5,17-bis(o-methoxyphenyl)azo-25,27-bis(1-benzyl-1H-1,2,3-triazolylmethyloxy)-26,28-dipropyloxycalix[4]arene

• 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: 5,17-bis(o-methoxyphenyl)azo-25,27-bis(1-benzyl-1H-1,2,3-triazolylmethyloxy)-26,28-dipropyloxycalix[4]arene
• 英文别名: [25,27-Bis[(1-benzyltriazol-4-yl)methoxy]-17-[(2-methoxyphenyl)diazenyl]-26,28-dipropoxy-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaenyl]-(2-methoxyphenyl)diazene；[25,27-bis[(1-benzyltriazol-4-yl)methoxy]-17-[(2-methoxyphenyl)diazenyl]-26,28-dipropoxy-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaenyl]-(2-methoxyphenyl)diazene
• 化学式: C₆₈H₆₆N₁₀O₆
• 分子量: 1119.34
• InChiKey: GQTSSIYDESSMEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  84
• 可旋转键数：
  22
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  25,27-dipropargyloxy-26,28-dihydroxy-calix[4]arene 在 盐酸 、 copper(l) iodide 、 sodium hydride 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 111.0h， 生成 5,17-bis(o-methoxyphenyl)azo-25,27-bis(1-benzyl-1H-1,2,3-triazolylmethyloxy)-26,28-dipropyloxycalix[4]arene
  参考文献：
  名称：

  A specific and ratiometric chemosensor for Hg2+ based on triazole coupled ortho-methoxyphenylazocalix[4]arene

  摘要：

  Calix[4]arene 3, which contains two distal triazole groups on the lower rim and two distal o-methoxyphenylazo groups on the upper rim, was synthesized and found to be a specific and ratiometric sensor for Hg2+ in a polar protic solvent. A series of o-methoxyphenylazo derivatives (3, 4, 5, 7, and 9) were synthesized, which proved that the lower-rim triazoles and the hydroxyl azophenol(s) were the major ligands for metal ion binding. Though analogues 4 and 10 showed some sensitivity for Hg2+, compound 3 was the only ratiometric chemosensor for Hg2+ among the series of azocalix[4]arenes synthesized in this work. The formation of 3. Hg2+ complex was supported by UV/vis and NMR titration studies and Mass spectrometry. Based on the symmetrical features of NMR spectra of 3 center dot Hg2+, the complex is believed to be symmetrical with respect to the calix[4]arene cavity. Furthermore, the complex was determined to be 1:1 binding stoichiometry by Job's plot, and the association constant was determined to be 4.02 x 10(3) M-1 using Benesi-Hildebrand plot. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.052

文献信息

• A specific and ratiometric chemosensor for Hg2+ based on triazole coupled ortho-methoxyphenylazocalix[4]arene
  作者：Nae-Jen Wang、Chung-Ming Sun、Wen-Sheng Chung

  DOI：10.1016/j.tet.2011.08.052

  日期：2011.10

  Calix[4]arene 3, which contains two distal triazole groups on the lower rim and two distal o-methoxyphenylazo groups on the upper rim, was synthesized and found to be a specific and ratiometric sensor for Hg2+ in a polar protic solvent. A series of o-methoxyphenylazo derivatives (3, 4, 5, 7, and 9) were synthesized, which proved that the lower-rim triazoles and the hydroxyl azophenol(s) were the major ligands for metal ion binding. Though analogues 4 and 10 showed some sensitivity for Hg2+, compound 3 was the only ratiometric chemosensor for Hg2+ among the series of azocalix[4]arenes synthesized in this work. The formation of 3. Hg2+ complex was supported by UV/vis and NMR titration studies and Mass spectrometry. Based on the symmetrical features of NMR spectra of 3 center dot Hg2+, the complex is believed to be symmetrical with respect to the calix[4]arene cavity. Furthermore, the complex was determined to be 1:1 binding stoichiometry by Job's plot, and the association constant was determined to be 4.02 x 10(3) M-1 using Benesi-Hildebrand plot. (C) 2011 Elsevier Ltd. All rights reserved.