(1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]hept-5-ene-3-methylketone | 234451-97-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]hept-5-ene-3-methylketone
• CAS: 234451-97-9
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: JCQFBFRXPRDHPD-MWNCTCPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]hept-5-ene-3-methylketone 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以95%的产率得到(1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]heptane-3-methylketone
  参考文献：
  名称：

  A Theoretical and Experimental Study of the Asymmetric Addition of Dialkylzinc toN-(Diphenylphosphinoyl)benzalimine

  摘要：

  The mechanism of the enantioselective addition of diethylzinc to N(diphenylphosphinoyl)benzalimine with catalysis by bicyclic 2-azanorbornyl-3-methanols was studied by quantum chemical calculations. The mechanism proved to differ from that of the addition of diethylzinc to aldehydes and also from an earlier proposed mechanism. The results of the calculations were used to identify several factors responsible for the selectivity. The theoretical evaluation was performed in connection with an experimental study of the effects of introducing an additional stereocenter in the ligand. An efficient route to both diastereomers of new bicyclic 2-azanorbornyl-3-methanols with an additional chiral center (the secondary alcohol group) is also presented. In the best case, an enantiomeric excess of up to 97% was obtained with these new ligands.

  DOI：

  10.1002/(sici)1521-3765(19990604)5:6<1692::aid-chem1692>3.0.co;2-m
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 (1S,3R,4R)-2-[(S)-1-Phenylethylamino]-2-azabicyclo[2.2.1]hept-5-ene-3-methylketone
  参考文献：
  名称：

  A Theoretical and Experimental Study of the Asymmetric Addition of Dialkylzinc toN-(Diphenylphosphinoyl)benzalimine

  摘要：

  The mechanism of the enantioselective addition of diethylzinc to N(diphenylphosphinoyl)benzalimine with catalysis by bicyclic 2-azanorbornyl-3-methanols was studied by quantum chemical calculations. The mechanism proved to differ from that of the addition of diethylzinc to aldehydes and also from an earlier proposed mechanism. The results of the calculations were used to identify several factors responsible for the selectivity. The theoretical evaluation was performed in connection with an experimental study of the effects of introducing an additional stereocenter in the ligand. An efficient route to both diastereomers of new bicyclic 2-azanorbornyl-3-methanols with an additional chiral center (the secondary alcohol group) is also presented. In the best case, an enantiomeric excess of up to 97% was obtained with these new ligands.

  DOI：

  10.1002/(sici)1521-3765(19990604)5:6<1692::aid-chem1692>3.0.co;2-m