Synthesis and Ultraviolet Absorption Characteristics of Chiral 3- arylidenenopinones from β-pinene

Author(s): Xu Xu, Yi-Qin Yang, Hai-Jun Xu, Lan Lan, Shi-Fa Wang

Journal Name: Letters in Drug Design & Discovery

Volume 11 , Issue 3 , 2014

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A new series of (1R,5R)-(-)-3-arylidenenopinones was synthesized from (1S,5S)-(-)-β-pinene which was a natural chemical from pine tree, and their ultraviolet absorption characteristics were investigated. (1R,5S)-(+)-nopinone was obtained from (1S,5S)-(-)-β-pinene by selective oxidation, and then it was reacted with benzaldehyde, phydroxybenzaldehyde, vanillin, o-vanillin, p-chlorobenzaldehyde, and p-methylaldehyde in the presence of alkali catalysts to get (1R,5R)-(-)-3-arylidenenopinones including (1R,5R)-(-)-3-benzylidenenopinone (1), (1R,5R)-(-)-3-(4′-hydroxybenzylidene) nopinone (2), (1R,5R)-(-)-3-(4′-hydroxy-3′-methoxybenzylidene)nopinone (3), (1R,5R)-(-)-3-(2′-hydroxy-3′- methoxybenzylidene)nopinone (4), (1R,5R)-(-)-3-(4′-chlorolbenzylidene)nopinone (5) (1R,5R)-(-)-3-(4′-methylbenzylidene) nopinone (6), and (1R,5R)-(-)-3-(furan-2′-ylmethylene)nopinone (7). The structures of (1R,5R)-(-)-3-arylidenenopinones were determined by FT-IR, 1H NMR, 13C NMR and GC-MS techniques. Their ultraviolet absorption characteristics and light stability was further examined. The results showed that compounds 1, 2, 5, 6 and 7 could be used as B-type UV absorbents, and compounds 3 and 4 had both functions as UV-A and UV-B types absorbents because of their wide range of UV absorption at 200-390 nm and 280-290 nm respectively. The light stability sequence of these compounds was (6)≈(7)>(3)>(5)>(2)>(1)>(4).

Keywords: (1S, 5S)-(-)-β-pinene, (1R, 5S)-(+)-nopinone, (1R, 5R)-(-)-3-arylidenenopinones, Ultraviolet absorbent, Selective oxidation, Light stability.

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Article Details

Year: 2014
Published on: 29 October, 2013
Page: [380 - 386]
Pages: 7
DOI: 10.2174/15701808113106660095
Price: $65

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