(1R,2S)-N-(p-methylbenzenesulfonyl)amino-1,2,3,4-tetrahydro-6-acetoxynaphthalen-1,2-imine | 1262722-72-4

• 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: (1R,2S)-N-(p-methylbenzenesulfonyl)amino-1,2,3,4-tetrahydro-6-acetoxynaphthalen-1,2-imine
• 英文别名: [(1aS,7bR)-1-(4-methylphenyl)sulfonyl-1a,2,3,7b-tetrahydronaphtho[1,2-b]azirin-5-yl] acetate
• CAS: 1262722-72-4
• 化学式: C₁₉H₁₉NO₄S
• 分子量: 357.43
• InChiKey: ZNZGCVZTQRTXNF-ABZYKWASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S)-N-(p-methylbenzenesulfonyl)amino-1,2,3,4-tetrahydro-6-acetoxynaphthalen-1,2-imine 在 10% palladium on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 (S)-2-(p-methylbenzenesulfonyl)amino-6-acetoxy-1,2,3,4-tetrahydronaphthalene
  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
• 作为产物：
  描述：

  7,8-dihydronaphthalen-2-yl acetate 、 对甲苯磺酰胺 在 N-溴代丁二酰亚胺(NBS) 、 dirhodium tetrakis(caprolactamate) 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到(1R,2S)-N-(p-methylbenzenesulfonyl)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