rccc-5,17-bis(hydroxymethyl)-11,23-bis[methoxycarbonyl]-4,6,10,12,16,18,22,24-octa-O-methyl-2,8,14,20-tetra(n-undecyl)resorc[4]arene | 762272-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: rccc-5,17-bis(hydroxymethyl)-11,23-bis[methoxycarbonyl]-4,6,10,12,16,18,22,24-octa-O-methyl-2,8,14,20-tetra(n-undecyl)resorc[4]arene
• CAS: 762272-76-4
• 化学式: C₈₂H₁₃₂O₁₀
• 分子量: 1277.94
• InChiKey: UZGLGHSIBNGSNF-ZKAWCBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.26
• 重原子数：
  92.0
• 可旋转键数：
  50.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114.3
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  rccc-5,17-bis(hydroxymethyl)-11,23-bis[methoxycarbonyl]-4,6,10,12,16,18,22,24-octa-O-methyl-2,8,14,20-tetra(n-undecyl)resorc[4]arene 在 三溴化磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到rccc-5,17-bis(bromomethyl)-11,23-bis[methoxycarbonyl]-4,6,10,12,16,18,22,24-octa-O-methyl-2,8,14,20-tetra(n-undecyl)resorc[4]arene
  参考文献：
  名称：

  Kemp's triacid attached to octa-O-methyl resorc[4]arenes: conformations in solution and comparative binding studies with various 2-amino pyridines

  摘要：

  We synthesized the new supramolecular host molecules 7 and 13 based on functionalized resorcarenes bearing Kemp's triacid. Conformations in solution have been investigated and the influence of intra-and intermolecular hydrogen bonds from the triacid was shown by low temperature and DOSY NMR experiments. The results of host 7 are supported by DFT calculations. The binding behaviour of 7 towards different 2-amino pyridincs in chloroform has been investigated by NMR titrations. The association constants reach from K 207 M-1 for 2-amino-5-cyano pyridine to K=1551 M-1 for 2-amino-4-methyl pyridine. The association constants of the formed complexes of 7 with 2-amino pyridines were compared with those of the simple host systems 14 and 15 in order to evaluate the influence of the attached resorcarene host. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.138
• 作为产物：
  描述：

  rccc-5,17-dibromo-11,23-bis[methoxycarbonyl]-4,6,10,12,16,18,22,24-octa-O-methyl-2,8,14,20-tetra(n-undecyl)resorc[4]arene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 以88%的产率得到rccc-5,17-bis(hydroxymethyl)-11,23-bis[methoxycarbonyl]-4,6,10,12,16,18,22,24-octa-O-methyl-2,8,14,20-tetra(n-undecyl)resorc[4]arene
  参考文献：
  名称：

  Kemp's triacid attached to octa-O-methyl resorc[4]arenes: conformations in solution and comparative binding studies with various 2-amino pyridines

  摘要：

  We synthesized the new supramolecular host molecules 7 and 13 based on functionalized resorcarenes bearing Kemp's triacid. Conformations in solution have been investigated and the influence of intra-and intermolecular hydrogen bonds from the triacid was shown by low temperature and DOSY NMR experiments. The results of host 7 are supported by DFT calculations. The binding behaviour of 7 towards different 2-amino pyridincs in chloroform has been investigated by NMR titrations. The association constants reach from K 207 M-1 for 2-amino-5-cyano pyridine to K=1551 M-1 for 2-amino-4-methyl pyridine. The association constants of the formed complexes of 7 with 2-amino pyridines were compared with those of the simple host systems 14 and 15 in order to evaluate the influence of the attached resorcarene host. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.138