cone-5,11,17,23,29-pentabromo-31,32,33,34,35-pentakis(tert-butoxycarbonylmethoxy)calic[5]arene | 330477-38-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cone-5,11,17,23,29-pentabromo-31,32,33,34,35-pentakis(tert-butoxycarbonylmethoxy)calic[5]arene
• 英文别名: cone-5,11,17,23,29-pentabromo-31,32,33,34,35-pentakis(tert-butoxycarbonylmethoxy)calix[5]arene；Tert-butyl 2-[[5,11,17,23,29-pentabromo-32,33,34,35-tetrakis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]-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]oxy]acetate
• CAS: 330477-38-8
• 化学式: C₆₅H₇₅Br₅O₁₅
• 分子量: 1495.82
• InChiKey: IXLFKXICUVUOBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  85
• 可旋转键数：
  25
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  178
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  4-二乙基吡啶硼烷 、 cone-5,11,17,23,29-pentabromo-31,32,33,34,35-pentakis(tert-butoxycarbonylmethoxy)calic[5]arene 在 四(三苯基膦)钯 、 cesium fluoride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.0h， 以20%的产率得到cone-5,11,17,23,29-penta(4-pyridyl)-31,32,33,34,35-pentakis(tert-butoxycarbonylmethoxy)calix[5]arene
  参考文献：
  名称：

  Metal-Mediated Self-Assembly of Pyridylcalixarenes:  Prevention of Intramolecular Metal Chelation Is Essential in Constructing Molecular Capsules

  摘要：

  To construct calixarene-based molecular capsules utilizing the pyridyl-Pd(II) interaction, reactions of cone-pyridylcalix[4] arene 3, cone-pyridylcalix[5]arene 13, and cone-pyridylcalix[il arene bis-crown 16 with square-planar Pd(II) complex 7 were investigated. Because of the coexistence of intermolecular binding and chelate-forming intramolecular binding, the reactions of cone-pyridylcalix[4]arene 3 or cone-pyridylcalix[5]arene 13 with cis-Pd(II) complex 7 yield complicated, structure-unknown oligomers. The short dioxyethylene bridges on the lower rim of pyridylcalix[4] arene his-crown 16 rigidify the cone conformation and thus prohibit 16 from the intramolecular binding with a metal component. Thus, two cone-tetrapyridylcalix[4] arene his-crown 16 and four cis-Pd(II) complex molecules self-assemble into molecular capsules that exist as a parallel/antiparallel conformer mixture in a nearly 1:1 ratio. The results demonstrated that to prevent entropically favorable intramolecular binding is essential in constructing higher capsule-like structures with calixarene building blocks by self-assembling.

  DOI：

  10.1021/jo0011686
• 作为产物：
  描述：

  杯[5]芳烃 在 溴 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 cone-5,11,17,23,29-pentabromo-31,32,33,34,35-pentakis(tert-butoxycarbonylmethoxy)calic[5]arene
  参考文献：
  名称：

  Metal-Mediated Self-Assembly of Pyridylcalixarenes:  Prevention of Intramolecular Metal Chelation Is Essential in Constructing Molecular Capsules

  摘要：

  To construct calixarene-based molecular capsules utilizing the pyridyl-Pd(II) interaction, reactions of cone-pyridylcalix[4] arene 3, cone-pyridylcalix[5]arene 13, and cone-pyridylcalix[il arene bis-crown 16 with square-planar Pd(II) complex 7 were investigated. Because of the coexistence of intermolecular binding and chelate-forming intramolecular binding, the reactions of cone-pyridylcalix[4]arene 3 or cone-pyridylcalix[5]arene 13 with cis-Pd(II) complex 7 yield complicated, structure-unknown oligomers. The short dioxyethylene bridges on the lower rim of pyridylcalix[4] arene his-crown 16 rigidify the cone conformation and thus prohibit 16 from the intramolecular binding with a metal component. Thus, two cone-tetrapyridylcalix[4] arene his-crown 16 and four cis-Pd(II) complex molecules self-assemble into molecular capsules that exist as a parallel/antiparallel conformer mixture in a nearly 1:1 ratio. The results demonstrated that to prevent entropically favorable intramolecular binding is essential in constructing higher capsule-like structures with calixarene building blocks by self-assembling.

  DOI：

  10.1021/jo0011686

文献信息

• Synthesis of terpyridine-substituted calix[n]arenes
  作者：Junmin Liu、Markus Tonigold、Björn Bredenkötter、Tobias Schröder、Jochen Mattay、Dirk Volkmer

  DOI：10.1016/j.tetlet.2009.01.044

  日期：2009.3

  Calix[n]arenes (n = 4,5) comprising 4-(2,2':6',2 ''-terpyridyl)-phenyl substituents at the upper rim were synthesized for the first time, employing Suzuki-type coupling reactions. All calix[n]arene derivatives were prepared as cone conformers. The single crystal X-ray structure of cone-5,11,17,23-tetra4-(2,2':6',2 ''-terpyridyl)-phenyl)-25,26,27,28-tetrabutoxycalix[4]arene 4 is analyzed in terms Of Structural rigidity and potential use of these ligands as novel synthons of cage-type metallosupramolecular assemblies. (C) 2009 Elsevier Ltd. All rights reserved.
• Metal-Mediated Self-Assembly of Pyridylcalixarenes:  Prevention of Intramolecular Metal Chelation Is Essential in Constructing Molecular Capsules
  作者：Zhenlin Zhong、Atsushi Ikeda、Masatsugu Ayabe、Seiji Shinkai、Shigeru Sakamoto、Kentaro Yamaguchi

  DOI：10.1021/jo0011686

  日期：2001.2.1

  To construct calixarene-based molecular capsules utilizing the pyridyl-Pd(II) interaction, reactions of cone-pyridylcalix[4] arene 3, cone-pyridylcalix[5]arene 13, and cone-pyridylcalix[il arene bis-crown 16 with square-planar Pd(II) complex 7 were investigated. Because of the coexistence of intermolecular binding and chelate-forming intramolecular binding, the reactions of cone-pyridylcalix[4]arene 3 or cone-pyridylcalix[5]arene 13 with cis-Pd(II) complex 7 yield complicated, structure-unknown oligomers. The short dioxyethylene bridges on the lower rim of pyridylcalix[4] arene his-crown 16 rigidify the cone conformation and thus prohibit 16 from the intramolecular binding with a metal component. Thus, two cone-tetrapyridylcalix[4] arene his-crown 16 and four cis-Pd(II) complex molecules self-assemble into molecular capsules that exist as a parallel/antiparallel conformer mixture in a nearly 1:1 ratio. The results demonstrated that to prevent entropically favorable intramolecular binding is essential in constructing higher capsule-like structures with calixarene building blocks by self-assembling.