25,27-bis(5-chloro-3-oxapentyloxy)calix[4]arene | 286460-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25,27-bis(5-chloro-3-oxapentyloxy)calix[4]arene
• 英文别名: 26,28-bis[2-(2-chloroethoxy)ethoxy]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-25,27-diol
• CAS: 286460-88-6
• 化学式: C₃₆H₃₈Cl₂O₆
• 分子量: 637.6
• InChiKey: NPLBJGQKOFQMTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  25,27-bis(5-chloro-3-oxapentyloxy)calix[4]arene 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 25,27-(6-tosyl-3,9-dioxa-6-azaundecane-1,11-diyldioxy)-26,28-(3,6,9-trioxaundecane-1,11-diyldioxy)calix[4]arene
  参考文献：
  名称：

  Two novel 1,3-calix[4]azacrowns

  摘要：

  Two 1,3-calix[4]azacrowns-5 in the 1,3-alternate conformation have been constructed from calix[4]arene. They formed 1:1 endo and 1:2 endo-endo complexes with NH4+ in CDCl3. Comparison with 1,3-calix[4]-bis-crown-5 lead us to conclude a better binding by replacement of the central O atom by NH group in the crown. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00382-8
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 25,27-bis(5-chloro-3-oxapentyloxy)calix[4]arene
  参考文献：
  名称：

  Synthesis, crystal structures and competitive binding property of a family of calix[4]arene-biscrown-5/6 and their application in extraction of alkali metal ions from sea bittern

  摘要：

  A family of calix[4]arene compounds containing crown moieties at both the upper and lower rims of the calix unit with different substituents attached to the nitrogen atom of the aza-crown moiety have been synthesized, characterized and their competitive binding property towards Li+, Na+, Mg2+, Ca2+ and Sr2+ in aqueous media has been investigated. These ionophores exhibit high selectivity towards K+, assessed by two-phase extraction method followed by ion chromatographic assay of the metal ions in the extract. Isothermal calorimetric titration for complex formation with K+ was carried out to evaluate stoichiometry, binding constant and other thermodynamic parameters (Delta H, Delta S and Delta G). For structural elucidation in solution, detail H-1 NMR study was carried out and K+ complexes were isolated for solid state characterization. Molecular structures of two of the ionophores and K+-complex of one of the ionophores has been established by single crystal X-ray study. H-1 NMR, ITC and single crystal XRD studies suggest 1:1 complex formation with encapsulation of K+ in the crown-6 ring at the upper rim. These ionophores have been applied for extraction of metal ions from bittern. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.07.001

文献信息

• Calix[4]arene based fluorescent chemosensor bearing coumarin as fluorogenic unit: Synthesis, characterization, ion-binding property and molecular modeling
  作者：Subrata Patra、Rabindranath Lo、Ashish Chakraborty、Ravi Gunupuru、Debdeep Maity、Bishwajit Ganguly、Parimal Paul

  DOI：10.1016/j.poly.2012.12.002

  日期：2013.2

  A series of calix[4]arene-based fluorescent chemosensors in cone and 1,3-alternate conformations have been synthesised incorporating ethylene glycol units as binding sites and coumarin as fluorescent probe. These compounds have been designed with variation in substituents, conformations of the calixarene unit and steric crowding. The open chain ethylene glycol moieties are flexible so that they can

  已经合成了一系列圆锥形和1,3-交替构型的基于杯[4]芳烃的荧光化学传感器，结合了乙二醇单元作为结合位点和香豆素作为荧光探针。这些化合物经设计具有不同的取代基，杯芳烃单元的构象和空间拥挤。开链乙二醇部分是柔性的，因此它们可以在空间中定向以与金属离子有效地相互作用。这些氟离子载体的离子结合研究已使用大量金属离子进行，离子识别事件通过荧光和吸收光谱法进行监测。在Fe 3+和Cu 2+存在下，发射强度发生大幅度淬灭，而在Ca存在下，发射强度增强2+表明这些金属离子与离​​子载体牢固结合。这些金属离子的络合作用还可以从UV-Vis光谱变化中看出。通过ESMS分析已确认形成的复合物的组成（1∶1）。从荧光滴定数据已经评估了与强相互作用金属离子的结合常数。已经进行了DFT计算，以发现杯状离子载体的金属结合位点，并且在这些情况下，前沿分子轨道分析已使与金属离子络合时观察到的荧光行为合理化。
• Synthesis and characterization of porphyrazines as novel extractants for the removal of Ag(I) and Hg(II) from aqueous solution
  作者：Nilgün Kabay、Yasemin Baygu、H. Korkmaz Alpoguz、Ahmet Kaya、Yaşar Gök

  DOI：10.1016/j.dyepig.2012.09.002

  日期：2013.2

  In this study, the synthesis and characterization of new metal-free and metallo-porphyrazines, peripherally and symmetrically derived from 1,3-alternate26,28-[34,37-dithia-29,32,40,43-tetraoxa-35-en]calix [4]arene-25,27-diol, were performed. Dicyano compound was prepared starting from cis-1,2-dicyano-12-ethylenedithiolate disodium salt and 1,3-alternate 26,28-bis[2-(2-iodoethoxy)ethoxy]calix[4]arene-25,27-diol, which was prepared by the conversion reaction of 26,28-bis[2-(2-chloroethoxy)ethoxy] calix [4]arene-25,27-diol with Nal. The demetalation of magnesium porphyrazine was achieved by the treatment with trifluoroacetic acid that resulted in the metal-free derivative. The solvent extraction of heavy metal cations such as Ag(I), Hg(II), Cu(II), Mn(II), Cr(III), Ni(II), Pb(II) and Zn(II) by the dicyano compounds and its derived metal-free and magnesium porphyrazines was investigated. From the results of two phase extraction studies on the novel compounds, one can conclude that the metal-free and metallo-porphyrazines show very high selectivity for silver and mercury ions when compared with other metal ions. The novel compounds were characterized using the techniques of UV-vis, H-1, C-13 NMR, IR, MS and elemental analysis. (C) 2012 Elsevier Ltd. All rights reserved.
• Molecular Taekwondo. 2. A New Calix[4]azacrown Bearing Two Different Binding Sites as a New Fluorescent Ionophore
  作者：Jong Seung Kim、Kwan Ho Noh、Seoung Ho Lee、Sung Kuk Kim、Sook Kyung Kim、Juyoung Yoon

  DOI：10.1021/jo020538i

  日期：2003.1.1

  Synthesis and binding studies of a new calixarene-based fluoroionophore were made. Calix[4]azacrown having an anthracenyl unit displayed large chelation-enhanced fluorescence effects with Cs+, Rb+, and K+ over other metal ion tested. Interesting "molecular taekwondo" processes between Cs+-Cu2+ and Cs+-Ag+ pairs were monitored via fluorescent changes.