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1.
Osamu Morikawa 《Tetrahedron letters》2004,45(29):5731-5734
The cyclocondensation of an equimolar amount of 2-propylresorcinol with diethoxymethane in the presence of Sc(OTf)3 in acetonitrile produced a mixture of resorcin[n]arenes (n=4-7) with a kinetically controlled product distribution. However, the reaction with an excess amount of diethoxymethane produced the thermodynamically favored resorcin[4]arene as the major product. The fragmentation/recombination mechanism of the resorcin[n]arenes was discussed. 相似文献
2.
V. V. Glushko O. S. Serkova I. I. Levina V. I. Maslennikova 《Russian Journal of Organic Chemistry》2016,52(1):113-117
Directed modification of rctt-tetra-C-naphthyl resorcin[4]arene afforded a heterofunctionalized derivative containing specifically oriented phosphoryl and acetyl groups, and its ability to form complexes with organic amines was studied. The structure and stereochemistry of the resulting complexes depended on the amine nature. 相似文献
3.
Osamu Morikawa 《Tetrahedron letters》2006,47(24):3991-3994
The cyclocondensation of 1,3-dialkoxybenzenes with 1,3,5-trioxane was catalyzed by Sc(OTf)3 to produce resorcin[4]arene octaalkyl ethers as the major products. In addition, ‘confused’ resorcin[4]arene octaalkyl ethers bearing one alkoxy group at the intra-annular position were obtained as the minor products. The variable temperature 1H NMR spectroscopy showed that the alkoxy group at the intra-annular position cannot pass through the macrocyclic annulus, indicating a rigid molecular framework. The structure of the ethoxy derivative of the confused resorcin[4]arene was determined by X-ray crystallography. 相似文献
4.
Muriel Funck 《Tetrahedron letters》2010,51(49):6399-6402
A series of resorcin[4]arene and pyrogallol[4]arene macrocycles have been synthesized efficiently within 5 min, affording crystalline products suitable for single crystal X-ray diffraction, utilising microwave irradiation in a ‘one-pot’ reaction whilst controlling the selective formation of the rccc cone stereoisomer. 相似文献
5.
Covalently assembled resorcin[4]arenes and molecular tweezers: a chiral recognition rationale by NMR
Gloria Uccello Barretta Federica Balzano Federica Aiello Francesca Nardelli Alessia Ciogli Andrea Calcaterra 《Supramolecular chemistry》2016,28(7-8):647-655
Chiral diamides and tetramidic resorcin[4]arenes deriving from (R,R)-1,2-diaminocyclohexane and (S,S)-1,2-diphenylethylendiamine, and a valine containing resorcin[4]arene have been compared by NMR in the enantiodiscrimination of mandelic acid. The relevance of cooperation between side arms and external surface of resorcin[4]arene core has been ascertained. 相似文献
6.
Botta B Fraschetti C D'Acquarica I Sacco F Mattay J Letzel MC Speranza M 《Organic & biomolecular chemistry》2011,9(6):1717-1719
The gas-phase encounters between 2-aminobutane and proton-bound chiral resorcin[4]arene/nucleoside complexes behave in the gas phase as supramolecular "chiroselective logic gates" by releasing the nucleoside depending on the resorcin[4]arene and the 2-aminobutane configurations. 相似文献
7.
Osamu Morikawa 《Tetrahedron letters》2007,48(42):7489-7492
Mannich reaction of resorcin[4]arene with N,N′-diethylethylenediamine and formaldehyde produced a singly bridged resorcinarene-dimer bearing sixteen hydroxyl groups at their peripheral positions, which exists in a closed capsular conformation including the diazahexamethylene bridge chain between the two resorcinarene units in CD3OD. 相似文献
8.
Ali A. Husain Arthur M. Maknenko Prof. Dr. Kirpal S. Bisht 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(18):6223-6227
The synthesis of novel spatially directional multivalent resorcin[4]arene cavitand glycoconjugates (RCGs) and their ability to catalyze organic reactions is reported. The β‐d ‐glucopyranoside moieties on the upper rim of the “bowl”‐shaped resorcin[4]arene cavitand core are capable of multiple hydrogen‐bond interactions resulting in a pseudo‐cavity, which has been investigated for organic transformations in aqueous media. The RCGs have been demonstrated to catalyze thiazole formation, thiocyanation, copper(I)‐catalyzed azide alkyne cycloaddition (CuAAC), and Mannich reactions; they impart stereoselectivity in the three‐component Mannich reaction. Thermodynamic values obtained from 1H diffusion‐ordered spectroscopy (DOSY) experiments suggest that the upper saccharide cavity of the RCG and not the resorcin[4]arene cavity is the site of the complexation event. 相似文献
9.
