1,11-Bis(4-aminophenylthio)-3,6,9-trioxaundecane | 192223-00-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,11-Bis(4-aminophenylthio)-3,6,9-trioxaundecane
• 英文别名: 4-[2-[2-[2-[2-(4-aminophenyl)sulfanylethoxy]ethoxy]ethoxy]ethylsulfanyl]aniline
• CAS: 192223-00-0
• 化学式: C₂₀H₂₈N₂O₃S₂
• 分子量: 408.586
• InChiKey: WGDTWJYRUJOMTH-UHFFFAOYSA-N

物化性质

• 沸点：
  612.1±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  27.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  79.73
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,11-Bis(4-aminophenylthio)-3,6,9-trioxaundecane 在 盐酸 、 氢氧化钾 、 sodium acetate 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 5.25h， 生成 1,11-Bis(4-mercaptophenylthio)-3,6,9-trioxaundecane
  参考文献：
  名称：

  Self-Assembly of Novel [2]Catenanes and [2]Pseudorotaxanes Incorporating Thiacrown Ethers or Their Acyclic Analogues

  摘要：

  AbstractA series of π electron rich macrocyclic polythioethers and their acyclic analogues have been synthesized in good yields. The association constants for the complexation of the π electron deficient bis(hexafluorophosphate) bipyridinium‐based salt, paraquat, by these macrocycles, as well as those for the complexation of corresponding acyclic compounds by the bipyridinium‐based tetracationic cyclophane, cyclobis(paraquat‐p‐phenylene), are significantly lower than those observed in the case of the “all‐oxygen” analogues. Nonetheless, yields as high as 86% were recorded in the template‐directed syntheses of [2]catenanes composed of cyclobis(paraquat‐p‐phenylene) and the macrocyclic polythioethers. Single‐crystal X‐ray crystallographic analyses of the [2]catenanes incorporating constitutionally unsymmetrical π electron rich macrocyclic polythioethers revealed that, in all cases, the dioxyaromatic units are located inside the cavity of the tetracationic cyclophane component in preference to the dithiaaromatic units. A similar selectivity was observed in solution by variable‐temperature 1H NMR spectroscopy. However, inversion of the ratio between the two translational isomers of the two [2]catenanes bearing 1,5‐dithi‐anaphthalene, as one of their π electron rich ring systems, and either 1,4‐dioxy‐benzene or 1,5‐dioxynaphthalene, as the other, occurs upon increasing the temperature from –30 to +30 πC. These [2]catenanes can be viewed as temperature‐responsive molecular switches.

  DOI：

  10.1002/chem.19970030518
• 作为产物：
  描述：

  双[2-(2-氯化乙氧基)乙基]醚 、 4-氨基苯硫酚 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以74%的产率得到1,11-Bis(4-aminophenylthio)-3,6,9-trioxaundecane
  参考文献：
  名称：

  Self-Assembly of Novel [2]Catenanes and [2]Pseudorotaxanes Incorporating Thiacrown Ethers or Their Acyclic Analogues

  摘要：

  AbstractA series of π electron rich macrocyclic polythioethers and their acyclic analogues have been synthesized in good yields. The association constants for the complexation of the π electron deficient bis(hexafluorophosphate) bipyridinium‐based salt, paraquat, by these macrocycles, as well as those for the complexation of corresponding acyclic compounds by the bipyridinium‐based tetracationic cyclophane, cyclobis(paraquat‐p‐phenylene), are significantly lower than those observed in the case of the “all‐oxygen” analogues. Nonetheless, yields as high as 86% were recorded in the template‐directed syntheses of [2]catenanes composed of cyclobis(paraquat‐p‐phenylene) and the macrocyclic polythioethers. Single‐crystal X‐ray crystallographic analyses of the [2]catenanes incorporating constitutionally unsymmetrical π electron rich macrocyclic polythioethers revealed that, in all cases, the dioxyaromatic units are located inside the cavity of the tetracationic cyclophane component in preference to the dithiaaromatic units. A similar selectivity was observed in solution by variable‐temperature 1H NMR spectroscopy. However, inversion of the ratio between the two translational isomers of the two [2]catenanes bearing 1,5‐dithi‐anaphthalene, as one of their π electron rich ring systems, and either 1,4‐dioxy‐benzene or 1,5‐dioxynaphthalene, as the other, occurs upon increasing the temperature from –30 to +30 πC. These [2]catenanes can be viewed as temperature‐responsive molecular switches.

  DOI：

  10.1002/chem.19970030518