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1.
Xian‐Shun Zeng Lin‐Hong Weng Lang‐Xing Chen Hong‐Fang Ju Xue‐Bing Leng Xi‐Wen He Zheng‐Zhi Zhang 《中国化学》2001,19(5):493-499
25, 25′, 27, 27′‐Bis(1,3‐dioxypropane)‐bis(5, 11, 17, 23‐tetra‐tert‐butylcalix[4]arene‐26,28‐diol) (4) and 25, 25′, 27, 27′‐bis(1, 4‐dioxybutane)‐bis (5, 11, 17, 23‐tetra‐tert‐butylcalix‐[4]arene‐26, 28‐diol) (5) were synthesized by the reaction of p‐tert‐butylcalix[4]arene (1) with preorganized 25, 27‐bis(3‐bromoproxyl)calix[4]arene‐26, 27‐diol (2) and 25, 27‐bis(3‐bromobutoxyl)calix[4]arene‐26, 27‐diol (3) in the presence of K2CO3 and KI. Compounds 4 and 5 were characterized with X‐ray analysis and the selectivity of 4 and 5 toward K+ over other alkali metal ions, alkaline metal ions as well as NH4+ were investigated with an ion‐selective electrode. 相似文献
2.
Cheng-Han KuoJun-Ren Huang Hui-Ru ChenPei-Yu Chen Chien-Hung LinLee-Gin Lin 《Tetrahedron》2011,67(21):3936-3944
Benzoylation of calix[4]arene monoalkyl ethers with benzoyl chloride yielded the corresponding 3-benzoates and/or 2,3-dibenzoates in different reaction conditions. A simple recrystallization process was able to isolate the 3-benzoates in good yield. In the presence of NaH as reaction base, the 1-alkoxy-3-benzoyloxycalixarenes were alkylated with active alkyl halides at proximal position and yielded the corresponding 1,2-dialkoxy derivatives. Basic hydrolysis of compounds afforded the expected 25,26-dialkoxycalix[4]arenes. For the less active alkyl halides, alkylation of 1-alkoxy-3-benzoyloxycalix[4]arenes afforded both the 1,2-dialkoxy derivatives and the benzoyl-migrated 1,3-dialkoxy derivatives. Only the highly symmetrical 1,3-diethoxy-2-benzoyloxycalix[4]arene was able to be isolated upon the deliberate recrystallization process. After basic hydrolysis of the dialkylated crude products, 25,26-dialkoxycalix[4]arenes were chromatographic separated. 相似文献
3.
A series of conformationally diverse novel tetrathiacalix[4]arene(amido)crowns and amides from tetrakis((ethoxycarbonyl)methoxy)p-tert-butyl tetrathiacalix[4]arene and its debutylated analog have been prepared by their reaction with diamines [H2N(CH2)nNH2; n=2,3,4, and 6] and polyamines. It has been determined that the length of the alkyl spacer in diamines is pivotal for the formation of either the tetrathiacalix[4]arene bis(amido)crowns or tetrathiacalix[4]arene amides with pendant amine functions. The synthesized compounds represent potential building blocks for achieving sophisticated molecular assemblies for molecular organization and recognition. Single crystal X-ray analysis of tetrathiacalix[4]arene bis(amido)crown 6a revealed that it has a 1,3-alternate conformation, which forms supramolecular complexes with chloroform. 相似文献
4.
Zhi-Feng Ye Zhi-Gang Pan Wei-Jiang He Xian-Fa Shi Long-Gen Zhu 《Journal of inclusion phenomena and macrocyclic chemistry》2001,40(1-2):89-93
Three new thiacalix[4]arene derivatives, 5,11,17,23-tetra-tert-butyl-25,27-di(2-hydroxyethoxy)-26,28-dihydroxythiacalix-{}[4]arene (2), 5,11,17,23-tetra-tert-25, 26,27,28-tetrakis[(methylcarboxyl)methoxy]thiacalix[4]arene (3),5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(2-hydroxy-1-propanoxy)thiacalix[4]arene (4), were synthesized for the first time. The coordination properties of thiacalix[4]arene(1) and its derivatives (2 and 4) were investigated by detecting the interactions betweenthese compounds and two palladium complexes, cis-[Pd(en)(H2O)2]2+ and cis-[Pd(dtco-3-OH)(H2O)2]2+, by means of electrospray ionization mass spectrometry (ESI-MS) technique. 相似文献
5.