Porphyrin conjugates were synthesized based on conformationally rigid, bowl shaped cavitand, and flexible unfirm resorcin[4]arenes. The influence of the resorcin[4]arene fragment on the porphyrin fluorescence is investigated. 相似文献
10.
Vinod K. Jain Parin H. Kanaiya 《Journal of inclusion phenomena and macrocyclic chemistry》2008,62(1-2):111-115
The tetraaminoresorcin[4]arene was synthesized, which otherwise could not be easily synthesized by conventional method, by first introducing the azo group at the upper rim, followed by its reduction with Na2S2O4. Tetraaminoresorcin[4]arene was then condensed with different aromatic aldehydes in ethanol at reflux temperature to obtain nine novel “upper rim” functionalized resorcin[4]arene Schiff-bases. All the nine Schiff-bases were characterized by m.p., elemental analysis, FT-IR, NMR and Mass spectral data. 相似文献
11.
Yoshinori EnmiKazuhiro Kobayashi Hisatoshi Konishi Minoru Morimoto 《Tetrahedron letters》2011,52(26):3367-3370
Thiomethylation of resorcin[4]arene using N,N-diisopropyl-2-aminoethanethiol hydrochloride and formaldehyde [1:4:4 molar ratio] carried out in methanol/acetic acid [1:1 v/v] at 60 °C produced monofunctionalized product 3 in 68% yield. The introduced substituent was intramolecularly self-included into the cavity. This self-inclusion reduced the reactivity of the aromatic rings and inhibited further functionalization. 相似文献
12.
Controlling the Size and Morphology of Supramolecular Assemblies of Viologen–Resorcin[4]arene Cavitands
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Dr. Ruslan R. Kashapov Dr. Sergey V. Kharlamov Elza D. Sultanova Rezeda K. Mukhitova Dr. Yuliana R. Kudryashova Prof. Dr. Lucia Y. Zakharova Dr. Albina Y. Ziganshina Prof. Dr. Alexander I. Konovalov 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(43):14018-14025
A novel class of self‐assembling nanoparticles is formed with viologen–resorcin[4]arene cavitands; the association model is strongly controlled by their hydrophobicity. Interestingly, the cavitand assemblies are designed through click chemistry to form self‐assembled noncovalently connected aggregates through counterion displacement. The iodide and benzoate ions are utilized as strongly polarizable counterions to induce cavitand self‐assembly. The counterion‐mediated decrease in hydrophilicity of the viologen–resorcin[4]arenes is the underlying trigger to induce particle formation. These particles can be used as nanocontainers and find their applications in delivery systems. 相似文献
13.
An efficient, straightforward and environmentally benign process has been developed for the synthesis of fluorenone and 1-tetralone derivatives using cyclic 1,3-dione, malononitrile and dialkylacetylenedicarboxylate as starting materials in aqueous medium. The reaction is favoured in presence of resorcin[4]arene which is effective as a reusable organocatalyst. The catalyst has been easily synthesized and characterized by 1H, 13C NMR, IR, XRD and HRMS analyses. Resorcin[4]arene afforded the resulted products in a shorter time and in good yields. The recyclability of the catalyst was established up to 6th cycle by FT-IR and SEM images. 相似文献
14.
Hisatoshi Konishi Rie Yokoyama Katsuhiro Hikawa Takehiro Nakada Kazuhiro Kobayashi Osamu Morikawa 《合成通讯》2013,43(5):605-610
Methylene-bridged resorcin[4]arene dimers were synthesized by the Sc(OTf)3-catalyzed hydroxymethylation of partially acetylated resorcin[4]arenes, and their preliminary complexation properties with tetraethylammonium ion were examined in CD3OD by 1H NMR spectroscopy. The dimers adopted a closed capsular conformation in this solvent and bound the guest molecule into their cavity. 相似文献
15.
The Mannich reaction between selectively tetratosylated resorcin[4]arene, formaldehyde and (S)-phenylalanine (or (S)-phenylglycine) methylamide gave cyclochiral mono- or dibenzoxazines with high diastereoselection as revealed by NMR and X-ray structural studies. X-ray structures of the products show the variety of intramolecular interactions that can be responsible for the diastereoselection of this acid-catalyzed reaction. 相似文献
16.
