5,11-bis(3'-pyridylazo)-25,26,27,28-tetrahydroxycalix[4]arene | 909107-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,11-bis(3'-pyridylazo)-25,26,27,28-tetrahydroxycalix[4]arene
• CAS: 909107-25-1
• 化学式: C₃₈H₃₀N₆O₄
• 分子量: 634.694
• InChiKey: FOLTUIXGMWNNCL-CHQNLTHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.81
• 重原子数：
  48.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  156.14
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5,11-bis(3'-pyridylazo)-25,26,27,28-tetrahydroxycalix[4]arene 、 4-氨基吡啶 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以58%的产率得到5,11-bis(3'-pyridylazo)-17-(4'-pyridylazo)-25,26,27,28-tetrahydroxycalix[4]arene
  参考文献：
  名称：

  Synthesis of cesium selective pyridyl azocalix[n]arenes

  摘要：

  A series of pyridylazo calix[n]arenes (n=4, 6, 8) including the first examples of mixed hetroaryl azocalix(n)arene, have been synthesized by coupling calix[n]arenes with diazonium salts derived from amino pyridines. It has been observed that the coupling reaction of diazonium salt obtained from 3-aminopyridine with calix[n]arene gives tetrakis-, hexakis- and octakis (pyridylazo)calix[n]arenes (n=4,6 8) while those derived front 4-aminopyridine give partially substituted (4-pyridylazo)calix[n]arene analogs. There is no reaction of calix(n)arenes with diazonium salts derived from 2-aminopyridine under identical conditions of experiments. The conformational analysis of synthesized compounds have been ascertained by detailed spectral measurements and single crystal X-ray analysis of 5-(3'-pyridylazo)-25,26,27,28-tetrahydroxycalix[4]arene. A rational explanation for the observed partial and exhaustive coupling reaction in the synthesis of heteroaryl azocalix(n)arenes has been suggested. Preliminary evaluation of synthesized derivatives as molecular receptors for metal ions indicates that they have good potential to function as selective ionic filters for cesium ions. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.01.022
• 作为产物：
  描述：

  3-氨基吡啶 、 杯[4]芳烃 在 盐酸 、 sodium nitrite 、 sodium acetate 作用下， 以 水 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 以35%的产率得到5,11-bis(3'-pyridylazo)-25,26,27,28-tetrahydroxycalix[4]arene
  参考文献：
  名称：

  Synthesis of cesium selective pyridyl azocalix[n]arenes

  摘要：

  A series of pyridylazo calix[n]arenes (n=4, 6, 8) including the first examples of mixed hetroaryl azocalix(n)arene, have been synthesized by coupling calix[n]arenes with diazonium salts derived from amino pyridines. It has been observed that the coupling reaction of diazonium salt obtained from 3-aminopyridine with calix[n]arene gives tetrakis-, hexakis- and octakis (pyridylazo)calix[n]arenes (n=4,6 8) while those derived front 4-aminopyridine give partially substituted (4-pyridylazo)calix[n]arene analogs. There is no reaction of calix(n)arenes with diazonium salts derived from 2-aminopyridine under identical conditions of experiments. The conformational analysis of synthesized compounds have been ascertained by detailed spectral measurements and single crystal X-ray analysis of 5-(3'-pyridylazo)-25,26,27,28-tetrahydroxycalix[4]arene. A rational explanation for the observed partial and exhaustive coupling reaction in the synthesis of heteroaryl azocalix(n)arenes has been suggested. Preliminary evaluation of synthesized derivatives as molecular receptors for metal ions indicates that they have good potential to function as selective ionic filters for cesium ions. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.01.022

文献信息

• Shaping the cavity of calixarene architecture for molecular recognition: synthesis and conformational properties of new azocalix[4]arenes
  作者：Har Mohindra Chawla、Suneel Pratap Singh、Satya Narayan Sahu、Shailesh Upreti

  DOI：10.1016/j.tet.2006.05.040

  日期：2006.8

  A series of new azocalix[4]arenes containing one, two, three, and four free phenolic groups have been synthesized through the reaction of 4-nitro- and 2,4-dinitrophenylhydrazines with flexible calix[4]arene diquinones as well as through diazocoupling reactions of calix[4]arenes. Characterization of synthesized compounds by spectroscopic methods and X-ray diffraction revealed that azocalix[4]arenes

  通过4-硝基-和2,4-二硝基苯肼与柔性杯[4]芳烃二醌的反应以及通过4-硝基-和2,4-二硝基苯肼的合成，合成了一系列含有一个，两个，三个和四个游离酚基的新型偶氮杯[4]芳烃。杯[4]芳烃的重氮偶合反应。通过光谱方法和X射线衍射表征合成的化合物表明，如果azocalix [4]芳烃包含至少一个游离酚基，则它们呈圆锥构象。偶氮杯[4]芳烃的部分锥形或1,3-交替构象只有在没有游离酚基的情况下才能产生。结果可用于塑造杯[4]芳烃体系，以实现离子和分子识别。