(4R,5R)-5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolane-4-carboxylic acid (2,2-dimethoxyethyl)amide | 1155303-09-5

• 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: (4R,5R)-5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolane-4-carboxylic acid (2,2-dimethoxyethyl)amide
• CAS: 1155303-09-5
• 化学式: C₁₈H₂₇NO₆
• 分子量: 353.415
• InChiKey: SGNHFEVBFYPNRH-GDBMZVCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  75.25
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolane-4-carboxylic acid (2,2-dimethoxyethyl)amide 在 dimethyl sulfide borane 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 2.0h， 以32%的产率得到(4S,5R)-(5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-ylmethyl)-(2,2-dimethoxyethyl)amine
  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：

  (4R,5R)-5-hydroxymethyl-2,2-dimethyl[1,3]dioxolane-4-carboxylic acid (2,2-dimethoxyethyl)amide 、 溴甲苯 在 氢氧化钾 、 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 以2.86 g的产率得到(4R,5R)-5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolane-4-carboxylic acid (2,2-dimethoxyethyl)amide
  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.