(1R,5R,7R)-7-benzyloxymethyl-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-3-carboxylic acid methyl ester | 1155303-13-1

• 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: (1R,5R,7R)-7-benzyloxymethyl-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-3-carboxylic acid methyl ester
• CAS: 1155303-13-1
• 化学式: C₁₅H₁₇NO₆
• 分子量: 307.303
• InChiKey: LFTIXRWPIVHSLZ-JHJVBQTASA-N

物化性质

• 熔点：
  76-77 °C
• 沸点：
  497.8±45.0 °C(predicted)
• 密度：
  1.308±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (4R,5R)-(5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolane-4-carbonyl)-(2,2-dimethoxyethyl)carbamic acid methyl ester 在 silica-gel-supported sulfuric acid 作用下， 以 甲苯 为溶剂， 以14%的产率得到(1R,5R,7R)-7-benzyloxymethyl-2-oxo-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