(1R,2S)-N-(p-nitrobenzenesulfonyl)amino-1,2,3,4-tetrahydro-6-acetoxynaphthalen-1,2-imine | 1262722-79-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1R,2S)-N-(p-nitrobenzenesulfonyl)amino-1,2,3,4-tetrahydro-6-acetoxynaphthalen-1,2-imine
• CAS: 1262722-79-1
• 化学式: C₁₈H₁₆N₂O₆S
• 分子量: 388.401
• InChiKey: ZWFCYEPYPDEBCL-PAMZHZACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  7,8-dihydronaphthalen-2-yl acetate 、 [N-(nosyl)imino]phenyliodinane 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 (S,S)-N,N-bis(2,6-dichlorobenzylidene)cyclohexan-1,2-diamine 作用下， 以 二氯甲烷 为溶剂， 反应 48.25h， 生成 (1R,2S)-N-(p-nitrobenzenesulfonyl)amino-1,2,3,4-tetrahydro-6-acetoxynaphthalen-1,2-imine 、 (1S,2R)-N-(p-nitrobenzenesulfonyl)amino-1,2,3,4-tetrahydro-6-acetoxynaphthalen-1,2-imine
  参考文献：
  名称：

  Asymmetric catalytic aziridination of dihydronaphthalenes for the preparation of substituted 2-aminotetralins

  摘要：

  An enantioselective synthesis of substituted 2-aminotetralins from dihydronaphthalenes in four steps is described. The key step is the Jacobsen's (diimine)copper-catalyzed asymmetric aziridination of dihydronaphthalenes to the respective aziridines in 33-82% yields and 60-87% enantiomeric excess. The enantioselectivity and the yield were dependent on the properties of the nitrene precursor. pTs=NIPh appeared in general to give better results than pNsN=IPh. Aziridines were ring-opened in the benzylic position by catalytic hydrogenolysis in quantitative yields, and deprotected in two steps to the respective 2-aminotetralins in 66-85% yields. The synthesis of (S)-2-aminotetralin (>98% ee) and (S)-2-amino-7-methoxytetralin (56% ee) were accomplished in 30 and 52% overall yields, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.010