5,11,17,23-tetra-tert-butyl-25,27-bis(hydroxycarbonylpropoxy)-26,28-dihydroxycalix[4]arene | 205995-83-1

• 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-tetra-tert-butyl-25,27-bis(hydroxycarbonylpropoxy)-26,28-dihydroxycalix[4]arene
• 英文别名: 5,11,17,23-tetra-tert-butyl-25,27-dicarxboxypropoxy-26,28-dihydroxycalix[4]arene；25,27-bis(hydroxycarbonylpropoxy)-p-tert-butylcalix[4]arene；4-[[5,11,17,23-Tetratert-butyl-27-(3-carboxypropoxy)-26,28-dihydroxy-25-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-dodecaenyl]oxy]butanoic acid
• CAS: 205995-83-1
• 化学式: C₅₂H₆₈O₈
• 分子量: 821.107
• InChiKey: DVPOSTUITUVGOT-UHFFFAOYSA-N

物化性质

• 熔点：
  248-250.5 °C
• 沸点：
  885.0±65.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  60
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-tert-butyl-25,27-bis(hydroxycarbonylpropoxy)-26,28-dihydroxycalix[4]arene 在 草酰氯 、 叠氮基三甲基硅烷 、 四丁基碘化铵 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 17.0h， 生成 5,11,17,23-tetra-tert-butyl-25,27-bis(isocyanatopropoxy)-26,28-dihydroxycalix[4]arene
  参考文献：
  名称：

  N-Linked Peptidocalix[4]arene Bisureas as Enantioselective Receptors for Amino Acid Derivatives

  摘要：

  Bisurea calix[4]arenes 1 and 2 possessing L-amino acid moieties at the lower rim were synthesized by reaction of the methyl esters of glycine, L-alanine, or L-isoleucine with the appropriate isocyanate (12 or 13), obtained with a safe and efficient Curtius rearrangement from the corresponding carboxylic acid derivatives. The conformational properties of the ligands 1 and 2 were investigated by means of a combined NMR and molecular modeling study which evidences that they are deeply influenced by strong intramolecular H-bonds between the urea NH groups and the vicinal phenolic oxygen atoms or the opposite urea CO group. Complexation studies performed by ESI-MS and NMR spectroscopy in acetone solution show that the binding ability of these bisurea hosts decreases by increasing the side chain size of the amino acid. Host 2b has a remarkable binding ability for the N-acetyl-D-phenylalaninate anion with an interesting enantioselectivity (K-ass(D)/K-ass(L) = 4.14), which is explained on the basis of a three-point interaction mode of binding.

  DOI：

  10.1021/jo062410x
• 作为产物：
  描述：

  5,11,17,23-tetra-tert-butyl-25,27-di(3-ethoxycarbonylpropoxy)-26,28-dihydroxycalix[4]arene 在 氢氧化钾 、 水 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 5,11,17,23-tetra-tert-butyl-25,27-bis(hydroxycarbonylpropoxy)-26,28-dihydroxycalix[4]arene
  参考文献：
  名称：

  Synthesis of Calix[4]arene-Cryptand Hybrid Systems: A New Generation of Hosts for Metal Ions and Molecules

  摘要：

  一种含有可衍生化次级氨基氮的穴醚已成功通过不同的间隔单元连接至杯[4]芳烃的下缘。

  DOI：

  10.1055/s-1998-1961

文献信息

• Calix[4]arene-Linked Bisporphyrin Hosts for Fullerenes:  Binding Strength, Solvation Effects, and Porphyrin−Fullerene Charge Transfer Bands
  作者：Ali Hosseini、Steven Taylor、Gianluca Accorsi、Nicola Armaroli、Christopher A. Reed、Peter D. W. Boyd

  DOI：10.1021/ja066031x

  日期：2006.12.1

  hosts for supramolecular binding of fullerene guests. Fullerene affinities were optimized by varying the nature of the covalent linkage of the porphyrins to the calixarenes. Binding constants for C60 and C70 in toluene were explored as a function of substituents at the periphery of the porphyrin, and 3,5-di-tert-butylphenyl groups gave rise to the highest fullerene affinities (26,000 M(-1) for C60). The

