10-((trifluoromethyl)thio)benzo[h]quinoline | 1584705-56-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 10-((trifluoromethyl)thio)benzo[h]quinoline
• 英文别名: 10-(Trifluoromethylsulfanyl)benzo[h]quinoline；10-(trifluoromethylsulfanyl)benzo[h]quinoline
• CAS: 1584705-56-5
• 化学式: C₁₄H₈F₃NS
• 分子量: 279.285
• InChiKey: HHTXKPUKQBVFGT-UHFFFAOYSA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  338.7±42.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  10-bromobenzo[h]quinoline 、 tetramethylammonium trifluoromethanethiolate 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 乙腈 为溶剂， 以90%的产率得到10-((trifluoromethyl)thio)benzo[h]quinoline
  参考文献：
  名称：

  Copper-Catalyzed Trifluoromethylthiolation of Aryl Halides with Diverse Directing Groups

  摘要：

  The expansion of cross-coupling components in Cu-catalyzed C-X bond forming reactions have received much attention recently. A novel Cu-catalyzed trifluoromethylthiolation of aryl bromides and iodides with the assistance of versatile directing groups such as pyridyl, methyl ester, amide, imine and oxime was reported. CuBr was used as the catalyst, and 1,10-phenanthroline as the ligand. By changing the solvent from acetonitrile to DMF, the coupling process could even take place at room temperature.

  DOI：

  10.1021/ol501742a

文献信息

• Palladium-Catalyzed Trifluoromethylthiolation of Chelation-Assisted C-H Bonds
  作者：Arunachalam Kesavan、Manthena Chaitanya、Pazhamalai Anbarasan

  DOI：10.1002/ejoc.201800451

  日期：2018.7.6

  Palladium‐catalyzed trifluoromethylthiolation of chelation‐assisted C–H bonds has been accomplished by employing a readily accessible electrophilic trifluoromethylthiolating reagent.

  螯合辅助CH键的钯催化三氟甲基硫醇化反应是通过使用易于获得的亲电子三氟甲基硫醇化试剂完成的。
• Palladium-Catalyzed Trifluoromethylthiolation of Aryl C–H Bonds
  作者：Chunfa Xu、Qilong Shen

  DOI：10.1021/ol5006533

  日期：2014.4.4

  A method for monotrifluoromethylthiolation of arenes via palladium-catalyzed directed C–H bond activation was described. The reaction was compatible with a variety of functional groups. Initial mechanistic studies disclosed that the turnover limiting step of the catalytic cycle did not involve C–H activation.

  描述了一种通过钯催化的直接CH键键合活化芳烃的单三氟甲基硫醇化方法。该反应与多种官能团相容。最初的机理研究表明，催化循环的周转限制步骤不涉及C–H活化。
• Selective trifluoromethylthiolation of heteroaromatic sp2 C–H bonds with the 2nd generation of trifluoromethanesulfenamide reagent
  作者：Sébastien Alazet、Luc Zimmer、Thierry Billard

  DOI：10.1016/j.jfluchem.2014.09.009

  日期：2015.3

  By applying a well-established protocol of selective deprotonation of heteroarenes, the selective trifluoromethylthiolation of various heteroaromatic compounds has been performed, by using the 2nd generation of trifluoromethanesulfenamide reagent. With such strategy, functionalized heteroarenes could be synthesized as potential trifluoromethylthiolated building-blocks. (C) 2014 Elsevier B.V. All rights reserved.