(1S,5S,7R)-7-benzyloxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane | 1155303-26-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,5S,7R)-7-benzyloxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane
• 英文别名: (1S,5S,7R)-7-(phenylmethoxymethyl)-6,8-dioxa-3-azabicyclo[3.2.1]octane
• CAS: 1155303-26-6
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: WXBZPUFUKOABKG-XQQFMLRXSA-N

物化性质

• 沸点：
  361.9±37.0 °C(predicted)
• 密度：
  1.143±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

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 、 2,2,2-三氟乙基三氟甲烷磺酸酯 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 17.0h， 以65%的产率得到(1S,5S,7R)-7-benzyloxymethyl-3-(2,2,2-trifluoroethyl)-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：

  (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

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.