97600-49-2

Usage

Uses

Used in Chemical Synthesis:
O(1),O(3)-BIS(CARBETHOXYMETHYL)-P-TERT-BUTYLCALIX(4)ARENE is used as an intermediate in the synthesis of various fine chemicals, including amino acids and other specialty compounds. Its calixarene structure provides a platform for the attachment of functional groups, enabling the development of new molecules with specific properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, O(1),O(3)-BIS(CARBETHOXYMETHYL)-P-TERT-BUTYLCALIX(4)ARENE can be used as a building block for the development of new drug candidates. Its ability to form host-guest complexes with biologically relevant molecules may lead to the discovery of novel therapeutic agents with improved binding, selectivity, and efficacy.
Used in Supramolecular Chemistry:
O(1),O(3)-BIS(CARBETHOXYMETHYL)-P-TERT-BUTYLCALIX(4)ARENE is used as a key component in supramolecular chemistry, where it can be employed to construct molecular containers, sensors, and other functional materials. Its calixarene framework allows for the precise organization of molecular components, leading to the development of advanced materials with unique properties and applications.
Used in Analytical Chemistry:
In analytical chemistry, O(1),O(3)-BIS(CARBETHOXYMETHYL)-P-TERT-BUTYLCALIX(4)ARENE can be utilized as a selective receptor for the recognition and detection of specific analytes. Its calixarene structure enables the design of molecularly imprinted polymers and other sensing materials, which can be used for the selective capture and detection of target molecules in complex samples.

InChI:InChI=1/C52H68O8/c1-15-57-43(53)29-59-47-35-17-31-21-39(49(3,4)5)23-33(45(31)55)19-37-27-42(52(12,13)14)28-38(48(37)60-30-44(54)58-16-2)20-34-24-40(50(6,7)8)22-32(46(34)56)18-36(47)26-41(25-35)51(9,10)11/h21-28,55-56H,15-20,29-30H2,1-14H3

Upstream product

• 157432-87-6 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 
• 105-36-2 ethyl bromoacetate 
• 98-54-4 para-tert-butylphenol 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 1403456-66-5 C₆₄H₇₆N₄O₁₀ 
• 1529759-92-9 C₇₂H₈₂N₆O₈ 
• 1529759-94-1 C₇₂H₈₀Cl₂N₆O₈ 
• 1529759-93-0 C₇₂H₈₀F₂N₆O₈ 
• 1529759-95-2 C₇₄H₈₆N₆O₈ 
• 149775-71-3 25,27-Dimethoxy-26,28-bis(ethoxycarbonylmethoxy)-5,11,17,23-tetra-t-butylcalix<4>arene 

Relevant academic research and scientific papers

N -Alkyl calix[4]azacrowns for the selective extraction of uranium

The selective extraction of uranium by N-octylcalix[4]azacrown (NOCAC) and N-ethylhexylcalix[4]azacrown (NEHCAC) was investigated. The ligands were synthesised in three steps through the functionalisation of t-butyl calix[4]arene at the distal-1,3-positions of the lower rim with ethyl acetate groups followed by cyclisation with (imino)bis(ethane-2,1-diyl)diamide. A detailed investigation on the effect of various parameters, such as the aqueous phase acidity (sulfuric acid), the ionic strength, and ligand concentration, on the extraction of uranium(vi) has been conducted. The effect of the H2SO4 concentration has been studied from 0.02 to 3 M. Preliminary studies carried out on NOCAC in dodecane/octanol diluents showed that the uranium extraction from sulfuric acid is more efficient at a low H2SO4 concentrations. The stoichiometry of complexation was estimated from the slope method, NMR titration, and electrospray ionisation-mass spectrometry analysis. Both ligands were found to be highly selective for uranium(vi) over other competitive cations present in a simulated leach solution containing seven competitive cations. The successful recovery of the uranium from the organic phase has been performed thanks to stripping steps involving ammonium oxalate, ammonium carbonate, and sodium carbonate as stripping agents.

Hydroxyquinoline–Calix[4]arene Conjugates as Ligands for Polynuclear Lanthanide Complexes: Preparation, Characterization, and Properties of a Dinuclear EuIIIComplex

The synthesis of calixarene-based N4O4-donor ligand H6L, in which two 8-hydroxyquinoline-2-carbaldehyde units are appended via hydrazone-carbonylmethoxy linkages in a 1,3 arrangement to the lower rim of tert-butylcalix[4]arene, and its coordination properties towards EuIIIare described. The reaction of H6L with Eu(NO3)3·6H2O produced dinuclear complex [Eu2(H3L)2(MeCN)2] (4). The EuIIIions in 4 are well separated from each other (d > 8 ?) and each is coordinated by two tetradentate hydroxyquinoline-2-carbaldehyde hydrazone substituents from two triply deprotonated (H3L)3–ligands in a dodecahedral geometry. As a consequence there are no exchange interactions between the EuIIIions, and the magnetic properties are solely associated with thermal population of excited (7F1–7F6) terms. The spin–orbit coupling constant λ is 325.2(4) cm–1. Moreover, H6L was found to extract EuIIIand TbIIIfrom aqueous solution at pH 7–8, as established by radiotracing with160Tb and152Eu.

