2-phenyl-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-phenyl-5-((trifluoromethyl)thio)-1H-pyrrole
• 英文别名: 2-phenyl-5-[(trifluoromethyl)thio]pyrrole；2-phenyl-5-(trifluoromethylsulfanyl)-1H-pyrrole
• 化学式: C₁₁H₈F₃NS
• 分子量: 243.252
• InChiKey: MWFNOLKMAZVPRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  二苯基碘三氟甲烷磺酸盐 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-phenyl-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

• Direct Trifluoromethylthiolation and Perfluoroalkylthiolation of C(sp ² )H Bonds with CF ₃ SO ₂ Na and R _f SO ₂ Na
  作者：Lvqi Jiang、Jinlong Qian、Wenbin Yi、Guoping Lu、Chun Cai、Wei Zhang

  DOI：10.1002/anie.201508495

  日期：2015.12

  A new method for CF3SO2Na‐based direct trifluoromethylthiolation of C(sp2)H bonds has been developed. CF3SSCF3 is generated in situ from cheap and easy‐to‐handle CF3SO2Na, and in the presence of CuCl can be used for electrophilic trifluoromethylthiolation of indoles, pyrroles, and enamines. The method has been extended to perfluoroalkylthiolation reactions using RfSO2Na.

  已开发出一种基于CF 3 SO 2 Na的C（sp 2）H键直接三氟甲基硫醇化的新方法。CF 3 SSCF 3是由便宜且易于处理的CF 3 SO 2 Na原位生成的，在存在CuCl的情况下，可用于吲哚，吡咯和烯胺的亲电三氟甲基硫醇化反应。该方法已扩展到使用R f SO 2 Na的全氟烷基硫醇化反应。
• 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。
• Direct Phosphorus-Induced Fluoroalkylthiolation with Fluoroalkylsulfonyl Chlorides
  作者：Lvqi Jiang、Wenbin Yi、Qiran Liu

  DOI：10.1002/adsc.201600651

  日期：2016.12.7

  A simple and practical method of fluoroalkylthiolation using fluoroalkylsulfonyl chlorides (RfSO2Cl, Rf=CF3, C4F9, C8F17, CF2H and CH2CF3) has been developed. These easy‐to‐handle reagents are powerful and can be used for electrophilic fluoroalkylthiolation of electron‐rich arenes and thiols using diethyl phosphite as reducing agent.

  已经开发了使用氟代烷基磺酰氯（R f SO 2 Cl，R f＝ CF 3，C 4 F 9，C 8 F 17，CF 2 H和CH 2 CF 3）的氟烷基硫醇化的简单实用方法。这些易于处理的试剂功能强大，可使用亚磷酸二乙酯作为还原剂，用于富电子芳烃和硫醇的亲电氟烷基硫醇化反应。
• 2‐Diazo‐1‐phenyl‐2‐((trifluoromethyl)sulfonyl)ethan‐1‐one: Another Utility for Electrophilic Trifluoromethylthiolation Reactions
  作者：Zhongyan Huang、Kenta Okuyama、Chen Wang、Etsuko Tokunaga、Xiaorui Li、Norio Shibata

  DOI：10.1002/open.201500225

  日期：2016.6

  2‐Diazo‐1‐phenyl‐2‐((trifluoromethyl)sulfonyl)ethan‐1‐one (diazo‐triflone) (2) is not only a building block but also a reagent. In this study, diazo‐triflone, which was originally used for the synthesis of β‐lactam triflones as a trifluoromethanesulfonyl (SO2CF3) building block under catalyst‐free thermal conditions, is redisclosed as an effective electrophilic trifluoromethylthiolation reagent under copper catalysis

  2-重氮-1-苯基-2-（（三氟甲基）磺酰基）乙-1-酮（重氮三酮）（2）不仅是构件，而且还是试剂。在这项研究中，重氮重氮酮原本是在无催化剂的热条件下以三氟甲磺酰基（SO 2 CF 3）结构单元的形式用于合成β-内酰胺三氟酮的，后来在铜催化下重新公开为有效的亲电子三氟甲基硫醇化试剂。将大量的烯胺，吲哚，β-酮酸酯，吡咯和苯胺很好地转化为相应的三氟甲硫基（SCF 3）在重铜催化下，通过亲电子型反应，重氮-三氢萘酮以高至高收率的化合物。重氮-三唑酮也可以以可接受的产率实现芳基碘的偶合型三氟甲基硫醇化反应。