(1S,5S,7R)-7-hydroxymethyl-6,8-dioxa-3-azabicyclo-[3.2.1]octane-3-carboxylic acid methyl ester | 1155303-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡咯
• 英文名称: (1S,5S,7R)-7-hydroxymethyl-6,8-dioxa-3-azabicyclo-[3.2.1]octane-3-carboxylic acid methyl ester
• CAS: 1155303-46-0
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: BPAYWUUFUAMKAO-XVMARJQXSA-N

物化性质

• 沸点：
  336.7±42.0 °C(predicted)
• 密度：
  1.334±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  68.23
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (1S,5S,7R)-7-benzyloxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-3-carboxylic acid methyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 18.0h， 以84%的产率得到(1S,5S,7R)-7-hydroxymethyl-6,8-dioxa-3-azabicyclo-[3.2.1]octane-3-carboxylic acid methyl ester
  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