(1S,5S,7R)-7-benzyloxymethyl-3-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane | 1155303-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (1S,5S,7R)-7-benzyloxymethyl-3-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane
• CAS: 1155303-28-8
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: GAWYWHYMPLXKPQ-OTWHNJEPSA-N

物化性质

• 熔点：
  64-65 °C
• 沸点：
  462.4±45.0 °C(predicted)
• 密度：
  1.175±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  30.93
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,5S,7R)-7-benzyloxymethyl-3-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane 在 palladium(II) hydroxide/carbon 、 环己烯 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以100%的产率得到(1S,5S,7R)-(3-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]oct-7-yl)methanol
  参考文献：
  名称：

  N-Substituent effects on the diethylzinc addition to benzaldehyde catalysed by bicyclic 1,4-amino alcohols

  摘要：

  Chiral enantiopure bicyclic 1,4-aminoalcohols were synthesised by a new methodology that provided a common precursor, which was easily N-functionalised with a wide variety of substituents. The final compounds were used as chiral ligands in a model study of the enantioselective addition of diethyl zinc to benzaldehyde, aimed at understanding the influence of the N-substituent on both the rate and stereoselectivity of the reaction. This set of experiments also provided interesting insight into the non-catalysed addition that Occurred by employing commercially available Et(2)Zn solutions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.01.021
• 作为产物：
  描述：

  (1S,5S,7R)-7-benzyloxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane 、 苯硼酸 在 氧气 、 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以50%的产率得到(1S,5S,7R)-7-benzyloxymethyl-3-phenyl-6,8-dioxa-3-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  N-Substituent effects on the diethylzinc addition to benzaldehyde catalysed by bicyclic 1,4-amino alcohols

  摘要：

  Chiral enantiopure bicyclic 1,4-aminoalcohols were synthesised by a new methodology that provided a common precursor, which was easily N-functionalised with a wide variety of substituents. The final compounds were used as chiral ligands in a model study of the enantioselective addition of diethyl zinc to benzaldehyde, aimed at understanding the influence of the N-substituent on both the rate and stereoselectivity of the reaction. This set of experiments also provided interesting insight into the non-catalysed addition that Occurred by employing commercially available Et(2)Zn solutions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.01.021