1,1bis(benzenesulfonylamino)-2,2-dichloro-2-phenylethane | 147116-70-9

• 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: 1,1bis(benzenesulfonylamino)-2,2-dichloro-2-phenylethane
• 英文别名: N,N'-(2,2-Dichloro-2-phenylethane-1,1-diyl)dibenzenesulfonamide；N-[1-(benzenesulfonamido)-2,2-dichloro-2-phenylethyl]benzenesulfonamide
• CAS: 147116-70-9
• 化学式: C₂₀H₁₈Cl₂N₂O₄S₂
• 分子量: 485.412
• InChiKey: MRFHCKTWSYFALK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯甲醚 、 1,1bis(benzenesulfonylamino)-2,2-dichloro-2-phenylethane 在 硫酸 作用下， 反应 12.0h， 以71%的产率得到N-<1-(4-Methoxyphenyl)-2-phenyl-2,2-dichloroethyl>benzenesulfonamide
  参考文献：
  名称：

  摘要：

  N-[1-4-Methoxyphenyl-2-phenyl-2,2-dichloroethyl]arenesulfonamides are formed in reaction of N-(2-phenyl,-2.2-dichloroethylidene)-4-chlorobenzenesulfonamide and N-(2-phenyl-2,2-dichloroethylidene)-4-methylbenzenesulfonamide with anisole catalyzed by boron trifluoride etherate, and in reaction of anisole with 1,1-di(arenesulfonamido)-2-phenyl-2,2,-dichloroethanes in the presence of concentrated sulfuric acid.

  DOI：

  10.1023/a:1012457430488
• 作为产物：
  描述：

  二氯胺B 、 苯乙炔 反应 1.0h， 以15%的产率得到N-(2-phenyl-2,2-dichloroethylidene)benzenesulfonamide
  参考文献：
  名称：

  Drozdova, T. I.; Levkovskaya, G. G.; Mirskova, A. N., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 6.2, p. 968 - 972

  摘要：

  DOI：

文献信息

• N-(2,2-Dichloro-2-phenylethylidene)arenesulfonamides in reactions with secondary amines
  作者：I. B. Rozentsveig、G. N. Rozentsveig、A. N. Mirskova、K. A. Chernyshev、L. B. Krivdin、G. G. Levkovskaya

  DOI：10.1134/s1070363208070141

  日期：2008.7

  N-(2,2-Dichloro-2-phenylethylidene)arenesulfonamides were synthesized by a modified procedure, and their reactions with secondary amines were studied for the first time. Reactions of imines with dialkylamines proceed at room temperature to afford alpha,alpha-dichloromethylbenzene and N,N-dialkyl-N'-(arenesulfonyl)formamidines arising from the haloform cleavage of the initially formed unstable N-(1-dialkylamino-2,2-dichloro-2-phenylethyl)arenesulfonamides. When the reaction is carried out upon cooling to 0 degrees C, the products of the nucleophilic addition of secondary amines to azomethines, N-(1-dialkylamino-2,2-dichloro-2-phenylethyl) are formed in yields of no higher than 5%. Nonempirical calculations of C-13-H-1 spin-spin coupling constants and their experimental measurements for the series of the synthesized N-arenesulfonamides were performed to show that these compounds exist in solutions exclusively as E isomers. Preferable conformations of the investigated compounds and the relative energies of their E and Z isomers in the gas phase were determined by quantum-chemical calculations at the MP2/6-311G** level of theory. The NMR spectral data revealed restricted rotation of the N,N-dialkylamino group about the partially double C-NAlk(2) bond in the molecules of N-arenesulfonylformamidines.
• ——
  作者：T. I. Drozdova、A. N. Mirskova

  DOI：10.1023/a:1012457430488

  日期：——

  N-[1-4-Methoxyphenyl-2-phenyl-2,2-dichloroethyl]arenesulfonamides are formed in reaction of N-(2-phenyl,-2.2-dichloroethylidene)-4-chlorobenzenesulfonamide and N-(2-phenyl-2,2-dichloroethylidene)-4-methylbenzenesulfonamide with anisole catalyzed by boron trifluoride etherate, and in reaction of anisole with 1,1-di(arenesulfonamido)-2-phenyl-2,2,-dichloroethanes in the presence of concentrated sulfuric acid.
• Drozdova, T. I.; Levkovskaya, G. G.; Mirskova, A. N., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 6.2, p. 968 - 972
  作者：Drozdova, T. I.、Levkovskaya, G. G.、Mirskova, A. N.

  DOI：——

  日期：——