(+)-(1R,2S,3R)-3-[N-phenylsulfonyl-N-(3,5-dimethylphenyl)amino]-2-bornanyl 2-(trifluoromethyl)acrylate | 653595-54-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-(1R,2S,3R)-3-[N-phenylsulfonyl-N-(3,5-dimethylphenyl)amino]-2-bornanyl 2-(trifluoromethyl)acrylate
• 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-(trifluoromethyl)prop-2-enoate
• CAS: 653595-54-1
• 化学式: C₂₈H₃₂F₃NO₄S
• 分子量: 535.628
• InChiKey: GZSIVHLKUACSTI-UDFVPUEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (+)-(1R,2S,3R)-3-[N-phenylsulfonyl-N-(3,5-dimethylphenyl)amino]-2-bornanyl 2-(trifluoromethyl)acrylate 在 溶剂黄146 、 calcium oxide 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 2-(Ethoxycarbonylamino-methyl)-3,3,3-trifluoro-propionic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester
  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：

  2-(trifluoromethyl)acrylic chloride 、 (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 作用下， 生成 (+)-(1R,2S,3R)-3-[N-phenylsulfonyl-N-(3,5-dimethylphenyl)amino]-2-bornanyl 2-(trifluoromethyl)acrylate
  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.