5,11,17,23-tetraamino-25,26,27,28-tetraethoxyethoxycalix[4]arene | 170172-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23-tetraamino-25,26,27,28-tetraethoxyethoxycalix[4]arene
• 英文别名: 25,26,27,28-Tetrakis(2-ethoxyethoxy)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-tetramine；25,26,27,28-tetrakis(2-ethoxyethoxy)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-tetramine
• CAS: 170172-09-5
• 化学式: C₄₄H₆₀N₄O₈
• 分子量: 772.982
• InChiKey: HUNAKNPAFCNPPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  56
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  178
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  胆酸 、 5,11,17,23-tetraamino-25,26,27,28-tetraethoxyethoxycalix[4]arene 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以70%的产率得到
  参考文献：
  名称：

  Environmentally Responsive Molecular Baskets:  Unimolecular Mimics of Both Micelles and Reversed Micelles

  摘要：

  When four facially amphiphilic cholate derivatives are attached to a tetraaminocalixarene scaffold, the resulting molecule responds to environmental changes by rotation of the cholate units. In polar solvents, the molecule adopts a micellelike conformation with the hydrophilic alpha-faces of the cholates pointing outward. In nonpolar solvents, it turns inside out, assuming a reversed micellelike conformation with the hydrophobic beta-faces pointing outward. Switching between the two conformations is driven by solvophobic interactions and is fully reversible.

  DOI：

  10.1021/ol048679p
• 作为产物：
  描述：

  25,26,27,28-Tetrakis(ethoxyethoxy)-5,11,17,23-tetranitrocalix<4>arene 在 镍 一水合肼 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以79%的产率得到5,11,17,23-tetraamino-25,26,27,28-tetraethoxyethoxycalix[4]arene
  参考文献：
  名称：

  Yang, Xiaoguang; McBranch, Duncan; Swanson, Basil, Angewandte Chemie, 1996, vol. 108, # 5, p. 572 - 575

  摘要：

  DOI：

文献信息

• A Structure‐Activity Investigation on Modified Analogues of an Argininocalixarene Based Non‐viral Gene Vector
  作者：Michela Lomazzi、Valentina Franceschi、Valentina Bagnacani、Carlo Alberto Vezzoni、Gaetano Donofrio、Alessandro Casnati、Francesco Sansone

  DOI：10.1002/ejoc.202100338

  日期：2021.8.6

  alkyl chains at the lower rim were synthesized and studied in pDNA binding and cell transfection in order to dissect the role of each of these structural elements on gene delivery properties of this promising class of non-viral vectors.

  合成了一系列八种新型杯[4]芳烃-锥体两亲物，它们在上缘具有不同类型和数量的阳离子头基，在下缘具有不同的烷基链，并研究了在 pDNA 结合和细胞转染中的作用。这些结构元件中的每一个都与这种有前途的非病毒载体的基因传递特性有关。
• Scheerder, Jurgen; Duynhoven, John P. M. van; Engbersen, Johan F. J., Angewandte Chemie, 1996, vol. 108, # 10, p. 1172 - 1175
  作者：Scheerder, Jurgen、Duynhoven, John P. M. van、Engbersen, Johan F. J.、Reinhoudt, David N.

  DOI：——

  日期：——
• A C-linked peptidocalix[4]arene bearing four dansyl groups: a highly selective fluorescence chemosensor for fluoride ions
  作者：Ru Miao、Qi-Yu Zheng、Chuan-Feng Chen、Zhi-Tang Huang

  DOI：10.1016/j.tetlet.2004.04.137

  日期：2004.6

  A new C-linked peptidocalix[4]arene functionalized with four L-alanine and dansyl units at the upper rim has been prepared, which exhibited highly selective recognition towards F- along with weaker complexation to AcO- and H2PO4- and no complexation to Cl-, Br-, P-, and HSO4- by fluorescence spectroscopy and H-1 NMR method. (C) 2004 Elsevier Ltd. All rights reserved.
• Upper Rim Guanidinocalix[4]arenes as Artificial Phosphodiesterases
  作者：Laura Baldini、Roberta Cacciapaglia、Alessandro Casnati、Luigi Mandolini、Riccardo Salvio、Francesco Sansone、Rocco Ungaro

  DOI：10.1021/jo300193y

  日期：2012.4.6

  Calix[4]arene derivatives, blocked in the cone conformation and functionalized with two to four guanidinium units at the upper rim were synthesized and investigated as catalysts in the cleavage of the RNA model compound 2-hydroxypropyl p-nitrophenyl phosphate. When compared with the behavior of a monofunctional model compound, the catalytic superiority of the calix[4]arene derivatives points to a high level of cooperation between catalytic groups. Combination of acidity measurements with the pH dependence of catalytic rates unequivocally shows that a necessary requisite for effective catalysis is the simultaneous presence, on the same molecular framework, of a neutral guanidine acting as a general base and a protonated guanidine acting as an electrophilic activator. The additional guanidinium (guanidine) group in the diprotonated (monoprotonated) trifunctional calix[4]arene acts as a more or less innocent spectator. This is not the case with the tetrasubstituted calix[4]arene, whose mono-, di-, and triprotonated forms are slightly less effective than the corresponding di- and triguanidinocalix[4]arene derivatives, most likely on account of a steric interference with HPNP caused by overcrowding.
• Environmentally Responsive Molecular Baskets:  Unimolecular Mimics of Both Micelles and Reversed Micelles
  作者：Eui-Hyun Ryu、Yan Zhao

  DOI：10.1021/ol048679p

  日期：2004.9.1

  When four facially amphiphilic cholate derivatives are attached to a tetraaminocalixarene scaffold, the resulting molecule responds to environmental changes by rotation of the cholate units. In polar solvents, the molecule adopts a micellelike conformation with the hydrophilic alpha-faces of the cholates pointing outward. In nonpolar solvents, it turns inside out, assuming a reversed micellelike conformation with the hydrophobic beta-faces pointing outward. Switching between the two conformations is driven by solvophobic interactions and is fully reversible.