5-ethynyl-11,17,23,29-tetramethyl-31,32,33,34,35-pentaacetoxycalix[5]arene | 878998-11-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 5-ethynyl-11,17,23,29-tetramethyl-31,32,33,34,35-pentaacetoxycalix[5]arene
• CAS: 878998-11-9
• 化学式: C₅₁H₄₈O₁₀
• 分子量: 820.936
• InChiKey: WBMUQSKZYIKEJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  61.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  131.5
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5-ethynyl-11,17,23,29-tetramethyl-31,32,33,34,35-pentaacetoxycalix[5]arene 在 吡啶 、 copper diacetate 作用下， 反应 3.0h， 以0.28 g的产率得到
  参考文献：
  名称：

  Fullerene encapsulation with calix[5]arenes

  摘要：

  This paper presents the synthesis of the fullerene hosts based on the calix[5]arenes and their binding properties. Calix[5]arenes la, 2, 3a bind C-60 or C-70 in organic solvents. The solvent effect of the fullerene complexation was clearly observed; the association constant decreases in a solvent with high solubility for C-60. Covalently linked double-calix[5]arenes 4-6 were also investigated on their binding properties for fullerenes in organic solvents. Their binding abilities for both C-60 and C-70 are extremely high in toluene solution. Higher binding selectivity toward C-70 is observed by all the double-calix[5]arenes. The selectivity of 5a toward C-70/C-60 is highest in toluene with a value of 10. The structures of the supramolecular complexes of the calix[5]arene hosts and C-60 or C-70 were investigated by using H-1 and C-13 NMR studies. The molecular mechanics calculation and X-ray structure reveal that the interior of the calix[5]arene is complementary to the exterior Of C-60 molecule. In contrast, the host-guest complexes Of C-70 With the simple calix[5]arenes take many conformational options due to its less symmetric shape. The molecular mechanics calculation and our chemical shift simulation nicely worked to estimate the reliable structures; the calix[5]arene cavity takes up C-70 molecule, and the C-70 molecule tilts significantly from the C5 axis of the calix[5]arene. In the case of the host-guest complex Of C-70 with the double-calix[5]arene, the molecular dynamics simulation of the host-guest complex represented the realistic movement of the bound C-70 inside the cavity. The combination of the molecular dynamics simulation and the chemical shift simulation of the host-guest complex suggested that the C-70 molecule rapidly moves inside the cavity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.121
• 作为产物：
  描述：

  5-iodo-11,17,23,29-tetramethyl-31,32,33,34,35-pentaacetoxycalix[5]arene 在 四(三苯基膦)钯 potassium fluoride 、 copper(l) iodide 、 正丁胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 5-ethynyl-11,17,23,29-tetramethyl-31,32,33,34,35-pentaacetoxycalix[5]arene
  参考文献：
  名称：

  Fullerene encapsulation with calix[5]arenes

  摘要：

  This paper presents the synthesis of the fullerene hosts based on the calix[5]arenes and their binding properties. Calix[5]arenes la, 2, 3a bind C-60 or C-70 in organic solvents. The solvent effect of the fullerene complexation was clearly observed; the association constant decreases in a solvent with high solubility for C-60. Covalently linked double-calix[5]arenes 4-6 were also investigated on their binding properties for fullerenes in organic solvents. Their binding abilities for both C-60 and C-70 are extremely high in toluene solution. Higher binding selectivity toward C-70 is observed by all the double-calix[5]arenes. The selectivity of 5a toward C-70/C-60 is highest in toluene with a value of 10. The structures of the supramolecular complexes of the calix[5]arene hosts and C-60 or C-70 were investigated by using H-1 and C-13 NMR studies. The molecular mechanics calculation and X-ray structure reveal that the interior of the calix[5]arene is complementary to the exterior Of C-60 molecule. In contrast, the host-guest complexes Of C-70 With the simple calix[5]arenes take many conformational options due to its less symmetric shape. The molecular mechanics calculation and our chemical shift simulation nicely worked to estimate the reliable structures; the calix[5]arene cavity takes up C-70 molecule, and the C-70 molecule tilts significantly from the C5 axis of the calix[5]arene. In the case of the host-guest complex Of C-70 with the double-calix[5]arene, the molecular dynamics simulation of the host-guest complex represented the realistic movement of the bound C-70 inside the cavity. The combination of the molecular dynamics simulation and the chemical shift simulation of the host-guest complex suggested that the C-70 molecule rapidly moves inside the cavity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.121