  杯[4]芳烃支架已被用于构建双卟啉（“颚”卟啉）宿主，用于富勒烯客体的超分子结合。通过改变卟啉与杯芳烃的共价键的性质，优化了富勒烯的亲和力。研究了甲苯中 C60 和 C70 的结合常数作为卟啉外围取代基的函数，3,5-二叔丁基苯基基团产生了最高的富勒烯亲和力（C60 为 26,000 M(-1)） . 这种高富勒烯亲和力的起源可以追溯到不同的溶剂化效应而不是电子效应。作为溶剂函数的结合常数的研究（甲苯 < 苯甲腈 < 二氯甲烷 < 环己烷）与富勒烯溶解度成反比，表明富勒烯的去溶剂化是决定结合常数大小的主要因素。富勒烯结合的能量学已根据 DelatH 和 DeltaS 确定，并且与焓驱动、溶剂化依赖过程一致。已经建立了富勒烯客体与双卟啉主体的超分子结合与宽 NIR 吸收带的出现之间的直接关系。该能带的能量作为卟啉电子结构的函数以可预测的方式移动，从而确定其起源于卟啉到富勒烯的电荷转移。已经建
• Lower-Rim-Substituted <i>tert</i>-Butylcalix[4]arenes; Part IX: One-Pot Synthesis of Calix[4]arene-Hydroxamates and Calix[4]arene-Amides
  作者：Maria Bocheńska、Urszula Lesińska

  DOI：10.1055/s-2006-942486

  日期：2006.8

  A simple method for selective acylation of protected and unprotected hydroxylamines with bis- and tetrakis-substituted p-tert-butylcalix[4]arene-acids through amide bond formation via mixed anhydrides is presented. The first crystal structure of calix-hydroxamate 1 is presented.

  提出了一种通过混合酸酐形成酰胺键，对保护和未保护的羟胺进行选择性酰化的简单方法，采用了双取代和四取代的对叔丁基钙克[4]芳酸。此外，首次提供了钙克羟肼化合物1的晶体结构。
• Studies on calix(aza)crowns, II. Synthesis of novel proximal doubly bridged calix[4]arenes by intramolecular ring closure of syn 1,3-and 1,2-ω-chloroalkylamides
  作者：István Bitter、Alajos Grün、Gábor Tóth、Barbara Balázs、Gyula Horváth、László Tõke

  DOI：10.1016/s0040-4020(98)00112-4

  日期：1998.4

  Inherently chiral calix[4]arenes (9,10) with carboxamide bridges spanning the proximal positions on the lower rim and 18 achiral counterparts have been synthesized by double intramolecular cyclization of 7b,8b 1,3-and 17 1,2-bis-chloroalkylamides. The conformational analysis of the 1.3- and 1,2-disubstituted calixarene intermediates 5–8 and 15–17 proved an equilibrium of two distorted cone conformations

  通过分子内双环化7b，8b 1,3-和17 1,2-bis-合成了手性杯[4]芳烃（9,10），其中羧酰胺桥跨越下缘的近端位置和18个非手性对应物。氯烷基酰胺。1.3-和1,2-二取代杯芳烃中间体5-8和15-17的构象分析证明了两个扭曲的圆锥构象的平衡。闭环的成功严格取决于开链前体的链长。
• Intriguing sensing properties of a di-tripodal amine calix[4]arene ionophore towards anions from Donnan failure in ion-selective membranes induced by Cu2+
  作者：Phetlada Kunthadee、Sarayut Watchasit、Arpadsara Kaowliew、Chomchai Suksai、Wanlapa Wongsan、Wittaya Ngeontae、Orawon Chailapakul、Wanlapa Aeungmaitrepirom、Thawatchai Tuntulani