Botta B Botta M Filippi A Tafi A Delle Monache G Speranza M 《Journal of the American Chemical Society》2002,124(26):7658-7659
Gas-phase proton-bound complexes between a chiral resorcin[4]arene and some representative amino acids, that is, L- and D-alanine or L- and D-serine, were generated in the source of a Fourier transform ion cyclotron resonance mass spectrometer. Gas-phase exchange of the amino acid from the diastereomeric complexes with the enantiomers of 2-butylamine exhibits a significant enantioselectivity, which depends not only upon the configuration of the leaving guest but also on that of the incoming amine. These findings, coupled with molecular dynamic calculations, point to the observed gas-phase enantioselectivity as determined by the effects of the resorcin[4]arene chiral cavity upon the diastereomeric exchange transition structures. 相似文献
17.
Svetlana V. ShishkinaAndriy Tarnovskiy Vladimir RozhkovOleg V. Shishkin Oleg LukinAlexander Shivanyuk 《Tetrahedron》2012,68(46):9429-9434
In the crystalline state two molecules of resorcin[4]arene tetrabenzoates and four chloride anions form molecular wraps containing two Et3NH+ cations. The structure and composition of the wraps depend on the length of the alkyl chains at the narrow rim of the macrocycle. Resorcin[4]arene tetrabenzoates interact with ammonium salts in CDCl3. 相似文献
18.
Systematic Investigation of High‐Sensitivity Luminescent Sensing for Polyoxometalates and Iron(III) by MOFs Assembled with a New Resorcin[4]arene‐Functionalized Tetracarboxylate
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Dr. Shuai‐Tong Zhang Dr. Jin Yang Prof. Dr. Hua Wu Dr. Ying‐Ying Liu Prof. Dr. Jian‐Fang Ma 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(44):15806-15819
A new family of resorcin[4]arene‐based metal–organic frameworks (MOFs), namely, [Eu(HL)(DMF)(H2O)2] ? 3 H2O ( 1 ), [Tb(HL)(DMF)(H2O)2] 3 H2O ( 2 ), [Cd4(L)2(DMF)4(H2O)2] 3 H2O ( 3 ) and [Zn3(HL)2(H2O)2] 2 DMF ? 7 H2O ( 4 ), have been constructed from a new resorcin[4]arene‐functionalized tetracarboxylic acid (H4L=2,8,14,20‐tetra‐ethyl‐6,12,18,24‐tetra‐methoxy‐4,10,16,22‐tetra‐carboxy‐methoxy‐calix[4]arene). Isostructural 1 and 2 exhibit charming 1D motifs built with the cup‐like HL3? anions and rare earth cations. Compounds 3 and 4 show a unique sandwich‐based 2D layer and a fascinating 3D framework, respectively. Remarkably, compounds 1 and 2 display intensive red and green emissions triggered by the efficient antenna effect of organic ligands under UV light. More importantly, systematic luminescence studies demonstrate that Ln‐MOFs 1 and 2 , as efficient multifunctional fluorescent materials, show highly selective and sensitive sensing of Fe3+, polyoxometalates (POMs), and acetone, which represents a rare example of a sensor for quantitatively detecting three different types of analytes. This is also an exceedingly rare example of Fe3+ and POMs detection in aqueous solutions employing resorcin[4]arene‐based luminescent Ln‐MOFs. Furthermore, the possible mechanism of the sensing properties is deduced. 相似文献
19.
Cavitand-based anion receptors were developed by the introduction of four phenylurea moieties on the upper rim of a resorcin[4]arene. Their binding properties for various anions were investigated in DMSO-d6 using 1H NMR spectroscopic methods, and the high 1:1 binding affinity for carboxylates was observed due to hydrophobic as well as charge-dipole interactions between host and guest. 相似文献
20.
LIU Xiang LIU Yu-Jie ZHANG Qian-Feng 《结构化学》2005,24(7)
1 INTRODUCTION There is continuing interest in the assembly of molecular capsules based on concomitant formation of multiple hydrogen bonds between smaller mole- cular components[1]. A particularly attractive buil- ding block is calix[4]resorcinarenes with eight pen- dant hydroxyl functional groups[2]. In a crystal engi- neering design strategy for molecular self-assembly, cocrystallization of C-methylcalix[4]resorcinarenes with nitrogen-donor molecules such as pyridines in the presence … 相似文献