2,4:3,5-dimethylene-N-n-octyl-D-gluconamide | 162179-09-1

• 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: 2,4:3,5-dimethylene-N-n-octyl-D-gluconamide
• CAS: 162179-09-1
• 化学式: C₁₆H₂₉NO₆
• 分子量: 331.409
• InChiKey: HUSSFJRRVOQVNM-APIJFGDWSA-N

物化性质

• 沸点：
  521.6±50.0 °C(predicted)
• 密度：
  1.116±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  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
• 作为产物：
  描述：

  8-(hydroxymethyl)-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine-4-carboxylic acid 在 acid 作用下， 生成 2,4:3,5-dimethylene-N-n-octyl-D-gluconamide
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes
  作者：Rudi J. H. Hafkamp、Bas P. A. Kokke、Iris M. Danke、Hubertus P. M. Geurts、Alan E. Rowan、Martinus C. Feiters、Roeland J. M. Nolte

  DOI：10.1039/a608266a

  日期：——

  Functionalized gluconamides and their metal complexes are shown to give supramolecular assemblies, in some cases chiral, and to form organogels in a large variety of organic solvents, e.g. methacrylate mixtures which can be polymerized, as well as o-xylene, chloroform, ethyl acetate, ethanol and tetrahydrofuran.

  研究表明，功能化葡糖酰胺及其金属络合物可形成超分子组装体，在某些情况下具有手性，并可在多种有机溶剂中形成有机凝胶，例如可聚合的甲基丙烯酸酯混合物，以及邻二甲苯、氯仿、乙酸乙酯、乙醇和四氢呋喃。