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

[ Vol. 11 , Issue. 3 ]


Xu Xu, Yi-Qin Yang, Hai-Jun Xu, Lan Lan and Shi-Fa Wang   Pages 380 - 386 ( 7 )


A new series of (1R,5R)-(-)-3-arylidenenopinones was synthesized from (1S,5S)-(-)-&#946;-pinene which was a natural chemical from pine tree, and their ultraviolet absorption characteristics were investigated. (1R,5S)-(+)-nopinone was obtained from (1S,5S)-(-)-&#946;-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, <sup>1</sup>H NMR, <sup>13</sup>C 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).


(1S,5S)-(-)-&#946;-pinene, (1R,5S)-(+)-nopinone, (1R,5R)-(-)-3-arylidenenopinones, Ultraviolet absorbent, Selective oxidation, Light stability.


, , , , Institute of Chemical Engineering, Nanjing Forestry University, Nanjing, Jiangsu 210037, People’s Republic of China.

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