2-(p-tolyl)-5-((trifluoromethyl)thio)-1H-pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(p-tolyl)-5-((trifluoromethyl)thio)-1H-pyrrole
• 英文别名: 2-(4-tolyl)-5-[(trifluoromethyl)thio]pyrrole；2-(4-methylphenyl)-5-(trifluoromethylsulfanyl)-1H-pyrrole
• 化学式: C₁₂H₁₀F₃NS
• 分子量: 257.279
• InChiKey: BOWQIHRSOOKAGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  bis(4-methylphenyl)iodonium trifluoromethanesulfonate 在 sodium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 2-(p-tolyl)-5-((trifluoromethyl)thio)-1H-pyrrole
  参考文献：
  名称：

  Transition-Metal-Free Trifluoromethylthiolation of N-Heteroarenes

  摘要：

  AbstractA general and efficient methodology for the direct transition metal free trifluoromethylthiolation of a broad range of biologically relevant N‐heteroarenes is reported employing abundant sodium chloride as the catalyst. This method is operationally simple, exhibits high functional group tolerance, and does not require protecting groups.

  DOI：

  10.1002/chem.201500957

文献信息

• Copper-Catalyzed Regioselective Trifluoromethylthiolation of Pyrroles by Trifluoromethanesulfonyl Hypervalent Iodonium Ylide
  作者：Zhongyan Huang、Yu-Dong Yang、Etsuko Tokunaga、Norio Shibata

  DOI：10.1021/ol503616y

  日期：2015.3.6

  The copper-catalyzed trifluoromethylthiolation of pyrroles with a trifluoromethanesulfonyl hypervalent iodonium ylide under mild conditions has been achieved. A broad set of pyrroles could be transformed to the corresponding products in moderate to excellent yields. The reaction mechanism is hypothesized.

  在温和的条件下，已实现了铜的三氟甲磺酰基高价碘鎓叶立德与吡咯的铜催化三氟甲基硫醇化反应。大量的吡咯可以中等至极好的收率转化为相应的产物。假设反应机理。
• Novel Use of CF₃SO₂Cl for the Metal-Free Electrophilic Trifluoromethylthiolation
  作者：Hélène Chachignon、Mayaka Maeno、Hiroya Kondo、Norio Shibata、Dominique Cahard

  DOI：10.1021/acs.orglett.6b01026

  日期：2016.5.20

  regioselective trifluoromethylthiolation of indole derivatives was achieved under reductive conditions with trifluoromethanesulfonyl chloride as the readily available source of electrophilic SCF3 and a phosphine as the reducing agent. It is a straightforward process free from any metal and also applicable for the trifluoromethylthiolation of other azaarenes, enamines, and enoxysilanes.

  吲哚衍生物的区域选择性三氟甲基硫醇化反应是在还原条件下用三氟甲磺酰氯作为亲电SCF3的容易获得的来源和膦作为还原剂而实现的。这是一种不含任何金属的简单方法，也适用于其他氮杂芳烃，烯胺和环氧硅烷的三氟甲基硫醇化反应。
• Transition-Metal-Free Trifluoromethylthiolation of N-Heteroarenes
  作者：Roman Honeker、Johannes B. Ernst、Frank Glorius

  DOI：10.1002/chem.201500957

  日期：2015.5.26

  AbstractA general and efficient methodology for the direct transition metal free trifluoromethylthiolation of a broad range of biologically relevant N‐heteroarenes is reported employing abundant sodium chloride as the catalyst. This method is operationally simple, exhibits high functional group tolerance, and does not require protecting groups.