Facile Preparation and Molecular Structure of a Novel Metacyclophane |
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Authors: | Jing-Lei Zhang Qi Shi Jiang Wu |
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Institution: | Department of Medicinal Chemistry , School of Pharmacy, Fudan University , Shanghai, China |
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Abstract: | Abstract A novel 1,1,10,10,19,19-hexamethyl-5,14,23-trimethoxy3.3.3]metacyclophane (2) was prepared in 25% yield by Friedel–Crafts cyclization of 4-(2-methoxyphenyl)-2-methylbutan-2-ol (1) at ? 78 °C using TiCl4 as Lewis acid catalyst in anhydrous dichloromethane. The structure of cyclophane 2 was determined by single-crystal X-ray diffraction, and the impact of substrate concentration on the yield of macrocycle 2 was also examined. The study on the effect of substituents at the phenyl ring showed that the methoxy group in 1 is crucial for its trimerization to give the hexamethyl3.3.3]metacyclophane derivative. Demethylation of 2 with BBr3 gave 1,1,10,10,19,19-hexamethyl-5,14,23-trihydroxy3.3.3]metacyclophane (4) in 96% yield, and its three hydroxyl groups provide the possible modification sites for further construction of supramolecular assemblies. |
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Keywords: | 1-(3-Chloro-3-methylbutyl)-2-methoxybenzene Friedel-Crafts cyclization 1 1 10 10 19 19-hexamethyl-5 14 23-trimethoxy[3 3 3]metacyclophane 4-(2-methoxyphenyl)-2-methylbutan-2-ol |
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