SYNTHESIS AND NMR STRUCTURE DETERMINATION OF NEW LINEAR GERANYLPHENOLS BY DIRECT GERANYLATION OF ACTIVATED PHENOLS

The known geranylhydroquinone 2, geranylorcinol 4 and the derivative (E)-4-(3,7-dimethylocta-2,6-dienyl)-5-methylbenzene-1,3-diol 5, were prepared by Electrophilic Aromatic Substitution (EAS) reactions between the corresponding phenol derivatives containing electron-donor subtituents and geraniol us...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	TABORGA,LAUTARO, VERGARA,ALEJANDRA, FERNÁNDEZ,MARÍA JOSÉ, OSORIO,MAURICIO, CARVAJAL,MARCELA, MADRID,ALEJANDRO, MARILAF,FRANCISCO, CARRASCO,HÉCTOR, ESPINOZA CATALÁN,LUIS
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2013
Materias:	Linear geranylphenols synthesis NMR spectroscopy
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000200033
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:scielo:S0717-97072013000200033
record_format	dspace
spelling	oai:scielo:S0717-970720130002000332014-09-09SYNTHESIS AND NMR STRUCTURE DETERMINATION OF NEW LINEAR GERANYLPHENOLS BY DIRECT GERANYLATION OF ACTIVATED PHENOLSTABORGA,LAUTAROVERGARA,ALEJANDRAFERNÁNDEZ,MARÍA JOSÉOSORIO,MAURICIOCARVAJAL,MARCELAMADRID,ALEJANDROMARILAF,FRANCISCOCARRASCO,HÉCTORESPINOZA CATALÁN,LUIS Linear geranylphenols synthesis NMR spectroscopy The known geranylhydroquinone 2, geranylorcinol 4 and the derivative (E)-4-(3,7-dimethylocta-2,6-dienyl)-5-methylbenzene-1,3-diol 5, were prepared by Electrophilic Aromatic Substitution (EAS) reactions between the corresponding phenol derivatives containing electron-donor subtituents and geraniol using BF3XOEt2 as a catalyst. In addition, spectroscopic NMR information for 4 and 5 is complemented. Furthermore, the new (E)-2-(3,7-dimethylocta-2,6-dienyl) benzene-1,3,5-triol (geranylphloroglucinol) 13, (E)-2-(3,7-dimethylocta-2,6-dienyl)-1,3,5-trimethoxybenzene 14, (E)-2-(3,7-dimethylocta-2,6-dienyl)-6-methoxyphenol 15, (E)-3-(3,7-dimethylocta-2,6-dienyl)-2-methoxyphenol 16, (E)-5-(3,7-dimethylocta-2,6-dienyl)-2-methoxyphenol 17, (E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,3-diol 18, (E)-3-(3,7-dimethylocta-2,6-dienyl)benzene-1,2-diol 19, (E)-4-(3,7-dimethylocta-2,6-dienyl)-5-isopropyl-2-methylphenol 20, (E)-2-(3,7-dimethylocta-2,6-dienyl)-4-isopropyl-3-methylphenol 21, (E)-2-(3,7-dimethylocta-2,6-dienyl)-4-isopropyl-5-methylphenol 22, and(E)-2-tert-butyl-4-(3,7-dimethylocta-2,6-dienyl)-5-methylphenol 23 were also prepared with this synthesis strategy. All the synthesized compounds were fully characterized and their structures were established by IR, MS and mainly NMR spectroscopic dates.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.58 n.2 20132013-01-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000200033en10.4067/S0717-97072013000200033
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	Linear geranylphenols synthesis NMR spectroscopy
