11,23-diiodo-5,17,29-trimethyl-31,32,33,34,35-pentaacetoxycalix[5]arene | 207981-91-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 11,23-diiodo-5,17,29-trimethyl-31,32,33,34,35-pentaacetoxycalix[5]arene
• 英文别名: (32,33,34,35-Tetraacetyloxy-5,23-diiodo-11,17,29-trimethyl-31-hexacyclo[25.3.1.13,7.19,13.115,19.121,25]pentatriaconta-1(30),3,5,7(35),9,11,13(34),15(33),16,18,21(32),22,24,27(31),28-pentadecaenyl) acetate
• CAS: 207981-91-7
• 化学式: C₄₈H₄₄I₂O₁₀
• 分子量: 1034.68
• InChiKey: JALPLSKWJBFBDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  60
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  11,23-diiodo-5,17,29-trimethyl-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-iodo-17-ethynyl-11,23,29-trimethyl-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
• 作为产物：
  描述：

  乙酸酐 、 5,17-diiodo-11,23,29-trimethyl-31,32,33,34,35-pentahydroxycalix[5]arene 在 吡啶 作用下， 反应 12.0h， 以82%的产率得到11,23-diiodo-5,17,29-trimethyl-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

文献信息

• Synthesis of a calix[5]arene receptor having two benzoic acid moieties
  作者：Takeharu Haino、Koji Nitta、Yoshikazu Saijo、Kazumi Matsumura、Masaki Hirakata、Yoshimasa Fukazawa

  DOI：10.1016/s0040-4039(99)01289-7

  日期：1999.8

  Synthesis and binding behavior of a calix[5]arene receptor possessing two benzoic acids are reported. Two water molecules were bound within the cavity by hydrogen bonding interaction between the two carboxylic acids of the receptor. It also binds 2-aminopyrimidine to form a complex in which the aromatic ring of the guest resides deeply within the cavity. (C) 1999 Elsevier Science Ltd. All rights reserved.