methyl 1-(4-chloro-N-tosylphenylsulfonimidoyl)aziridine-2-carboxylate | 1246403-62-2

• 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: methyl 1-(4-chloro-N-tosylphenylsulfonimidoyl)aziridine-2-carboxylate
• CAS: 1246403-62-2
• 化学式: C₁₇H₁₇ClN₂O₅S₂
• 分子量: 428.917
• InChiKey: ICDSRFOQOPNILT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  92.88
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  N-[amino-(4-chlorophenyl)-oxo-lambda6-sulfanylidene]-4-methylbenzenesulfonamide 、 丙烯酸甲酯（MA） 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 亚碘酰苯 作用下， 以 乙腈 为溶剂， 以50%的产率得到methyl 1-(4-chloro-N-tosylphenylsulfonimidoyl)aziridine-2-carboxylate
  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