25,26,27,28-tetrakis(methoxyethoxy)calix[4]arene | 143433-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25,26,27,28-tetrakis(methoxyethoxy)calix[4]arene
• 英文别名: tetrakis(methoxyethoxy)calix[4]arene；25,26,27,28-Tetrakis(2-methoxyethoxy)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene
• CAS: 143433-58-3
• 化学式: C₄₀H₄₈O₈
• 分子量: 656.816
• InChiKey: TUCJJVZRLBMEED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  25,26,27,28-tetrakis(methoxyethoxy)calix[4]arene 在 N-甲基吡咯烷酮 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 丁酮 为溶剂， 生成 25,26,27,28-tetrakis(methoxyethoxy)-5,11,17,23-tetrakis(cyano)calix[4]arene
  参考文献：
  名称：

  Synthesis and structural analysis of an infinite linear coordination network formed by the self-assembly of tetracyanocalix[4]arene ligands and silver cations

  摘要：

  利用杯[4]芳烃下缘的O-烷基化来强加1,3-交替构象，并利用上缘的官能化来建立四个以不同方式指向的腈基团，从而形成一种外配体获得了形成线性配位网络的方法；后者与银阳离子自组装后，获得了线性配位聚合物，并通过 X 射线研究进行了固态结构分析。

  DOI：

  10.1039/a807434h
• 作为产物：
  描述：

  杯[4]芳烃 在 potassium carbonate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 25,26,27,28-tetrakis(methoxyethoxy)calix[4]arene
  参考文献：
  名称：

  Tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation

  摘要：

  A general method has been developed for the preparation f tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation (3a,c-e) starting from p-tert-butylcalix[4]arenes 1a,b using Cs2CO3 in DMF. The 1,3-alternate conformation was unequivocally proved by an X-ray structure determination of 3a. The scope of the reaction was investigated starting from a series of diametrically di-O-alkylated calix[4]arenes 4a-e having different substituents R2 (t-Bu, CHO, NO2, Br, CN) at the para positions of the phenolic rings. The reactions of 4a-d (R2 = t-Bu, CHO, NO2, Br) yielded the corresponding tetra-0-alkylated calix[4]arenes in the 1,3-alternate conformation 5a-d (51-73%). However, the dicyanocalix[4]arene 4e gave the partial cone conformer 6 as the major reaction product.

  DOI：

  10.1021/jo00046a021

文献信息

• Structure–activity studies on a library of potent calix[4]arene-based PDGF antagonists that inhibit PDGF-stimulated PDGFR tyrosine phosphorylation
  作者：Huchen Zhou、De-an Wang、Laura Baldini、Eileen Ennis、Rishi Jain、Adam Carie、Saïd M. Sebti、Andrew D. Hamilton

  DOI：10.1039/b515483a

  日期：——

  Platelet-derived growth factor (PDGF) and its receptor PDGFR are required for tumor growth and angiogenesis, so disruption of the PDGF–PDGFR interaction should lead to starvation of tumors and reduction of tumor growth. Potent PDGF antagonists have been discovered through the synthesis of a series of calix[4]arene-based compounds that are designed to bind to the three-loop region of PDGF. The effect of lower-rim alkylation, linker and number of interacting head groups on the calix[4]arene scaffold on PDGF affinity and cellular activity has been investigated.

  血小板衍生生长因子（PDGF）及其受体PDGFR对于肿瘤生长和血管生成是必需的，因此，破坏PDGF与PDGFR的相互作用应能导致肿瘤饥饿并减少肿瘤生长。通过合成一系列设计为结合PDGF三环区域的基于calix[4]arene的化合物，发现了强效的PDGF拮抗剂。研究了下缘烷基化、连接剂和相互作用头基数量对calix[4]arene骨架在PDGF亲和力和细胞活性上的影响。
• Exchange Coupling Mediated Through-Bonds and Through-Space in Conformationally Constrained Polyradical Scaffolds:  Calix[4]arene Nitroxide Tetraradicals and Diradical
  作者：Andrzej Rajca、Sumit Mukherjee、Maren Pink、Suchada Rajca

  DOI：10.1021/ja063567+

  日期：2006.10.1

  diagonal nitroxide radicals at the conformationally constrained N...N distance of 5-6 A. Magnetic studies of the calix[4]arene polyradical scaffolds in frozen solutions show that the through-bond exchange coupling in the 1,3-alternate calix[4]arene tetraradical is antiferromagnetic, while that in cone calix[4]arene tetraradical is ferromagnetic. The through-space exchange couplings are antiferromagnetic

  杯[4]芳烃被限制为1,3-交替构象并在上缘用四个和两个叔丁基硝基氧化物功能化，并通过X射线晶体学、磁共振（EPR和（1）H NMR）光谱学表征，和磁性研究。1,3-交替氮氧四自由基和双自由基提供了独特的多自由基支架，用于解剖通过键和通过空间的分子内交换偶联。此外，对先前报道的杯[4]芳烃氮氧四自由基的详细磁性研究，在溶液中具有锥形构象，揭示了交换耦合的构象依赖性。相邻氮氧自由基之间的键合偶联由氮氧-间-亚苯基-CH(2)-间-亚苯基-硝基氧偶联途径介导，在 5-6 A 的构象约束 N...N 距离处发现对角氮氧自由基之间的空间耦合。 冰冻溶液中杯 [4] 芳烃多自由基支架的磁学研究表明，通过键交换耦合在1,3-交替杯中[4]芳烃四价是反铁磁性的，而在锥形杯中[4]芳烃四价是铁磁性的。通过空间交换耦合在锥体和 1,3-交替杯[4]芳烃四价基以及 1,3-交替杯[4]芳烃双价基中都是反铁磁性的。交换耦合常数
• A highly efficient and selective turn-on fluorescent sensor for Cu2+ ion based on calix[4]arene bearing four iminoquinoline subunits on the upper rim
  作者：Guang-Ke Li、Zhen-Xiang Xu、Chuan-Feng Chen、Zhi-Tang Huang

  DOI：10.1039/b800258d

  日期：——

  A new fluorescent chemosensor based on calix[4]arene bearing four iminoquinoline subunits on the upper rim was conveniently synthesized, which showed a remarkable enhanced fluorescent intensity in the presence of Cu(2+) ion and a high selectivity toward Cu(2+) ion over a wide range of tested metal ions in acetonitrile.

  方便地合成了一种基于杯形[4]亚芳基的新型荧光化学传感器，该传感器在上缘带有四个亚氨基喹啉亚基，在存在Cu（2+）离子时，荧光强度显着增强，并且对Cu（2+）的选择性高。乙腈中的各种测试金属离子中的离子。
• Synthesis of and amine recognition with a Cu(II)-bridged biscalix[4]arene
  作者：Kiyoshi Fujimoto、Seiji Shinkai

  DOI：10.1016/s0040-4039(00)76659-7

  日期：1994.5

  A biscalix[4]arene (7) in which the upper rims are linked by two Cu(II)-chelate complexes has been synthesized. This is a novel method for the synthesis of biscalix[4]arenes using the self-association nature of metal ligands. Compound 7 recognized diamine substrates using a cavity composed of two Cu(II)-chelate complexes.
• Chlorosulfonylated calix[4]arenes: precursors for neutral anion receptors with a selectivity for hydrogen sulfate
  作者：Yury Morzherin、Dmitry M. Rudkevich、Willem Verboom、David N. Reinhoudt

  DOI：10.1021/jo00078a052

  日期：1993.12