dodecanoyl-p-aminophenyl β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dodecanoyl-p-aminophenyl β-D-galactopyranoside
• 英文别名: dodecanoylaminophenol-β-D-galactopyranoside；N-[4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]dodecanamide
• 化学式: C₂₄H₃₉NO₇
• 分子量: 453.576
• InChiKey: XEURJKVDTSBFGN-HYPCABPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-硝基苯基-D-吡喃葡糖苷 在 10percent Pd/C 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 生成 dodecanoyl-p-aminophenyl β-D-galactopyranoside
  参考文献：
  名称：

  Spectral Characterization of Self-Assemblies of Aldopyranoside Amphiphilic Gelators: What is the Essential Structural Difference Between Simple Amphiphiles and Bolaamphiphiles?

  摘要：

  An aldopyranoside-based gelators (dodecanoyl-p-aminophenyl-beta-D-aldopyranoside)s and [1,12-dodecanedicarboxylic-bis(p-aminophenyl-beta-D-aldopyranoside)]s 1-4 were synthesized, and their gelation ability was evaluated in organic solvents and water. Simple aldopyranoside amphiphiles 1 and 2 were found to gelate organic solvents as well as water in the presence of a small amount of alcoholic solvents. More interestingly, not only extremely dilute aqueous solutions (0.05 wt%) of the bolaamphiphiles 3 and 4, but solutions of 3 and 4 in several organic solvents could be gelatinized. These results indicate that 1-4 can act as versatile amphiphilic gelators. We characterized the superstructures of the aqueous gels and organogels prepared from 1-4 using SEM, TEM, NMR and IR spectroscopy, and XRD. The aqueous gels 1 and 2 formed a three-dimensional network of puckered fibrils diameters in the range 20-200 nm, whereas the aqueous gels 3 and 4 produced filmlike lamellar structures with 50-100 nm thickness at extremely low concentrations (0.05 wt%). Powder XRD experiments indicate that the aqueous gels 1 and 2 maintain an interdigitated bilayer structure with a 2.90 nm period with the alkyl chain tilted, while the organogels 1 and 2 take a loosely interdigitated bi-layer structure with a 3.48 = period. On the other hand, the aqueous- and the organogels 3 and 4 have 3,58 nm spacing, which corresponds to a monolayered structure. The XRD, H-1 NMR and FT-IR results suggest that 1-4 are stabilized by a combination of the hydrogen-bonding, pi-pi interactions and hydrophobic forces.

  DOI：

  10.1002/1521-3765(20020617)8:12<2684::aid-chem2684>3.0.co;2-z

文献信息

• Spectral Characterization of Self-Assemblies of Aldopyranoside Amphiphilic Gelators: What is the Essential Structural Difference Between Simple Amphiphiles and Bolaamphiphiles?
  作者：Jong Hwa Jung、Seiji Shinkai、Toshimi Shimizu

  DOI：10.1002/1521-3765(20020617)8:12<2684::aid-chem2684>3.0.co;2-z

  日期：2002.6.17

  An aldopyranoside-based gelators (dodecanoyl-p-aminophenyl-beta-D-aldopyranoside)s and [1,12-dodecanedicarboxylic-bis(p-aminophenyl-beta-D-aldopyranoside)]s 1-4 were synthesized, and their gelation ability was evaluated in organic solvents and water. Simple aldopyranoside amphiphiles 1 and 2 were found to gelate organic solvents as well as water in the presence of a small amount of alcoholic solvents. More interestingly, not only extremely dilute aqueous solutions (0.05 wt%) of the bolaamphiphiles 3 and 4, but solutions of 3 and 4 in several organic solvents could be gelatinized. These results indicate that 1-4 can act as versatile amphiphilic gelators. We characterized the superstructures of the aqueous gels and organogels prepared from 1-4 using SEM, TEM, NMR and IR spectroscopy, and XRD. The aqueous gels 1 and 2 formed a three-dimensional network of puckered fibrils diameters in the range 20-200 nm, whereas the aqueous gels 3 and 4 produced filmlike lamellar structures with 50-100 nm thickness at extremely low concentrations (0.05 wt%). Powder XRD experiments indicate that the aqueous gels 1 and 2 maintain an interdigitated bilayer structure with a 2.90 nm period with the alkyl chain tilted, while the organogels 1 and 2 take a loosely interdigitated bi-layer structure with a 3.48 = period. On the other hand, the aqueous- and the organogels 3 and 4 have 3,58 nm spacing, which corresponds to a monolayered structure. The XRD, H-1 NMR and FT-IR results suggest that 1-4 are stabilized by a combination of the hydrogen-bonding, pi-pi interactions and hydrophobic forces.