(1R,2S,3R)-3-[N-phenylsulfonyl-N-(3,5-dimethylphenyl)amino]-2-bornanyl N-(ethoxycarbonyl)-N-[(4-nitrophenylsulfonyl)oxy]-2-aminomethyl-3,3,3-trifluoropropanoate | 653595-66-5

• 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,3R)-3-[N-phenylsulfonyl-N-(3,5-dimethylphenyl)amino]-2-bornanyl N-(ethoxycarbonyl)-N-[(4-nitrophenylsulfonyl)oxy]-2-aminomethyl-3,3,3-trifluoropropanoate
• 英文别名: [(1R,2S,3R,4S)-3-[N-(benzenesulfonyl)-3,5-dimethylanilino]-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-[[ethoxycarbonyl-(4-nitrophenyl)sulfonyloxyamino]methyl]-3,3,3-trifluoropropanoate
• CAS: 653595-66-5
• 化学式: C₃₇H₄₂F₃N₃O₁₁S₂
• 分子量: 825.881
• InChiKey: OKJLIBRNIITWGE-MYHUQHNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  199
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R)-3-[N-phenylsulfonyl-N-(3,5-dimethylphenyl)amino]-2-bornanyl N-(ethoxycarbonyl)-N-[(4-nitrophenylsulfonyl)oxy]-2-aminomethyl-3,3,3-trifluoropropanoate 在 sodium hydride 作用下， 生成 (+)-1-ethyl 2-(1R,2S,3R)-3-[N-phenylsulfonyl-N-(3,5-dimethylphenyl)amino]-2-bornanyl 2-(trifluoromethyl)aziridine-1,2-dicarboxylate
  参考文献：
  名称：

  Aza-Michael Addition of Nosyloxycarbamates to 2-(Trifluoromethyl)acrylates

  摘要：

  [GRAPHICS]The amination of 2-(trifluoromethyl)acrylates, performed by nosyloxycarbamates, gives two different aminated products, the derivatives of alpha-trifluoromethyl beta-amino esters or the aziridines, in high yields by changing the reaction conditions. The aza-Michael addition product was isolated for the first time in this kind of reaction. This finding confirms the aza-MIRC mechanism we previously proposed. Asymmetric induction was also pursued.

  DOI：

  10.1021/ol0361554
• 作为产物：
  描述：

  (1R,2S,3R)-(+)-3-[N-(苯磺酰)-N-(3,5-二甲基-苯基)氨基]-2-菠烷醇 在 吡啶 、 calcium oxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (1R,2S,3R)-3-[N-phenylsulfonyl-N-(3,5-dimethylphenyl)amino]-2-bornanyl N-(ethoxycarbonyl)-N-[(4-nitrophenylsulfonyl)oxy]-2-aminomethyl-3,3,3-trifluoropropanoate
  参考文献：
  名称：

  Aza-Michael Addition of Nosyloxycarbamates to 2-(Trifluoromethyl)acrylates

  摘要：

  [GRAPHICS]The amination of 2-(trifluoromethyl)acrylates, performed by nosyloxycarbamates, gives two different aminated products, the derivatives of alpha-trifluoromethyl beta-amino esters or the aziridines, in high yields by changing the reaction conditions. The aza-Michael addition product was isolated for the first time in this kind of reaction. This finding confirms the aza-MIRC mechanism we previously proposed. Asymmetric induction was also pursued.

  DOI：

  10.1021/ol0361554

文献信息

• Aza-Michael Addition of Nosyloxycarbamates to 2-(Trifluoromethyl)acrylates
  作者：Daniele Colantoni、Stefania Fioravanti、Lucio Pellacani、Paolo A. Tardella

  DOI：10.1021/ol0361554

  日期：2004.1.1

  [GRAPHICS]The amination of 2-(trifluoromethyl)acrylates, performed by nosyloxycarbamates, gives two different aminated products, the derivatives of alpha-trifluoromethyl beta-amino esters or the aziridines, in high yields by changing the reaction conditions. The aza-Michael addition product was isolated for the first time in this kind of reaction. This finding confirms the aza-MIRC mechanism we previously proposed. Asymmetric induction was also pursued.