Mine Sulak Ak Hasalettin Deligöz 《Journal of inclusion phenomena and macrocyclic chemistry》2006,55(3-4):223-228
Azocalix[4]arenes were prepared by linking 4-ethylaniline, 4-n-butylaniline, 4-acetamide aniline and 2-aminothiazol to calix[4]arene through a diazo-coupling reaction. A new family of azocalix[4]arenes, L1–L12, have been prepared by the incorporation of acetyl, benzoyl, and methyl ketone units to azocalix[4]arene. Characterization of the synthesized compounds was carried using elemental analyses, UV–Vis, IR and 1H NMR spectroscopic studies. 相似文献
6.
Ezgi AkceylanMustafa Yilmaz 《Tetrahedron》2011,67(34):6240-6245
This study reports the synthesis of calix[4]arene-based phase-transfer catalysts derived from the reaction of 5,17-di-tert-butyl-25,27,26,28-tetrahydroxycalix[4]arene with N-ethylpiperazine, diallylamine or 4-benzylpiperidine. The catalytic efficiency of the calix[4]arenes alkylamine derivatives was evaluated by carrying out the ester-forming reaction of alkali metal carboxylates (sodium butyrate or sodium caprylate) with p-nitrobenzyl bromide. It has been observed that the ester-forming reaction of alkali metal carboxylates with p-nitrobenzyl bromide, using the N-ethylpiperazine amine derivative of calix[4]arene as a phase-transfer catalyst in dichloromethane at 25 °C, provided the best yields. 相似文献
7.
Akiko Hori Erina Betsugi Yoshinori Ikumura Kenji Yoza 《Acta Crystallographica. Section C, Structural Chemistry》2019,75(3):265-270
Calix[4]arene and oxacalix[4]arene derivatives have eight possible conformations in the up and down directions of their four aromatic rings from the mean plane of a bridged central ring, the conformations of which determine the functionality of the host frameworks. Despite being a known compound for five decades, oxacalix[4]arene, C24H16O4, has not been characterized previously by crystallographic methods. It crystallizes from hexane/CH2Cl2 solution to give two polymorphs, i.e. prismatic and block‐shaped crystals as twisted 1,3‐alternate structures with S4 and C2 symmetry, respectively. These were previously suggested as the prefered stable conformations by density functional theory (DFT) calculations. 相似文献
8.
Various operating conditions have been applied on tetrakis[p‐(halogenomethyl)]‐ and tetrakis[p‐(aminomethyl)]calix[4]arene derivatives to improve the synthesis of the 5,11,17,23‐tetrakis[(diethylphosphono)methyl]‐25,26,27,28‐tetrahydroxycalix[4]arene. Two new, high yield, synthetic pathways have been selected, involving, for the first one, the 25,26,27,28‐tetrahydroxy‐5,11,17,23‐tetrakis[(trimethylamino)methyl]calix[4]arene, tetraiodide, DMF, and 10 equiv. of triethyl phosphite ((EtO)3P), and, for the other one, the 5,11,17,23‐tetra(bromomethyl)‐25,26,27,28‐tetrahydroxycalix[4]arene, CH2Cl2, and only 4 equiv. of (EtO)2P. 相似文献
9.
