N-(2,2,2-trichloroethylidene)trifluoromethanesulfonamide | 434340-53-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-(2,2,2-trichloroethylidene)trifluoromethanesulfonamide
• 英文别名: 1,1,1-trifluoro-N-(2,2,2-trichloroethylidene)methanesulfonamide
• CAS: 434340-53-1
• 化学式: C₃HCl₃F₃NO₂S
• 分子量: 278.467
• InChiKey: MXJUVTYJAHKCAT-UHFFFAOYSA-N

物化性质

• 沸点：
  195.6±50.0 °C(Predicted)
• 密度：
  1.81±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2,2,2-trichloroethylidene)trifluoromethanesulfonamide 在 水 作用下， 以95%的产率得到N-(2,2,2-trichloro-1-hydroxyethyl)trifluoromethanesulfonamide
  参考文献：
  名称：

  摘要：

  The reaction of N,N-dichloromethanesulfonamide with trichloroethylene gave N-(2,2,2-trichloroethylidene)trifluoromethanesulfonamide which showed high reactivity toward oxygen- and nitrogen-centered nucleophiles, as well as in C-alkylation of aromatic compounds.

  DOI：

  10.1023/a:1013899918370
• 作为产物：
  描述：

  三氯乙烯 、 N,N-dichlorotrifluoromethylsulfonamide 反应 25.0h， 以35%的产率得到N-(2,2,2-trichloroethylidene)trifluoromethanesulfonamide
  参考文献：
  名称：

  摘要：

  The reaction of N,N-dichloromethanesulfonamide with trichloroethylene gave N-(2,2,2-trichloroethylidene)trifluoromethanesulfonamide which showed high reactivity toward oxygen- and nitrogen-centered nucleophiles, as well as in C-alkylation of aromatic compounds.

  DOI：

  10.1023/a:1013899918370

文献信息

• Synthesis and reactions of 1-benzyl-3-haloalkyl-5-chloropyrazoles
  作者：E. V. Rudyakova、V. A. Savosik、I. T. Evstaf’eva、E. V. Kondrashov、G. G. Levkovskaya

  DOI：10.1134/s1070428009050108

  日期：2009.5

  pyrazoles reacted with indole and pyrrole in DMSO in the presence of alkali to give 3-(heter-1-yl)alkyl-substituted 1-benzyl-5-chloropyrazoles. 1-[(1-Benzyl-5-chloropyrazol-3-yl)methyl]indole reacted regiospecifically with chloroal trifluoromethylsulfonyl- and 4-chlorophenylsulfonylimines providing the products of C-amidotrichloroethylation into the position 3 of the indole ring. 1-[(1-Benzyl-5-c

  在碱存在下，合成的1-苄基-3-氯烷基-5-氯吡唑与吲哚和吡咯在DMSO中反应，得到3-（杂-1-基）烷基取代的1-苄基-5-氯吡唑。1-[（（1-苄基-5-氯吡唑-3-基）甲基]吲哚与氯醛三氟甲基磺酰基-和4-氯苯基磺酰亚胺类在区域上发生反应，从而将C-酰胺基三氯乙基化的产物带入吲哚环的3位。通过1-[（1-苄基-5-氯吡唑-3-基）甲基的反应获得1-[（1-苄基-5-氯吡唑-3-基）甲基]吲哚-3-基}磺酰乙酸。 ]-吲哚与碘，硫脲和氯乙酸。
• Regioselectivity in the reactions of N-(polychloroethylidene)-sulfonamides with 1H-pyrrole and 1-methyl-1H-pyrrole
  作者：I. B. Rozentsveig、B. A. Shainyan、E. V. Kondrashov、E. V. Rudyakova、G. N. Rozentsveig、K. A. Chernyshev、G. G. Levkovskaya

  DOI：10.1134/s1070428008090145

  日期：2008.9

  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.
• 10.1007/s11178-008-1010-2
  作者：Kondrashov、Rudyakova、Rozentsveig、Ushakova、Rozentsveig、Savosik、Chernyshev、Krivdin、Levkovskaya

  DOI：10.1007/s11178-008-1010-2

  日期：——
• 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.
• Structure and proton donating ability of 2- and 2,5-bis(1-trifluoromethanesulfonylamido-2,2,2-trichloroethyl)pyrroles
  作者：L. P. Oznobikhina、N. N. Chipanina、B. A. Shainyan、L. V. Sherstyannikova、V. A. Kukhareva、T. N. Aksamentova、E. V. Kondrashov、G. G. Levkovskaya

  DOI：10.1134/s107036320902025x

  日期：2009.2

  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.