(3-nitrobenzyl)(trifluoromethyl)sulfane | 1444123-89-0

• 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: (3-nitrobenzyl)(trifluoromethyl)sulfane
• 英文别名: (3-Nitrobenzyl)(trifluoromethyl) sulfide；1-nitro-3-(trifluoromethylsulfanylmethyl)benzene
• CAS: 1444123-89-0
• 化学式: C₈H₆F₃NO₂S
• 分子量: 237.202
• InChiKey: XZUINNZEIYHWBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  三氟甲基硫醇（2,2-联吡啶）铜（I） 、 3-硝基溴苄 以 乙腈 为溶剂， 反应 8.0h， 以96%的产率得到(3-nitrobenzyl)(trifluoromethyl)sulfane
  参考文献：
  名称：

  Room temperature nucleophilic trifluoromethylthiolation of benzyl bromides with (bpy)Cu(SCF3)

  摘要：

  The nudeophilic trifluoromethylthiolation of benzyl bromides using (bpy)Cu(SCF3) gave the desired products of benzyl trifluoromethyl sulfides in good to excellent yields. A diverse set of important functional groups including cyano, nitro, ester, alkoxy, halide, and heterocyclic groups can be well tolerated in the protocol. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.073

文献信息

• Deoxytrifluoromethylthiolation and Selenylation of Alcohols by Using Benzothiazolium Reagents
  作者：Stefan Dix、Michael Jakob、Matthew N. Hopkinson

  DOI：10.1002/chem.201901607

  日期：2019.6.7

  Aliphatic compounds substituted with medicinally important trifluoromethylthio (SCF3) and trifluoromethylselenyl (SeCF3) groups were synthesized directly from alcohols by using the new benzothiazolium salts BT‐SCF3 and BT‐SeCF3. These bench‐stable fluorine‐containing reagents are facile to use and can be prepared in two steps from non‐fluorinated heteroaromatic starting materials. The metal‐free d

  使用新的苯并噻唑鎓盐BT-SCF 3和BT-SeCF 3从醇中直接合成被医学上重要的三氟甲硫基（SCF 3）和三氟甲基硒基（SeCF 3）取代的脂肪族化合物。这些台式稳定的含氟试剂易于使用，可以由非氟化杂芳族原料分两步制备。使用BT-SCF 3的无金属脱氧三氟甲基硫醇化过程在温和条件下进行，使用BT-SeCF 3的三氟甲基硒基化反应同样有效 据我们所知，这是首次报道这种转变的例子。
• [EN] FLUORINE-CONTAINING COMPOUNDS FOR USE AS NUCLEOPHILIC REAGENTS FOR TRANSFERRING FUNCTIONAL GROUPS ONTO HIGH VALUE ORGANIC COMPOUNDS<br/>[FR] COMPOSÉS CONTENANT DU FLUOR DESTINÉS À ÊTRE UTILISÉS EN TANT QUE RÉACTIFS NUCLÉOPHILES POUR TRANSFÉRER DES GROUPES FONCTIONNELS SUR DES COMPOSÉS ORGANIQUES À VALEUR ÉLEVÉE
  申请人：UNIV BERLIN FREIE

  公开号：WO2020141195A1

  公开（公告）日：2020-07-09

  The present invention relates to a compound of general formulae (I) and their use as reagents

  本发明涉及一种一般式(I)的化合物及其作为试剂的用途。
• An efficient and practical approach to trifluoromethylthiolation of α-haloketones/α-haloarylmethanes
  作者：Min Jiang、Fangxia Zhu、Haoyue Xiang、Xing Xu、Lianfu Deng、Chunhao Yang

  DOI：10.1039/c5ob00858a

  日期：——

  An efficient and practical approach to the trifluoromethylthiolation of α-haloketones/α-haloarylmethanes was developed, providing an unprecedentedly easy entry to various α-SCF₃-substituted ketones/arylmethanes.

  一种高效实用的方法用于三氟甲硫基化α-卤代酮/α-卤代芳基甲烷，为各种α-SCF₃取代酮/芳基甲烷提供了前所未有的简便途径。
• Enantioselective Vinylogous Mannich‐Type Reactions to Construct CF ₃ S‐Containing Stereocenters Catalysed by Chiral Quaternary Phosphonium Salts
  作者：Lijun Xu、Longhui Yu、Jun Liu、Hongyu Wang、Changwu Zheng、Gang Zhao

  DOI：10.1002/adsc.201901621

  日期：2020.4.27

  A series of benzyl trifluoromethyl sulphides bearing a nitro group were utilized as CF3S‐containing building blocks to construct chiral CF3S‐containing molecules via enantioselective vinylogous Mannich‐type reactions. In such reactions, high yields and enantioselectivities were obtained using chiral quaternary phosphonium salts derived from amino acids. Moreover, a chiral cyclic urea bearing the CF3S

  一系列带有硝基的苄基三氟甲基硫化物被用作含CF 3 S的结构单元，通过对映选择性乙烯基类Mannich型反应构建手性CF 3 S分子。在这种反应中，使用衍生自氨基酸的手性季phospho盐可获得高产率和对映选择性。此外，从产物的进一步转化获得带有CF 3 S部分的手性环状脲。
• Dehydroxytrifluoromethylthiolation(selenolation) of alcohols with C S(Se)CF3 reagent based on imidazole skeleton
  作者：Zhenyu Wang、Jiaxin Hu、Wei Liu、Chao Chen

  DOI：10.1016/j.tetlet.2023.154670

  日期：2023.9

  Direct trifluoromethylthiolation and trifluoromethylselenolation of alcohols with the new CS(Se)CF3 reagent based on imidazole skeleton has been realized. The reaction proceeds smoothly at room temperature under transition-metal-free conditions and affords the corresponding trifluoromethylthiolated and trifluoromethylselenolated products in good yields. Advantages of the method include mildness, good

  实现了基于咪唑骨架的新型C S(Se)CF 3试剂对醇的直接三氟甲硫基化和三氟甲基硒化。该反应在室温、无过渡金属的条件下顺利进行，并以良好的收率得到相应的三氟甲基硫醇化和三氟甲基硒化产物。该方法具有温和、相容性好、效率高、官能团耐受性好以及复杂醇的后期脱羟基三氟甲基硒化等优点。