A. N. Novikov V. A. Bacherikov Yu. E. Shapiro A. I. Gren 《Journal of Structural Chemistry》2006,47(6):1003-1015
The cone conformation of C 4 symmetry is shown by the Hartree-Fock method (3-21G basis) to be the predominant conformer of calix[4]arene; the compressed cone of C 2 symmetry is the major conformer of calix[6]arene. Using quantum chemical methods we calculated hydrogen bond cleavage energies for calix[4]-(ab initio and density functional methods) and calix[6]arene (ab initio), and also for the complex of calix[4]arene with carbon disulfide. These energies along with structural data point to the cooperative effect of hydrogen bonds. The results of these studies provided an explanation to the greater conformational lability of calix[6]arene compared with calix[4]arene molecules. It is also predicted that the nucleophilic substitution reaction involving calix[6]arene in the presence of weak bases and in aprotic solvents, as well as in the gas phase, will occur via diastereomeric transition states. 相似文献
10.
Cone, partial cone and 1,3-alternate conformers of tetrathiacalix[4]arene tetraethylacetate were synthesized and subjected to aminolysis with alkyl amines [CH3(CH2)nNH2; n=2, 3, 5] to yield mono-, di-, tri- or tetrasubstituted p-tert-butyltetrathiacalix[4]arene amides which were characterized by detailed analysis of their NMR spectral and single crystal X-ray crystallography. It has been observed that while the 1,3-alternate and cone conformers of the tetrathiacalix[4]arene tetraethylacetate gave corresponding tetrathiacalix[4]arene tetraamides under different experimental conditions, the corresponding partial cone conformer undergoes a cascade of regioselective reactions with the same amines. Variable temperature 1H NMR experiments allowed the determination of relative stability of different conformers within the temperature range of 298-333 K. The synthesized derivatives were evaluated as molecular extractants for cations and anions and were determined to facilitate extraction of oxyanions (CrO42− and Cr2O72−) from aqueous to the organic phase. The studies have a significance in the design of tetrathiacalix[n]arene based molecular receptors for innovative applications. 相似文献
11.
Serkan Sayin Gülderen Uysal Akkuş Radek Cibulka Ivan Stibor Mustafa Yilmaz 《Helvetica chimica acta》2011,94(3):481-486
The synthesis of two new flavin substituted calix[4]arene derivatives, 9 and 10 , is described. The first flavin substituted calix[4]arene derivative 9 was synthesized by the reaction of 3‐methylalloxazine ( 5 ) with 25,27‐bis(3‐bromopropoxy)‐26,28‐dihydroxy‐5,11,17,23‐tetra(tert‐butyl)calix[4]arene ( 4 ) in high yield (92%). The other derivative 10 was prepared from 3‐methylalloxazine‐1‐acetic acid ( 7 ) and 25,27‐bis(3‐cyanopropoxy)calix[4]arene ( 3 ). All new compounds were characterized by a combination of FT‐IR and 1H‐NMR spectroscopy, and elemental‐analysis techniques. 相似文献
12.
Abdelhalim Guelzim Mohamed Saadioui Zouhair Asfari Jacques Vicens 《Journal of inclusion phenomena and macrocyclic chemistry》2001,39(1-2):91-95
The synthesis of25-[2-(ethoxy-1-p-toluene-sulfonate)phenyl]-26,27,28-trihydroxy calix[4]arene3 as a byproduct of the preparation of 1,3-dialkylated25,27-di-[2-(ethoxy-1p-toluene-sulfonate)phenyl]-26,28-dihydroxy calix[4]arene 2 is reported. Compound 3 is a monoalkylatedcalix[4]arene in the cone conformation. The X-ray structure of 3 showed that this conformation is stabilized by intramolecular hydrogen bonding. 相似文献
13.
逐步法合成杯[4]芳烃关环反应的改进 总被引:2,自引:0,他引:2
对位带有3种或4种不同取代基的杯「4]芳烃一般通过逐步合成法合成.50年代后期,wS和Hllfl比rI'·'a就用[1十1十1十工]的逐步法9步合成出了杯[4]芳烃,总产率相当低·1979年B6hmer等['·'报道用对位取代酚的线型三聚体与2,6一双溪甲基对取代酚在乙酸中进行关环反应合成杯[4」芳烃,这种[3+l」的逐步法只需3步连续反应就能合成带有3种不同取代基的杯卜」芳烃,但最后。步关环产率仍然很低(2%、15%)[".后来*dhmeTD'等将关环反应改进为在TICI。/二氧六环体系中进行,产率有所提高,这种逐步法曾用于不对称杯[4」芳烃的… 相似文献
14.
