N-[2,2,2-trichloro-1-(1H-pyrrol-2-yl)ethyl]benzenesulfonamide | 1107692-81-8

• 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: N-[2,2,2-trichloro-1-(1H-pyrrol-2-yl)ethyl]benzenesulfonamide
• 英文别名: N-[2,2,2-trichloro-1-(1h-pyrrol-2-yl)ethyl]-benzenesulfonamide
• CAS: 1107692-81-8
• 化学式: C₁₂H₁₁Cl₃N₂O₂S
• 分子量: 353.657
• InChiKey: UJVHVNBVCYFTOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡咯 、 N-(2,2,2-trichloroethylidene)benzenesulfonamide 以 四氯化碳 为溶剂， 反应 17.5h， 以74%的产率得到N-[2,2,2-trichloro-1-(1H-pyrrol-2-yl)ethyl]benzenesulfonamide
  参考文献：
  名称：

  Regioselectivity in the reactions of N-(polychloroethylidene)-sulfonamides with 1H-pyrrole and 1-methyl-1H-pyrrole

  摘要：

  N-(2,2,2-Trichloroethylidene)arenesulfonamides react with 1H-pyrrole and 1-methyl-1H-pyrrole to give the corresponding N-[2,2,2-trichloro-1-(1H-pyrrol-2-yl)ethyl]arenesulfonamides. The reaction of N-(2,2,2-trichloroethylidene)trifluoromethanesulfonamide with pyrrole leads to a mixture of 2-mono-and 2,5-disubstituted pyrroles, whereas in the reaction with 1-methyl-1H-pyrrole only the 2-substituted compound is formed. N-(2,2-Dichloro-2-phenylethylidene)-4-methylbenzenesulfonamide reacts with 1H-pyrrole to form N-[2,2-dichloro-2-phenyl-1-(1H-pyrrol-2-yl)ethyl]-4-methylbenzenesulfonamide, and its reaction with 1-methyl-1H-pyrrole gives a mixture of 2-and 3-monosubstituted derivatives. The results of quantum-chemical calculations of the initial reactants and products indicate that the process is orbital-controlled. A good agreement is observed between the experimental data and theoretical conclusions concerning the dependence of the reaction regioselectivity on the nature of substituents in the electrophile molecule.

  DOI：

  10.1134/s1070428008090145

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.