(+)-(2R,1'S)-1-tosyl-2-[1'-(dibenzylamino)-2'-phenylethyl]aziridine | 1065519-42-7

• 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: (+)-(2R,1'S)-1-tosyl-2-[1'-(dibenzylamino)-2'-phenylethyl]aziridine
• 英文别名: (1S)-N,N-dibenzyl-1-[(2R)-1-(4-methylphenyl)sulfonylaziridin-2-yl]-2-phenylethanamine
• CAS: 1065519-42-7
• 化学式: C₃₁H₃₂N₂O₂S
• 分子量: 496.673
• InChiKey: KHBOAJFPLKIUGN-BCAKTTGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  48.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氯碘甲烷 、 N-[(2S)-2-(dibenzylamino)-3-phenylpropylidene]-4-methylbenzenesulfonamide 在 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以55%的产率得到(+)-(2R,1'S)-1-tosyl-2-[1'-(dibenzylamino)-2'-phenylethyl]aziridine
  参考文献：
  名称：

  Addition Reactions of Chloro- or Iodomethyllithium to Imines. Synthesis of Enantiopure Aziridines and β-Chloroamines

  摘要：

  We report a novel, simple, and efficient synthesis of aziridines and 1-chloroalkan-2-amines by the reaction of imines derived from various aldehydes and p-toluenesulfonamide or benzenesulfonamide with iodoor chloromethyllithium, respectively. Both halogenated anions were generated in situ by treatment of diiodo- or chloroiodomethane with methyllithium at -78 or 0 degrees C. The reaction of in situ generated iodo- or chloromethyllithium could also be performed from chiral 2-aminoaldimines to yield enantiopure aziridines or (2S,3S)-2,3-diamino-1-chloroalkanes with high stereoselectivity.

  DOI：

  10.1021/jo802596y

文献信息

• Addition Reactions of Iodomethyllithium to Imines. A Direct and Efficient Synthesis of Aziridines and Enantiopure Amino Aziridines
  作者：José M. Concellón、Humberto Rodríguez-Solla、Carmen Simal

  DOI：10.1021/ol801607r

  日期：2008.10.16

  synthesis of aziridines by the reaction of imines derived from p-toluenesulfonamides with in situ generated iodomethyllithium, with a simple and rapid experimental protocol, is reported for the first time. The reaction with the chiral aldimine derived from phenylalaninal allowed access to (2R,1'S)-2-(1'-aminoalkyl)aziridine with very high diastereoselectivity, in enantiopure form. A mechanism to explain

  首次报道了通过对甲苯磺酸酰胺衍生的亚胺与原位生成的碘代甲基锂的有效而普遍的合成，该方法具有简单而快速的实验方案。与衍生自苯丙氨酸的手性醛亚胺的反应允许以对映体纯的形式获得具有非常高非对映选择性的（2R，1'S）-2-（1'-氨基烷基）氮丙啶。提出了解释这种新颖反应的机制。
• Addition Reactions of Chloro- or Iodomethyllithium to Imines. Synthesis of Enantiopure Aziridines and β-Chloroamines
  作者：José M. Concellón、Humberto Rodríguez-Solla、Pablo L. Bernad、Carmen Simal

  DOI：10.1021/jo802596y

  日期：2009.3.20

  We report a novel, simple, and efficient synthesis of aziridines and 1-chloroalkan-2-amines by the reaction of imines derived from various aldehydes and p-toluenesulfonamide or benzenesulfonamide with iodoor chloromethyllithium, respectively. Both halogenated anions were generated in situ by treatment of diiodo- or chloroiodomethane with methyllithium at -78 or 0 degrees C. The reaction of in situ generated iodo- or chloromethyllithium could also be performed from chiral 2-aminoaldimines to yield enantiopure aziridines or (2S,3S)-2,3-diamino-1-chloroalkanes with high stereoselectivity.