物、氢硅烷和易于处理的元素硫(S8)形式组成的催化体系，其有效且直接地催化二苄基醚硫化以产生二苄基硫化物。该系统也可以直接转化为二苄基硒化物而应用于硒。
• [EN] SULFUR EXTRUSION FROM DISULFIDES BY CARBENES<br/>[FR] EXTRUSION DE SOUFRE À PARTIR DE DISULFURES PAR DES CARBÈNES
  申请人：UNIV HEIDELBERG

  公开号：WO2021214243A1

  公开（公告）日：2021-10-28

  The present invention relates to a method for preparing a compound T having a thioether group from a compound D having a disulfide group in the presence of a carbene.

  本发明涉及一种在卡宾的存在下，从具有二硫键的化合物D制备具有硫醚基团的化合物T的方法。
• N‐Heterocyclic Carbene Mediated Sulfur Extrusion of Disulfides
  作者：Alexander P. Galow、Frank Rominger、Michael Mastalerz

  DOI：10.1002/ejoc.202201383

  日期：2023.2.13

  N-heterocyclic carbenes can be used to substitute the highly carcinogenic aminophosphines to extrude sulfur from disulfides from thioethers (here R=aryl). Furthermore, pharmaceutically more interesting compounds such as cystine can be transformed to lanthionine.

  N-杂环卡宾可用于替代高度致癌的氨基膦，以从硫醚（此处 R = 芳基）的二硫化物中挤出硫。此外，药学上更有趣的化合物如胱氨酸可以转化为羊毛硫氨酸。
• SULFUR EXTRUSION FROM DISULFIDES BY CARBENES
  申请人：Universität Heidelberg

  公开号：EP3901135A1

  公开（公告）日：2021-10-27

  The present invention relates to a method for preparing a compound T having a thioether group from a compound D having a disulfide group in the presence of a carbene.

  本发明涉及一种在碳烯存在下从具有二硫化物基团的化合物 D 中制备具有硫醚基团的化合物 T 的方法。