3,5-bis[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxymethyl]aniline | 494211-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-bis[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxymethyl]aniline
• CAS: 494211-70-0
• 化学式: C₃₂H₄₇NO₁₂
• 分子量: 637.725
• InChiKey: VORUWDBWEXGMCM-QACPWNKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  对苯二甲酰氯 、 3,5-bis[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxymethyl]aniline 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以70%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：

  5-硝基异酞酰氯 在 ammonium hydroxide 、 sodium tetrahydroborate 、 三溴化磷 、 sodium hydride 、 iron(II) sulfate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二乙二醇二甲醚 、 水 为溶剂， 反应 35.0h， 生成 3,5-bis[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxymethyl]aniline
  参考文献：
  名称：

  内部功能化手性树状聚合物的权宜之计：结合呋喃糖苷骨架的树状分子的合成。

  摘要：

  在一种手性树突状分子的方法中，通过使用1,2：5,6-二异亚丙基葡萄糖作为1,2,5,6-二异亚丙基葡萄糖在1，3，5-三取代的芳族核上构建在内部结合戊糖单元并在外围结合己糖单元的树状聚合物。碳水化合物前体和3，5-二取代的芳族单元作为支链嵌段。碳水化合物部分还以呋喃糖苷环的半缩醛部分的形式提供内部功能。

  DOI：

  10.1021/jo0264168

文献信息

• An Expedient Approach to Internally Functionalized Chiral Dendrimers:  Synthesis of a Dendritic Molecule Incorporating Furanoside Skeleton
  作者：Subir Ghorai、Anup Bhattacharjya、Ajoy Basak、Abhijit Mitra、R. Thomas Williamson

  DOI：10.1021/jo0264168

  日期：2003.1.1

  an approach to chiral dendritic molecules, a dendrimer incorporating pentose units in the interior and hexose units in the periphery is built up on a 1, 3, 5-trisubstituted aromatic core by using 1,2:5,6-diisopropylidene glucose as the carbohydrate precursor and a 3, 5-disubstituted aromatic unit as the branching block. The carbohydrate moiety also provides internal functionalities in the form of hemiacetal

  在一种手性树突状分子的方法中，通过使用1,2：5,6-二异亚丙基葡萄糖作为1,2,5,6-二异亚丙基葡萄糖在1，3，5-三取代的芳族核上构建在内部结合戊糖单元并在外围结合己糖单元的树状聚合物。碳水化合物前体和3，5-二取代的芳族单元作为支链嵌段。碳水化合物部分还以呋喃糖苷环的半缩醛部分的形式提供内部功能。
• A Tetrameric Sugar-Based Azobenzene That Gels Water at Various pH Values and in the Presence of Salts
  作者：Aasheesh Srivastava、Subir Ghorai、Anup Bhattacharjya、Santanu Bhattacharya

  DOI：10.1021/jo050297p

  日期：2005.8.1

  [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.