(1S,5S,7R)-7-benzyloxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-3-carboxylic acid methyl ester | 1155303-19-7

• 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-6,8-dioxa-3-azabicyclo[3.2.1]octane-3-carboxylic acid methyl ester
• 英文别名: methyl (1S,5S,7R)-7-(phenylmethoxymethyl)-6,8-dioxa-3-azabicyclo[3.2.1]octane-3-carboxylate
• CAS: 1155303-19-7
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: XBBYENSROVUGON-MJBXVCDLSA-N

物化性质

• 沸点：
  420.2±45.0 °C(predicted)
• 密度：
  1.230±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,5S,7R)-7-benzyloxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane-3-carboxylic acid methyl ester 在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以94%的产率得到(1S,5S,7R)-7-benzyloxymethyl-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
• 作为产物：
  描述：

  (4S,5R)-(5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-(2,2-dimethoxyethyl)carbamic acid methyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以66%的产率得到(1S,5S,7R)-7-benzyloxymethyl-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

文献信息

• N-Substituent effects on the diethylzinc addition to benzaldehyde catalysed by bicyclic 1,4-amino alcohols
  作者：Dina Scarpi、Ernesto G. Occhiato、Antonio Guarna

  DOI：10.1016/j.tetasy.2009.01.021

  日期：2009.2

  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.