2-methoxy-N-n-octyl-D-gluconamide | 220551-63-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-methoxy-N-n-octyl-D-gluconamide
• 英文别名: (2R,3S,4R,5R)-3,4,5,6-tetrahydroxy-2-methoxy-N-octylhexanamide
• CAS: 220551-63-3
• 化学式: C₁₅H₃₁NO₆
• 分子量: 321.414
• InChiKey: GGTKCPCRFQHADK-YIYPIFLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 2-methoxy-N-n-octyl-D-gluconamide 在 吡啶 作用下， 反应 2.0h， 生成 2-methoxy-N-n-octyl-D-gluconamide-6-benzoate
  参考文献：
  名称：

  Organogels from Carbohydrate Amphiphiles

  摘要：

  Gluconamides can be easily functionalized to give a variety of compounds that form organogels with a high viscosity. N-n-octyl-D-gluconamide-6-benzoate gelates a large variety of organic solvents, including 1,2-xylene, chloroform, ethyl acetate, and ethanol, to form gels which are, in some cases, stable even above the boiling point of the pure solvent; The 2-methoxy, 6-imidazolyl, 6-acetyl, and 6-cyclohexanoyl derivatives also show gelation, but the 2,4;3,5-dimethylene-protected derivatives do not. Detailed H-1 NMR, TR, and X-ray powder diffraction studies reveal that the molecules of most gelators are packed in a head-to-tail fashion. If there is, however, the possibility to form interlayer hydrogen bonds, as in the case of N-n-octyl-D-gluconamide or N-n-octyl-D-gluconamide-6-(3-pyridyl carboxylate), the molecules are packed head-to-head. Some gluconamides, e.g., those with aliphatic substituents, express their molecular chirality in the supramolecular structures, whereas others, in particular those containing a large aromatic substituent on carbon atom C-6, yield nonchiral aggregates, probably due to interfering pi-pi stacking interactions of the substituents. DSC experiments show that the formation of the gels is an entropy-driven process.

  DOI：

  10.1021/jo981158t
• 作为产物：
  描述：

  N-辛基-D-谷氨酰胺 、 硫酸二甲酯 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以14%的产率得到2-methoxy-N-n-octyl-D-gluconamide
  参考文献：
  名称：

  Organogels from Carbohydrate Amphiphiles

  摘要：

  Gluconamides can be easily functionalized to give a variety of compounds that form organogels with a high viscosity. N-n-octyl-D-gluconamide-6-benzoate gelates a large variety of organic solvents, including 1,2-xylene, chloroform, ethyl acetate, and ethanol, to form gels which are, in some cases, stable even above the boiling point of the pure solvent; The 2-methoxy, 6-imidazolyl, 6-acetyl, and 6-cyclohexanoyl derivatives also show gelation, but the 2,4;3,5-dimethylene-protected derivatives do not. Detailed H-1 NMR, TR, and X-ray powder diffraction studies reveal that the molecules of most gelators are packed in a head-to-tail fashion. If there is, however, the possibility to form interlayer hydrogen bonds, as in the case of N-n-octyl-D-gluconamide or N-n-octyl-D-gluconamide-6-(3-pyridyl carboxylate), the molecules are packed head-to-head. Some gluconamides, e.g., those with aliphatic substituents, express their molecular chirality in the supramolecular structures, whereas others, in particular those containing a large aromatic substituent on carbon atom C-6, yield nonchiral aggregates, probably due to interfering pi-pi stacking interactions of the substituents. DSC experiments show that the formation of the gels is an entropy-driven process.

  DOI：

  10.1021/jo981158t

文献信息

• Organogels from Carbohydrate Amphiphiles
  作者：Rudi J. H. Hafkamp、Martinus C. Feiters、Roeland J. M. Nolte

  DOI：10.1021/jo981158t

  日期：1999.1.1

  Gluconamides can be easily functionalized to give a variety of compounds that form organogels with a high viscosity. N-n-octyl-D-gluconamide-6-benzoate gelates a large variety of organic solvents, including 1,2-xylene, chloroform, ethyl acetate, and ethanol, to form gels which are, in some cases, stable even above the boiling point of the pure solvent; The 2-methoxy, 6-imidazolyl, 6-acetyl, and 6-cyclohexanoyl derivatives also show gelation, but the 2,4;3,5-dimethylene-protected derivatives do not. Detailed H-1 NMR, TR, and X-ray powder diffraction studies reveal that the molecules of most gelators are packed in a head-to-tail fashion. If there is, however, the possibility to form interlayer hydrogen bonds, as in the case of N-n-octyl-D-gluconamide or N-n-octyl-D-gluconamide-6-(3-pyridyl carboxylate), the molecules are packed head-to-head. Some gluconamides, e.g., those with aliphatic substituents, express their molecular chirality in the supramolecular structures, whereas others, in particular those containing a large aromatic substituent on carbon atom C-6, yield nonchiral aggregates, probably due to interfering pi-pi stacking interactions of the substituents. DSC experiments show that the formation of the gels is an entropy-driven process.