1-(4-nitrobenzenesulfonyl)-2-phenethyl-3-phenylaziridine | 1191292-60-0

• 分子结构分类: 有机化合物
• 英文名称: 1-(4-nitrobenzenesulfonyl)-2-phenethyl-3-phenylaziridine
• 英文别名: 1-(4-nitro-benzenesulfonyl)-2-phenylethyl-3-phenyl-aziridine
• CAS: 1191292-60-0
• 化学式: C₂₂H₂₀N₂O₄S
• 分子量: 408.478
• InChiKey: QPBFCKQSNHMKIW-WELAQSEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-phenylethylstyrene 、 [N-(nosyl)imino]phenyliodinane 在 copper(l) chloride 4A MS 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以51%的产率得到1-(4-nitrobenzenesulfonyl)-2-phenethyl-3-phenylaziridine
  参考文献：
  名称：

  A one-pot stereoselective synthesis of trans-1-aryl-2-aminotetralins from 2-arylethyl styrenes

  摘要：

  An efficient stereoselective synthesis of trans-1-aryl-2-aminotetralins has been achieved via Cu(OTf)(2) catalyzed one-pot aziridination and regioselective intramolecular arylation of in situ generated aziridines from 2-arylethyl styrenes and PhINSO(2)(4-NO(2)C(6)H(4)) [PhINNs]. Reaction of a mixture of E/Z-styrenes (<= 85:15) provided trans-N-protected-1-aryl-2-aminotetralins with high diastereoselectivity (dr > 95:5), which are important synthons for many artificial pharmaceuticals. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.056

文献信息

• A Catalytic and Enantioselective Synthesis of<i>trans-</i>2-Amino-1- aryltetralins
  作者：Saumen Hajra、Biswajit Maji、Dipakranjan Mal

  DOI：10.1002/adsc.200800603

  日期：2009.4

  Abstractmagnified imageThe bis‐oxazoline‐copper complex‐catalyzed aziridination of alkenes followed by an intramolecular Friedel–Crafts alkylation of the tethered andin situgenerated aziridine provides a one‐pot, general and efficient method for the synthesis oftrans‐2‐amino‐1‐aryltetralins from a mixture of 2‐ arylethylstyrenes (E/Z≤85:15) with excellent dia‐ stereo‐ (dr>99:1) and enantioselectivities (up to 92%ee).