(4R,5R)-5-hydroxymethyl-2,2-dimethyl[1,3]dioxolane-4-carboxylic acid (2,2-dimethoxyethyl)amide | 1155303-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-5-hydroxymethyl-2,2-dimethyl[1,3]dioxolane-4-carboxylic acid (2,2-dimethoxyethyl)amide
• CAS: 1155303-07-3
• 化学式: C₁₁H₂₁NO₆
• 分子量: 263.291
• InChiKey: OJKQNWSPNUSMQU-VXNVDRBHSA-N

物化性质

• 沸点：
  433.3±45.0 °C(predicted)
• 密度：
  1.142±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.77
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  86.25
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  D-erythronolactone acetonide 、 氨基乙醛缩二甲醇 在 三甲基铝 、 盐酸 、 水 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 (4R,5R)-5-hydroxymethyl-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.