synthesis and dpph radical scavenging activity of prenylated phenol derivatives合成和dpph自由基清除活性prenylated酚衍生品.pdf

Molecules 2012, 17, 556-570; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis and DPPH Radical Scavenging Activity of Prenylated Phenol Derivatives Mauricio Osorio 1,*, Jacqueline Aravena 1, Alejandra Vergara 1, Lautaro Taborga 1, Evelyn Baeza 1, Karen Catalán 1, Cesar González 1, Marcela Carvajal 1, Héctor Carrasco 2 and 1 Luis Espinoza 1 Departamento de Química, Universidad Técnica Federico Santa María, Av. España N° 1680, Valparaíso, 2390123, Chile 2 Departamento de Ciencias Químicas, Universidad Andrés Bello, Campus Viña del Mar, Los Fresnos N 52, Viña del Mar, 2561156, Chile * Author to whom correspondence should be addressed; E-Mail: mauricio.osorio@usm.cl; Tel.: +56-32-265-4226. Received: 2 December 2011; in revised form: 27 December 2011 / Accepted: 4 January 2012 / Published: 6 January 2012 Abstract: The synthesis of twenty six prenylated phenols derivatives is reported. These compounds were obtained under mild conditions via Electrophilic Aromatic Substitution (EAS) coupling reactions between phenol derivatives containing electron-donor subtituents and 3-methyl-2-buten-1-ol using BF OEt . Dialkylations were also produced with this 3 2 method. The formation of a chroman ring by intramolecular cyclization between a sp2 carbon from the prenyl group with the hydroxyl substituent in the ortho position occurred with