N-[amino-(4-chlorophenyl)-oxo-lambda6-sulfanylidene]-4-methylbenzenesulfonamide | 1246403-75-7

• 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-[amino-(4-chlorophenyl)-oxo-lambda6-sulfanylidene]-4-methylbenzenesulfonamide
• 英文别名: N-[amino-(4-chlorophenyl)-oxo-λ6-sulfanylidene]-4-methylbenzenesulfonamide
• CAS: 1246403-75-7
• 化学式: C₁₃H₁₃ClN₂O₃S₂
• 分子量: 344.843
• InChiKey: ALRJDBBUNXIKBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙基苯 、 N-[amino-(4-chlorophenyl)-oxo-lambda6-sulfanylidene]-4-methylbenzenesulfonamide 在 碘苯二乙酸 、 (hydrotris(4-bromo-3,5-dimethyl)pyrazolyl borate)Ag 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以35%的产率得到
  参考文献：
  名称：

  Catalytic C–H amination of alkanes with sulfonimidamides: silver(I)-scorpionates vs. dirhodium(II) carboxylates

  摘要：

  The silver complex [Tp*Ag-,Ag-Br](2) (Tp*(,Br): hydrotris(4-bromo-3,5-dimethyl)pyrazolyl borate) and the rhodium complex Rh-2(S-nta)(4) (nta: N-(1,8-naphthoyl)-alanine) are competent catalysts for C-H bond functionalization by nitrene insertion. Both complexes display similar catalytic activity for the functionalization of benzylic C-H bonds, although the silver derivative does not provide the very high diastereoselection induced by the rhodium complex. On the other hand, when starting from 5 equiv of alkanes, such as pentane and other C-6-C-8 branched non-activated hydrocarbons, it is the silver catalyst that promotes the amination of the C-H bonds with yields of up to 70%, higher than those provided by the rhodium counterpart. When available, the tertiary C-H bonds of the substrate are preferentially derivatized, as a consequence of a stepwise mechanism in which carbon-centered radicals are involved. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.005
• 作为产物：
  描述：

  N-tosyl-4-chlorobenzenesulfonimidoyl chloride 在 氨 作用下， 以 乙腈 为溶剂， 生成 N-[amino-(4-chlorophenyl)-oxo-lambda6-sulfanylidene]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Catalytic stereoselective alkene aziridination with sulfonimidamides

  摘要：

  Diastereoselective copper-catalyzed alkene aziridination has been investigated using chiral nitrenes generated from sulfonimidamides in the presence of an iodine(III) oxidant. Starting from a stoichiometric amount of the substrates, the corresponding aziridines were isolated with excellent yields of up to 96%. Good levels of asymmetric induction were obtained in the case of electron-poor olefins, with an optimal de of 94% being reached starting from tert-butyl acrylate. Matching and mismatching effects were also observed upon the use of chiral copper catalysts for the aziridination of styrene. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.032

文献信息

• Catalytic C–H amination of alkanes with sulfonimidamides: silver(I)-scorpionates vs. dirhodium(II) carboxylates
  作者：Álvaro Beltrán、Camille Lescot、M. Mar Díaz-Requejo、Pedro J. Pérez、Philippe Dauban

  DOI：10.1016/j.tet.2013.02.005

  日期：2013.6

  The silver complex [Tp*Ag-,Ag-Br](2) (Tp*(,Br): hydrotris(4-bromo-3,5-dimethyl)pyrazolyl borate) and the rhodium complex Rh-2(S-nta)(4) (nta: N-(1,8-naphthoyl)-alanine) are competent catalysts for C-H bond functionalization by nitrene insertion. Both complexes display similar catalytic activity for the functionalization of benzylic C-H bonds, although the silver derivative does not provide the very high diastereoselection induced by the rhodium complex. On the other hand, when starting from 5 equiv of alkanes, such as pentane and other C-6-C-8 branched non-activated hydrocarbons, it is the silver catalyst that promotes the amination of the C-H bonds with yields of up to 70%, higher than those provided by the rhodium counterpart. When available, the tertiary C-H bonds of the substrate are preferentially derivatized, as a consequence of a stepwise mechanism in which carbon-centered radicals are involved. (C) 2013 Elsevier Ltd. All rights reserved.
• Catalytic stereoselective alkene aziridination with sulfonimidamides
  作者：Fabien Robert-Peillard、Pablo H. Di Chenna、Chungen Liang、Camille Lescot、Florence Collet、Robert H. Dodd、Philippe Dauban

  DOI：10.1016/j.tetasy.2010.03.032

  日期：2010.6

  Diastereoselective copper-catalyzed alkene aziridination has been investigated using chiral nitrenes generated from sulfonimidamides in the presence of an iodine(III) oxidant. Starting from a stoichiometric amount of the substrates, the corresponding aziridines were isolated with excellent yields of up to 96%. Good levels of asymmetric induction were obtained in the case of electron-poor olefins, with an optimal de of 94% being reached starting from tert-butyl acrylate. Matching and mismatching effects were also observed upon the use of chiral copper catalysts for the aziridination of styrene. (C) 2010 Elsevier Ltd. All rights reserved.