N-[2,2,2-trichloro-1-(4-chlorophenylsulfonylamino)ethyl]ethanedithioamide | 1257096-42-6

• 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-(4-chlorophenylsulfonylamino)ethyl]ethanedithioamide
• 英文别名: N-[1-(4-chlorophenylsulfonylamino)-2,2,2-trichloroethyl]dithiooxamide；{[1-(4-chlorophenyl)sulfonylamino-2,2,2-trichloro]ethyl}dithiooxamide；N-[2,2,2-trichloro-1-(4-chlorophenylsulfonyl-amino)ethyl]ethanedithioamide；N'-[2,2,2-trichloro-1-[(4-chlorophenyl)sulfonylamino]ethyl]ethanedithioamide
• CAS: 1257096-42-6
• 化学式: C₁₀H₉Cl₄N₃O₂S₃
• 分子量: 441.21
• InChiKey: ZYZGPSCLRICCJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(2,2,2-三氯亚乙基)-4-氯苯磺酰胺 、 二硫代乙酰胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以77%的产率得到N-[2,2,2-trichloro-1-(4-chlorophenylsulfonylamino)ethyl]ethanedithioamide
  参考文献：
  名称：

  Functionalization of highly electrophilic N-(2,2,2-trichloroethylidene)- and N-(2,2-dichloro-2-phenylethylidene) arenesulfonamides with dithiooxamide

  摘要：

  Depending on the reactant ratio, dithiooxamide (ethanedithioamide) reacted as N-nucleophile or N,N'-binucleophile with highly electrophilic aldimines, N-(2,2,2-trichloroethylidene)- and N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides, to give the corresponding mono- or bis-adducts, N-[2-polychloro-1-(arylsulfonylamino) ethyl]ethanedithioamides or N,N'-bis[2-polychloro-1-(arylsulfonylamino)ethyl]ethanedithioamides, in good yield.

  DOI：

  10.1134/s1070428012040021

文献信息

• Intramolecular hydrogen bonds in the sulfonamide derivatives of oxamide, dithiooxamide, and biuret. FT-IR and DFT study, AIM and NBO analysis
  作者：B.A. Shainyan、N.N. Chipanina、T.N. Aksamentova、L.P. Oznobikhina、G.N. Rosentsveig、I.B. Rosentsveig

  DOI：10.1016/j.tet.2010.08.076

  日期：2010.10

  The hydrogen bonding in [(1-arylsulfonylamino-2,2,2-trichloro)ethyl]biuret 1, [(1-arylsulfonylamino-2,2,2-trichloro)ethyl]oxamide 2, and [(1-arylsulfonylamino-2,2,2-trichloro)ethyl]dithiooxamide 3, the sulfonamide derivatives of biuret 4, oxamide 5, and dithiooxamide 6, has been studied by molecular spectroscopy and DFT theoretical calculations including frequency calculations, at the B3LYP/6-311+G (d,p) level of theory. The analysis of the C=O center dot center dot center dot HN and C=S center dot center dot center dot HN intramolecular hydrogen bonds closing the five- and six-membered rings employing the atoms-in-molecules (AIM) method using the MP2(full)/6-311++G(d,p) wave functions has shown that their stability is increased in comparison to the original molecules and is much higher in the thiocarbonyl compounds. The results of the AIM and the NBO analysis of donor acceptor interactions are in good agreement with each other and with the experimental FT-IR spectroscopy data. (C) 2010 Elsevier Ltd. All rights reserved.
• Functionalization of highly electrophilic N-(2,2,2-trichloroethylidene)- and N-(2,2-dichloro-2-phenylethylidene) arenesulfonamides with dithiooxamide
  作者：G. N. Rozentsveig、A. I. Fedotova、V. Yu. Serykh、K. A. Chernyshev、I. B. Rozentsveig

  DOI：10.1134/s1070428012040021

  日期：2012.4

  Depending on the reactant ratio, dithiooxamide (ethanedithioamide) reacted as N-nucleophile or N,N'-binucleophile with highly electrophilic aldimines, N-(2,2,2-trichloroethylidene)- and N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides, to give the corresponding mono- or bis-adducts, N-[2-polychloro-1-(arylsulfonylamino) ethyl]ethanedithioamides or N,N'-bis[2-polychloro-1-(arylsulfonylamino)ethyl]ethanedithioamides, in good yield.