In this study, 5,11,17,23-tetrakis[(N-ethylpiperazine)methyl]-25,26,27,28-tetrahydroxycalix[4]arene (3) and 5,11,17,23-tetrakis[(4-carboethoxy-N-piperidino) methyl]-25,26,27,28-tetrahydroxycalix[4]arene (4) were synthesized in one step according to the Mannich reaction by the treatment of calix[4]arene with a secondary amine (N-ethylpiperazine, ethyl-4-piperidincarboxylate) and formaldehyde. The calix[4]arene derivatives (3, 4) were characterized by a combination of FTIR, 1H NMR and elemental analyses. The synthesized compounds were used in an esterification reaction as the phase transfer catalyst. The catalytic efficiency of the calix[4]arenes 3 and 4 was evaluated by carrying out the ester-forming reaction of alkali metal carboxylates (sodium butyrate or sodium caprylate) with p-nitrobenzyl bromide. It was observed that the ester-forming reaction of alkali metal carboxylates with p-nitrobenzyl bromide, using calix[4]arene-based catalyst 3 as a phase-transfer catalyst in dichloromethan, provided the best yields. 相似文献
15.
The p-nitrophenylazo calix[4] arene derivatives la-ld with nonlinear optical(NLO)properties were prepared by the diazo-coupling reaction of calix[4]arene with p-nitrophenyl diazonium.The diazotization reaction of p-nltroaniline was caried out with isoamyl nitrite as a source of nitrous acid in EtONa/EtOH under refluxing conditon.X-Ray crystallographic analysis and ^1H NMR sptectra reveal that they exist as cone conformation in crystal state or in soution.HRS measurements at 1064 nm in THF indicate that p-nitrophenylazo calix[4]arenes have higher hyperpolarizability βz values than the corresponding reference compound 4-(4-nitrophenylazo)-2,6-dimethyl-phenol,without red shift of the charge transfer band.The tetrakis p-nitropheylazo calix[4]arene(2)with longer alkyl chains can form monolayer aht the air/water interface. 相似文献
16.
17.
Novel calix[4]arene amides have been synthesized and their interaction with alkaline cations has been evaluated through extracting aqueous solutions of Li-, Na- and K-picrates with solutions of calix[4]arene amides in CH2Cl2. Electron-withdrawing groups on the upper rim of the calix[4]arene scaffold were found to have a negative effect on the absolute amount of metal ions extracted. The decreased extraction ability is accompanied by a higher selectivity towards sodium cations. 相似文献
18.
19.
新型杯芳烃为载体的铅离子选择电极 总被引:2,自引:0,他引:2
报道了5,11,17,23-四(1,1-二甲基乙基)-25,27-二羟基-26,28-二[(2-丙酰胺)乙氧基]杯[4]芳烃1的合成及以此化合物为载体研制了PVC膜铅离子选择电极。研究了不同极性的膜增塑剂和亲脂性阴离子位点对铅离子选择电极响应性能的影响,测定了铅离子选择电极的性能。铅离子选择电极对铅离子表现出优良的能斯特响应和高选择性,能在pH4.0-6.5的范围内使用,该电极可作为电位滴定的指示电极。 相似文献
20.
A New Efficient Synthesis of p-Nitrocalix[4]arene 总被引:1,自引:0,他引:1
YongLI JiaSongWANG QiWANG DeShanLI 《中国化学快报》2004,15(4):400-403
A new efficient synthesis of p-nitrocalix[4]arene from calix[4]arene by using nitrogen dioxide is described.The compound is an useful intermediates for the introduction of other functional groups to obtain N containing substituted calix[4]arene.The reaction mechanism is briefly discussed. 相似文献