3-(1-trifluoromethanesulfonylamido-2,2,2-trichloroethyl)-1-methylpyrrole | 1207680-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(1-trifluoromethanesulfonylamido-2,2,2-trichloroethyl)-1-methylpyrrole
• 英文别名: N-[2,2,2-trichloro-1-(1-methyl-1H-pyrrol-3-yl)-ethyl]trifluoromethanesulfonamide；1,1,1-trifluoro-N-[2,2,2-trichloro-1-(1-methylpyrrol-3-yl)ethyl]methanesulfonamide
• CAS: 1207680-68-9
• 化学式: C₈H₈Cl₃F₃N₂O₂S
• 分子量: 359.584
• InChiKey: HQNBKFMQYNWNPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-甲基吡咯 、 N-(2,2,2-trichloroethylidene)trifluoromethanesulfonamide 以 四氯化碳 、 三氯乙烯 为溶剂， 反应 6.0h， 以71%的产率得到2-(1-trifluoromethanesulfonylamido-2,2,2-trichloroethyl)-1-methylpyrrole
  参考文献：
  名称：

  Structure and proton donating ability of 2- and 2,5-bis(1-trifluoromethanesulfonylamido-2,2,2-trichloroethyl)pyrroles

  摘要：

  2-(1-Trifluoromethanesulfonylamido-2,2,2-trichloroethyl)pyrrole and 2,5-bis(1-trifluoromethanesulfonylamido-2,2,2-trichloroethyl)pyrrole according to quantum chemical calculations (B3LYP/6-311G**) exist in the isomeric forms whose structure determines the formation of intramolecular hydrogen bonds NHa <-Cl, NHa <-O=S and CHa <-O=S of different strength. Potentiometric and spectroscopic acidity of these compounds is determined. From the data of IR spectroscopy their proton donating ability upon interaction with Lewis bases is shown depending on the presence of intramolecular hydrogen bonds, mutual effects of intermolecular hydrogen bonds formed by the sulfonamide and pyrrole NH groups with the base, and electronic effects of the substituents.

  DOI：

  10.1134/s107036320902025x

文献信息

• C-amidoalkylation of pyrroles with N-trifluoromethylsulfonyl and N-arylsulfonyl polychloroaldehyde imines
  作者：E. V. Kondrashov、E. V. Rudyakova、G. N. Rozentsveig、I. B. Rozentsveig、K. A. Chernyshev、L. B. Krivdin、G. G. Levkovskaya

  DOI：10.1134/s1070428009090097

  日期：2009.9

  N-(Trifluoromethylsulfonyl) and N-arylsulfonyl polychloroacetaldehyde imines reacted with pyrrole, 1-alkyl-, 1-benzyl-, and 1-(4-nitrophenyl)-substituted pyrroles, and bis-pyrroles to give the corresponding 2-[1-(sulfonylamino)polychloroethyl]-1H-pyrroles or mixtures of 2- and 3-[1-(sulfonylamino) polychloroethyl]-1H-pyrroles, depending on the nature of the Schiff base and substituent on the pyrrole nitrogen atom and reaction conditions. The first synthesis of 2,5-disubstituted NH-pyrrole by reaction of pyrrole with Schiff bases was described.