N-[amino-(4-methylphenyl)-oxo-lambda6-sulfanylidene]-4-nitrobenzenesulfonamide | 1246403-73-5

• 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-methylphenyl)-oxo-lambda6-sulfanylidene]-4-nitrobenzenesulfonamide
• 英文别名: N-[amino-(4-methylphenyl)-oxo-λ6-sulfanylidene]-4-nitrobenzenesulfonamide
• CAS: 1246403-73-5
• 化学式: C₁₃H₁₃N₃O₅S₂
• 分子量: 355.395
• InChiKey: QPCLQNJUKMIZTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 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：
  152
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苯乙烯 、 N-[amino-(4-methylphenyl)-oxo-lambda6-sulfanylidene]-4-nitrobenzenesulfonamide 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 亚碘酰苯 作用下， 以 乙腈 为溶剂， 以60%的产率得到N-[(4-methylphenyl)-oxo-(2-phenylaziridin-1-yl)-lambda6-sulfanylidene]-4-nitrobenzenesulfonamide
  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

• SIAPhos: Phosphorylated Sulfonimidamides and their Use in Iridium‐Catalyzed Asymmetric Hydrogenations of Sterically Hindered Cyclic Enamides
  作者：Frederic W. Patureau、Christin Worch、Maxime A. Siegler、Anthony L. Spek、Carsten Bolm、Joost N. H. Reek

  DOI：10.1002/adsc.201100692

  日期：2012.1

  Phosphorylated sulfonimidamides (SIAPhos) undergo ion exchange reactions with cationic complexes, [Rh(cod)2BF4] and [Ir(cod)2BarF], or neutral complexes [Rh(cod)Cl]2 and [Ir(cod)Cl]2, leading to unprecedented neutral complexes with P‐N‐S‐N chelates. Use of the resulting neutral iridium complexes in asymmetric hydrogenation reactions of tri‐ and tetrasubstituted enamides leads to products with high

  磷酸化的磺酰亚胺酰胺（SIAPhos）与阳离子络合物[Rh（cod）2 BF 4 ]和[Ir（cod）2 BarF]或中性络合物[Rh（cod）Cl] 2和[Ir（cod）Cl ]进行离子交换反应] 2，导致与P‐N‐S‐N螯合物形成前所未有的中性配合物。在三取代和四取代的酰胺的不对称加氢反应中使用所得的中性铱络合物，可得到具有高对映选择性（最高ee为92％）的产物。
• 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.