N-(p-toluenesulfonyl)-p-nitrobenzenesulfonimidamide | 1246403-68-8

• 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-(p-toluenesulfonyl)-p-nitrobenzenesulfonimidamide
• 英文别名: N-[amino-(4-nitrophenyl)-oxo-lambda6-sulfanylidene]-4-methylbenzenesulfonamide；N-[amino-(4-nitrophenyl)-oxo-λ6-sulfanylidene]-4-methylbenzenesulfonamide
• CAS: 1246403-68-8
• 化学式: C₁₃H₁₃N₃O₅S₂
• 分子量: 355.395
• InChiKey: YAVXDRNOTMPNNG-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：

  1-庚烯 、 N-(p-toluenesulfonyl)-p-nitrobenzenesulfonimidamide 在 亚碘酰苯 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 作用下， 以 乙腈 为溶剂， 以92%的产率得到N-[N-(p-toluenesulfonyl)-p-nitrobenzenesulfonimidoyl]-2-pentylaziridine
  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
• 作为产物：
  描述：

  N-(p-toluenesulfonyl)-p-nitrobenzenesulfonimidoyl chloride 在 氨 作用下， 以 乙腈 为溶剂， 以4.6 g的产率得到N-(p-toluenesulfonyl)-p-nitrobenzenesulfonimidamide
  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 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.