(3-bromobenzyl)(trifluoromethyl)sulfane

• 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-bromobenzyl)(trifluoromethyl)sulfane
• 英文别名: 3-bromobenzyl trifluoromethyl sulfane；3-bromo-trifluoromethylthiomethylbenzene；1-Bromo-3-(trifluoromethylsulfanylmethyl)benzene
• 化学式: C₈H₆BrF₃S
• 分子量: 271.101
• InChiKey: REWUVXIQERNPFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  13
• 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：
  25.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-bromobenzyl)(trifluoromethyl)sulfane 、 丙烯酸乙酯 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 copper diacetate 作用下， 反应 12.0h， 以82%的产率得到ethyl 4-bromo-2-((trifluoromethylthio)methyl)cinnamate
  参考文献：
  名称：

  Ir(III)-Catalyzed Mono-Olefination of Aryl C–H Bonds Using −SCF₃ as a Weak Directing Group

  摘要：

  The trifluoromethylthionyl group (-SCF3) is an efficient weak directing group for Ir(III)-catalyzed aryl C-H olefination. Various trifluoromethylthioethers provide high levels of mono-olefination products in good to excellent yields under mild conditions with a 2,2'-bipyridine ligand or AgBF4 as an additive. Mechanistic studies indicate the C-H cleavage is the rate-determining step. The directing group ability of the -SCF3 group is benchmarked against several other weak directing groups by competition experiments under Ir(III)-catalyzed conditions.

  DOI：

  10.1021/acs.orglett.9b03125
• 作为产物：
  描述：

  3-溴苄溴 、 (三氟甲硫基)银(I) 在 四丁基碘化铵 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以95%的产率得到(3-bromobenzyl)(trifluoromethyl)sulfane
  参考文献：
  名称：

  Ir(III)-Catalyzed Mono-Olefination of Aryl C–H Bonds Using −SCF₃ as a Weak Directing Group

  摘要：

  The trifluoromethylthionyl group (-SCF3) is an efficient weak directing group for Ir(III)-catalyzed aryl C-H olefination. Various trifluoromethylthioethers provide high levels of mono-olefination products in good to excellent yields under mild conditions with a 2,2'-bipyridine ligand or AgBF4 as an additive. Mechanistic studies indicate the C-H cleavage is the rate-determining step. The directing group ability of the -SCF3 group is benchmarked against several other weak directing groups by competition experiments under Ir(III)-catalyzed conditions.

  DOI：

  10.1021/acs.orglett.9b03125

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。
• TRIFLUORO METHYLTHIOMETHYL BENZENE DERIVATIVES AND PROCESS FOR PRODUCING THE SAME
  申请人：IHARA CHEMICAL INDUSTRY CO., LTD.

  公开号：EP1000933B1

  公开（公告）日：2006-08-02
• US6225505B1
  申请人：——

  公开号：US6225505B1

  公开（公告）日：2001-05-01
• Ir(III)-Catalyzed Mono-Olefination of Aryl C–H Bonds Using −SCF₃ as a Weak Directing Group
  作者：Rui-Peng Bao、Xian Chen、Chen Li、Dong-Hui Wang

  DOI：10.1021/acs.orglett.9b03125

  日期：2019.10.4

  The trifluoromethylthionyl group (-SCF3) is an efficient weak directing group for Ir(III)-catalyzed aryl C-H olefination. Various trifluoromethylthioethers provide high levels of mono-olefination products in good to excellent yields under mild conditions with a 2,2'-bipyridine ligand or AgBF4 as an additive. Mechanistic studies indicate the C-H cleavage is the rate-determining step. The directing group ability of the -SCF3 group is benchmarked against several other weak directing groups by competition experiments under Ir(III)-catalyzed conditions.