Non-trivial solution chemistry between amido-pyridylcalix[4]arenes and some metal salts

Mercury ion complexation reactions were carried out between 3 and various mercury(ii) salts. 1H NMR studies showed that the role of solvent, the anion chosen and the initial reaction conditions were critical and that the formation of a "simple" mercury(ii) complex was non-trivial. The mercury(ii) ion can cause either (i) the formation of an ion-pair system, which have a characteristic doubling of all signals in the 1H NMR spectrum, (ii) a cleavage reaction to occur resulting in the reformation of the calix[4]arene diester compound 2, but only when the reaction is heated and (iii) "simple" mercury binding to the pyridine rings when the binding studies are carried out using NMR titration techniques. The electrochemistry results, on the same systems, show that the initial reaction involves the removal of the phenoxide protons followed by the resulting catalysis of the mercury species. This proton removal is not observed in the NMR spectra of any of the mercury reactions. It was also found that 3 could bind silver and zinc salts and was not selective for mercury(ii) as was previously described. The Royal Society of Chemistry 2010.

Efficient synthesis of lower rim α-hydrazino tetrazolocalix[4]arenes via an Ugi-azide multicomponent reaction

In this study, we developed an efficient synthesis of α-hydrazino tetrazolocalix[4]arene derivatives in good yields under mild conditions via an Ugi-azide multicomponent reaction. Metal ion binding properties of one of the α-hydrazino tetrazolocalix[4]are

Synthesis, biological evaluation and molecular docking of calix[4]arene-based β-diketo derivatives as HIV-1 integrase inhibitors

In this publication, we design and report the synthesis of calix[4]arene-based β-diketo derivatives as novel HIV-1 integrase (IN) inhibitors. The target compounds were obtained using Claisen condensation, and their structures were characterized by NMR and

Synthesis and dichromate anion extraction ability of p-tert-butylcalix[4]arene diamide derivatives with different binding sites

The article describes the synthesis and evaluation of the dichromate anion (Cr2O72-/HCr2O7-) extraction properties of p-tert-butylcalix[4]arene diamide derivatives (5-7) containing different binding sites. Among these compounds, 6 and 7 have been synthesized via aminolysis in a toluene-methanol solvent system with 3-aminomethylpyridine and 3,6-dioxa-1,8-diamino octane, respectively. On the other hand, compound 5 has been synthesized via an acid chloride method due to its inefficiency under aminolysis. The extraction properties of these diamides toward dichromate anions are studied by liquid-liquid extraction. The results show that p-tert-butylcalix[4]arene diamide derivative 7 exhibited a much higher affinity toward dichromate anions than that of 6 due to its special structure, while 5 was an ineffective ligand for these anions.

Synthesis, electrochemical and intramolecular charge-transfer properties of 'calix[4]arene-acceptor' diad and triad derivatives

Calix[4]arenes substituted with various acceptor moieties (naphthoquinone (NQ), tetracyanoanthraquinodimethane (TCNAQ)) have been synthesized. In these derivatives the three-dimensional structure of calix[4]arene acts as a weak electron donor (D), connected via a linear sigma spacer to one or two electroactive acceptor (A) units. The electrochemical behavior of these derivatives has been studied by cyclic voltammetry. The UV-Vis spectrum of the TCNAQ triad (A-D-A, 13) reveals the presence of a weak intramolecular charge transfer absorption band.

A new Na+ sensor based on intramolecular fluorescence energy transfer derived from calix[4]arene

A new calix[4]arene having pyrene (as a donor) and anthroyloxy (as an acceptor) moieties at the lower rim has been synthesized as a fluorescent Na+ sensor based on intramolecular energy transfer.

Synthesis and characterisation of asymmetrically bridged calix[4]arene and tetrathiacalix[4]arene mono amido crown derivatives

The synthesis of asymmetrically bridged calix[4]arene and tetrathiacalix[4]arene amido crown derivatives has been achieved by the aminolysis of distal diester derivatives of calix[4]arene and tetrathiacalix[4]arene with 1,2-diaminopropane or 1,2-diaminocyclohexane (stereoisomeric mixture, mainly trans). The title compounds have been characterised by detailed analysis of their NMR spectra. The assignment of NMR signals and stereo differentiation in the amido crown ring formation has been studied using a chiral shift reagent.

Novel calix[4]arene based metallo-supramolecular complex for recognition of cyanide ions in aqueous medium

A novel bis-naphthalimidocalix[4]arene-Cu(II) supramolecular complex has been observed to provide an efficient recognition system for CN? ions in aqueous medium. The binding stoichiometry of bis-naphthalimidocalix[4]arene and copper ion has been found to be 1:1 while that for bis-naphthalimidocalix[4]arene-Cu(II) and cyanide ion it has been determined to be 1:2.