  DOI：10.1039/c3nj00748k

  日期：——

  In this paper, di-tripodal amine calix[4]arene, L1, was successfully synthesized and used as an ion carrier in poly(vinyl chloride) (PVC) membrane electrodes. Compound L1 was employed to demonstrate a new concept in anion sensing by preparing an allosteric PVC membrane that can respond selectively to a certain anion in the presence of a metal effector. Membranes containing compounds L1 and potassium tetrakis(p-chlorophenyl)borate (KTpClPB) as an ionic additive showed Donnan exclusion failure upon measuring the potential (EMF) responses of Cu2+ and responded to the co-anion by giving negative EMF changes, while membranes containing compound L2, an anthracene-based mono-tripodal amine ligand, gave positive potentials to most metal ions. Upon preconditioning of the membranes containing L1 and 75 mol% KTpClPB in CuCl2, the membranes showed the highest selectivity towards thiocyanate with a near Nernstian slope of −59.6 mV decade−1, a 10−5 to 10−2 M linear range, and a detection limit of 4.4 × 10−6 M. The best allosteric membrane can be used in the pH range 3–7 with good reversibility, and also applied to indirectly determine the concentration of Fe3+ in aqueous solution.

  本文成功合成了二三叉胺钙[4]炔 L1，并将其用作聚氯乙烯（PVC）膜电极的离子载体。化合物 L1 被用于演示阴离子传感的新概念，即制备一种异构聚氯乙烯膜，在金属效应物存在的情况下，该膜可以对某种阴离子做出选择性反应。含有化合物 L1 和作为离子添加剂的四(对氯苯基)硼酸钾（KTpClPB）的膜在测量 Cu2+ 的电位（EMF）反应时显示出唐南排阻失效，并通过负 EMF 变化对共阴离子做出反应，而含有化合物 L2（一种蒽基单三足胺配体）的膜则对大多数金属离子给出正电位。在 CuCL2 中对含有 L1 和 75 mol% KTpClPB 的膜进行预处理后，膜对硫氰酸盐显示出最高的选择性，其斜率接近 Nernstian，为 -59.6 mV decade-1，线性范围为 10-5 至 10-2 M，检测限为 4.4 × 10-6 M。
• Calix[4]arenes C-136 and C-137 hyperpolarize myometrium mitochondria membranes
  作者：L. G. Babich、S. G. Shlykov、V. I. Boyko、M. A. Klyachina、S. A. Kosterin

  DOI：10.1134/s1068162013050026

  日期：2013.11

  Calixarenes are supramolecular compounds interacting with bioactive molecules and ions, causing changes in biochemical and biophysical processes. The aim of this work was to study the effects of calix[4]arenes C-136, C-137, and C-138 at the level of polarization of the rat myometrium mitochondria membrane. The structure of synthesized calix[4]arene molecules was confirmed by the methods of H-1 NMR and infrared spectroscopy. Calix[4]arenes C-136 and C-137 each possess two chalcone amide moieties at the lower rim, while calix[4]arene C-138, only one. Calix[4]arenes C-136 and C-137 differ by the presence of ether or hydroxyl groups, respectively, at the lower rim of calix[4]arene skeleton, as well as the length of alkyl spacer between chalcone amide group and the macrocycle. It was shown that calix[4]arenes C-136, C-137, and C-138 form micelles in aqueous medium and in dimethylformamide (DMF). Irradiation of micelles with an argon laser on the flow cytometer results in the rise of autofluorescence. In an aqueous medium, calix[4]arene micelles interact with a positively charged voltage-sensitive fluorescent probe TMRM, which can testify to the presence of negative charge in these structures. However, calix[4]arene micelles do not interact with TMRM in DMF solution. The mitochondrial membrane potential was measured using fluorescent dyes MTG and TMRM with confocal microscopy and fluorescent dye TMRM with flow cytometry. Experiments were conducted on myometrium cells in culture and on suspension of digitonin-permeabilized uterus myocytes. It was shown that the fluorescent signal was stable during the time of experiment. Calix[4]arenes C-136 and C-137 (10 mu M) hyperpolarize mitochondria membranes. At maximum, the effect was 173% relative to the control. At the same time, calix[4]arene C-138 did not influence the mitochondria membrane potential. The relationship between the structural organization of investigated calix[4]arene molecules and their effect on polarization of the mitochondria membrane is discussed.