N-[N-(p-toluenesulfonyl)-p-nitrobenzenesulfonimidoyl]-2-methoxycarbonylaziridine | 1246403-42-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[N-(p-toluenesulfonyl)-p-nitrobenzenesulfonimidoyl]-2-methoxycarbonylaziridine
• 英文别名: methyl 1-[N-(4-methylphenyl)sulfonyl-S-(4-nitrophenyl)sulfonimidoyl]aziridine-2-carboxylate
• CAS: 1246403-42-8
• 化学式: C₁₇H₁₇N₃O₇S₂
• 分子量: 439.47
• InChiKey: MMBNNMYVZWQLNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  136.02
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-[N-(p-toluenesulfonyl)-p-nitrobenzenesulfonimidoyl]-2-methoxycarbonylaziridine 在 水 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到methyl 3-hydroxy-2-[N-(p-toluenesulfonyl)-p-nitrobenzenesulfonimidoyl]amino-propionate
  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-nitrobenzenesulfonimidamide 、 丙烯酸甲酯（MA） 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88%的产率得到N-[N-(p-toluenesulfonyl)-p-nitrobenzenesulfonimidoyl]-2-methoxycarbonylaziridine
  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