6-deoxy-6-(1-imidazolyl)-2,4:3,5-dimethylene-N-n-octyl-D-gluconamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 6-deoxy-6-(1-imidazolyl)-2,4:3,5-dimethylene-N-n-octyl-D-gluconamide
• 英文别名: (4R,4aS,8R,8aR)-8-(imidazol-1-ylmethyl)-N-octyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine-4-carboxamide
• 化学式: C₁₉H₃₁N₃O₅
• 分子量: 381.472
• InChiKey: MVYXORHLNVYUNH-ZJPYXAASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  83.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4:3,5-dimethylene-N-n-octyl-D-gluconamide 在 吡啶 作用下， 以 氯仿 为溶剂， 50.0 ℃ 、1500.0 MPa 条件下， 反应 49.0h， 生成 6-deoxy-6-(1-imidazolyl)-2,4:3,5-dimethylene-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

• Hafkamp, Rudi J. H.; Feiters, Martinus C.; Nolte, Rocland J. M., Angewandte Chemie, 1994, vol. 106, # 9, p. 1054 - 1055
  作者：Hafkamp, Rudi J. H.、Feiters, Martinus C.、Nolte, Rocland J. M.

  DOI：——

  日期：——
• 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.