A NOVEL ROUTE TO CALIX[4]ARENES .2. SOLUTION-STATE AND SOLID-STATE STRUCTURAL-ANALYSES AND MOLECULAR MODELING STUDIES

被引:51
作者
BOTTA, B
DIGIOVANNI, MC
DELLEMONACHE, G
DE ROSA, MC
GACSBAITZ, E
BOTTA, M
CORELLI, F
TAFI, A
SANTINI, A
BENEDETTI, E
PEDONE, C
MISITI, D
机构
[1] DIPARTIMENTO FARMACO CHIM TECNOL, I-53100 SIENA, ITALY
[2] UNIV NAPOLI FEDERICO 2, DIPARTIMENTO CHIM, CIRPEB, I-80134 NAPLES, ITALY
[3] UNIV NAPOLI FEDERICO 2, CNR, CTR BIOCRISTALLOG, I-80134 NAPLES, ITALY
[4] UNIV CATTOLICA SACRO CUORE, CNR, CTR CHIM RECETTORI, I-00168 ROME, ITALY
[5] HUNGARIAN ACAD SCI, CENT RES INST CHEM, H-1525 BUDAPEST, HUNGARY
[6] UNIV NAPOLI FEDERICS 2, DIPARTIMENTO SCI ALIMENTI, I-80055 PORTICI, ITALY
关键词
D O I
10.1021/jo00085a047
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A versatile route to a series of C-alkylcalix[4]resorcinarenes has been developed, using 2,4-dimethoxycinnamates as starting materials under carefully controlled reaction conditions employing BF3 as a Lewis acid catalyst. Depending on the reaction conditions and the nature of the ester side chain in the cinnamates, the calixarenes can adopt 1,2-alternate, 1,3-alternate, or flattened-cone conformational states. An extensive study, relating to the influence of the Lewis acid, temperature, and reaction time, has provided information on the relative ratios of the different conformations and their interconversion. Structural assignments are based on detailed spectroscopic analyses including X-ray analyses. The latter provide evidence of their molecular structure and shape in the solid state. A detailed molecular modeling study has been completed and is described. From the data obtained, good agreement with NMR data, X-ray analyses and experimental results is observed.
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页码:1532 / 1541
页数:10
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