25,26,27,28-tetrakis(methoxyethoxy)-5,11,17,23-tetrakis(cyano)calix[4]arene | 219322-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25,26,27,28-tetrakis(methoxyethoxy)-5,11,17,23-tetrakis(cyano)calix[4]arene
• 英文别名: 25,26,27,28-Tetrakis(2-methoxyethoxy)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-5,11,17,23-tetracarbonitrile
• CAS: 219322-76-6
• 化学式: C₄₄H₄₄N₄O₈
• 分子量: 756.855
• InChiKey: HXCPOPJQXUKIML-UHFFFAOYSA-N

物化性质

• 沸点：
  945.0±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  25,26,27,28-tetrakis(methoxyethoxy)-5,11,17,23-tetrakis(cyano)calix[4]arene 在 sodium azide 、 zinc dibromide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以65%的产率得到5-[25,26,27,28-tetrakis(2-methoxyethoxy)-11,17,23-tris(2H-tetrazol-5-yl)-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]-2H-tetrazole
  参考文献：
  名称：

  Recognition Properties of Carboxylic Acid Bioisosteres: Anion Binding by Tetrazoles, Aryl Sulfonamides, and Acyl Sulfonamides on a Calix[4]arene Scaffold

  摘要：

  Tetrazoles and acyl sulfonamides are functional groups that are common in medicinal chemistry but virtually unexplored as recognition elements in supramolecular chemistry. We report here on the anion binding properties of these highly acidic N-H functional groups. We have prepared two new calixarene-based tetrazole-containing hosts, as well as new acetyl sulfonamide and benzoyl sulfonamide hosts. We also report on analogous hosts bearing the better-known aryl sulfonamide functional group as a point of comparison. We find that these hosts are competent anion binders and that the recognition of anions by these groups is highly dependent on their conformational preferences. We also report in detail on the preferred molecular shape of each acid bioisostere as determined by calculations and structural database surveys, and discuss how these shapes impact binding in the context of the reported hosts.

  DOI：

  10.1021/jo200031u
• 作为产物：
  描述：

  25,26,27,28-tetrakis(methoxyethoxy)calix[4]arene 在 N-甲基吡咯烷酮 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 丁酮 为溶剂， 生成 25,26,27,28-tetrakis(methoxyethoxy)-5,11,17,23-tetrakis(cyano)calix[4]arene
  参考文献：
  名称：

  Synthesis and structural analysis of an infinite linear coordination network formed by the self-assembly of tetracyanocalix[4]arene ligands and silver cations

  摘要：

  利用杯[4]芳烃下缘的O-烷基化来强加1,3-交替构象，并利用上缘的官能化来建立四个以不同方式指向的腈基团，从而形成一种外配体获得了形成线性配位网络的方法；后者与银阳离子自组装后，获得了线性配位聚合物，并通过 X 射线研究进行了固态结构分析。

  DOI：

  10.1039/a807434h