(3aR,3a'R,3a''R,3a'''R,5S,5'S,5''S,5'''S,6R,6aR,6'R,6a'R,6''R,6a''R,6'''R,6a'''R)-6,6',6'',6'''-(((((E)-diazene-1,2-diyl)bis(benzene-5,1,3-triyl))tetrakis(methylene))tetrakis(oxy))tetrakis(2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylic acid) | 864951-32-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3aR,3a'R,3a''R,3a'''R,5S,5'S,5''S,5'''S,6R,6aR,6'R,6a'R,6''R,6a''R,6'''R,6a'''R)-6,6',6'',6'''-(((((E)-diazene-1,2-diyl)bis(benzene-5,1,3-triyl))tetrakis(methylene))tetrakis(oxy))tetrakis(2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylic acid)
• CAS: 864951-32-6
• 化学式: C₄₈H₅₈N₂O₂₄
• 分子量: 1046.99
• InChiKey: RDHPEAZBODTVIF-VGMOJANDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  74.0
• 可旋转键数：
  18.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  321.6
• 氢给体数：
  4.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  (3aR,3a'R,3a''R,3a'''R,5S,5'S,5''S,5'''S,6R,6aR,6'R,6a'R,6''R,6a''R,6'''R,6a'''R)-6,6',6'',6'''-(((((E)-diazene-1,2-diyl)bis(benzene-5,1,3-triyl))tetrakis(methylene))tetrakis(oxy))tetrakis(2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylic acid) 、 正丁醇 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以75%的产率得到
  参考文献：
  名称：

  A Tetrameric Sugar-Based Azobenzene That Gels Water at Various pH Values and in the Presence of Salts

  摘要：

  [GRAPHICS]A novel low-molecular mass tetrameric sugar derivative containing azobenzene core, 1, showed pronounced hydrogelation at micromolar concentration. Based on this observation, four related azobenzene based tetrameric sugar derivatives, 4-7, and three tetrameric sugar derivatives with a bis-terephthalamide core, 9-11, were also synthesized. However, none of these closely related analogues of the compound 1 showed effective gelation. The gel formed from 1 was characterized extensively using melting temperature analysis, UV-vis, FT-IR, circular dichroism spectroscopy, and scanning electron microscopy. The resultant gel exhibited impressive tolerance to the pH variation of the aqueous phase and gelated water in the pH range of 4-10. While UV-vis and CD spectroscopy indicated that pronounced aggregation of the azobenzene chromophores in 1 was responsible for gelation, FT-IR studies showed that hydrogen bonding is also a contributing factor in the gelation process. The melting of gel was found to depend on the pH of the aqueous medium in which gel was formed. The gel showed considerable photostability to IN irradiation, indicating tight intermolecular packing inside the gelated state that rendered azobenzene groups in the resultant aggregate refractory to photoisomerization. The electron micrographs of the aqueous gels of 1 showed the existence of spongy globular aggregates in such gelated materials. Addition of salts to the aqueous medium led to a delay in the gelation process and also caused remarkable morphological changes in the microstructure of the gel.

  DOI：

  10.1021/jo050297p
• 作为产物：
  描述：

  在 氢氧化钾 、 silver nitrate 作用下， 以 乙醇 、 水 为溶剂， 以1.00 g的产率得到(3aR,3a'R,3a''R,3a'''R,5S,5'S,5''S,5'''S,6R,6aR,6'R,6a'R,6''R,6a''R,6'''R,6a'''R)-6,6',6'',6'''-(((((E)-diazene-1,2-diyl)bis(benzene-5,1,3-triyl))tetrakis(methylene))tetrakis(oxy))tetrakis(2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylic acid)
  参考文献：
  名称：

  A Tetrameric Sugar-Based Azobenzene That Gels Water at Various pH Values and in the Presence of Salts

  摘要：

  [GRAPHICS]A novel low-molecular mass tetrameric sugar derivative containing azobenzene core, 1, showed pronounced hydrogelation at micromolar concentration. Based on this observation, four related azobenzene based tetrameric sugar derivatives, 4-7, and three tetrameric sugar derivatives with a bis-terephthalamide core, 9-11, were also synthesized. However, none of these closely related analogues of the compound 1 showed effective gelation. The gel formed from 1 was characterized extensively using melting temperature analysis, UV-vis, FT-IR, circular dichroism spectroscopy, and scanning electron microscopy. The resultant gel exhibited impressive tolerance to the pH variation of the aqueous phase and gelated water in the pH range of 4-10. While UV-vis and CD spectroscopy indicated that pronounced aggregation of the azobenzene chromophores in 1 was responsible for gelation, FT-IR studies showed that hydrogen bonding is also a contributing factor in the gelation process. The melting of gel was found to depend on the pH of the aqueous medium in which gel was formed. The gel showed considerable photostability to IN irradiation, indicating tight intermolecular packing inside the gelated state that rendered azobenzene groups in the resultant aggregate refractory to photoisomerization. The electron micrographs of the aqueous gels of 1 showed the existence of spongy globular aggregates in such gelated materials. Addition of salts to the aqueous medium led to a delay in the gelation process and also caused remarkable morphological changes in the microstructure of the gel.

  DOI：

  10.1021/jo050297p