spellingShingle	Linear geranylphenols synthesis NMR spectroscopy TABORGA,LAUTARO VERGARA,ALEJANDRA FERNÁNDEZ,MARÍA JOSÉ OSORIO,MAURICIO CARVAJAL,MARCELA MADRID,ALEJANDRO MARILAF,FRANCISCO CARRASCO,HÉCTOR ESPINOZA CATALÁN,LUIS SYNTHESIS AND NMR STRUCTURE DETERMINATION OF NEW LINEAR GERANYLPHENOLS BY DIRECT GERANYLATION OF ACTIVATED PHENOLS
description	The known geranylhydroquinone 2, geranylorcinol 4 and the derivative (E)-4-(3,7-dimethylocta-2,6-dienyl)-5-methylbenzene-1,3-diol 5, were prepared by Electrophilic Aromatic Substitution (EAS) reactions between the corresponding phenol derivatives containing electron-donor subtituents and geraniol using BF3XOEt2 as a catalyst. In addition, spectroscopic NMR information for 4 and 5 is complemented. Furthermore, the new (E)-2-(3,7-dimethylocta-2,6-dienyl) benzene-1,3,5-triol (geranylphloroglucinol) 13, (E)-2-(3,7-dimethylocta-2,6-dienyl)-1,3,5-trimethoxybenzene 14, (E)-2-(3,7-dimethylocta-2,6-dienyl)-6-methoxyphenol 15, (E)-3-(3,7-dimethylocta-2,6-dienyl)-2-methoxyphenol 16, (E)-5-(3,7-dimethylocta-2,6-dienyl)-2-methoxyphenol 17, (E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,3-diol 18, (E)-3-(3,7-dimethylocta-2,6-dienyl)benzene-1,2-diol 19, (E)-4-(3,7-dimethylocta-2,6-dienyl)-5-isopropyl-2-methylphenol 20, (E)-2-(3,7-dimethylocta-2,6-dienyl)-4-isopropyl-3-methylphenol 21, (E)-2-(3,7-dimethylocta-2,6-dienyl)-4-isopropyl-5-methylphenol 22, and(E)-2-tert-butyl-4-(3,7-dimethylocta-2,6-dienyl)-5-methylphenol 23 were also prepared with this synthesis strategy. All the synthesized compounds were fully characterized and their structures were established by IR, MS and mainly NMR spectroscopic dates.
author	TABORGA,LAUTARO VERGARA,ALEJANDRA FERNÁNDEZ,MARÍA JOSÉ OSORIO,MAURICIO CARVAJAL,MARCELA MADRID,ALEJANDRO MARILAF,FRANCISCO CARRASCO,HÉCTOR ESPINOZA CATALÁN,LUIS
author_facet	TABORGA,LAUTARO VERGARA,ALEJANDRA FERNÁNDEZ,MARÍA JOSÉ OSORIO,MAURICIO CARVAJAL,MARCELA MADRID,ALEJANDRO MARILAF,FRANCISCO CARRASCO,HÉCTOR ESPINOZA CATALÁN,LUIS
author_sort	TABORGA,LAUTARO
title	SYNTHESIS AND NMR STRUCTURE DETERMINATION OF NEW LINEAR GERANYLPHENOLS BY DIRECT GERANYLATION OF ACTIVATED PHENOLS
title_short	SYNTHESIS AND NMR STRUCTURE DETERMINATION OF NEW LINEAR GERANYLPHENOLS BY DIRECT GERANYLATION OF ACTIVATED PHENOLS
title_full	SYNTHESIS AND NMR STRUCTURE DETERMINATION OF NEW LINEAR GERANYLPHENOLS BY DIRECT GERANYLATION OF ACTIVATED PHENOLS
title_fullStr	SYNTHESIS AND NMR STRUCTURE DETERMINATION OF NEW LINEAR GERANYLPHENOLS BY DIRECT GERANYLATION OF ACTIVATED PHENOLS
title_full_unstemmed	SYNTHESIS AND NMR STRUCTURE DETERMINATION OF NEW LINEAR GERANYLPHENOLS BY DIRECT GERANYLATION OF ACTIVATED PHENOLS
title_sort	synthesis and nmr structure determination of new linear geranylphenols by direct geranylation of activated phenols
publisher	Sociedad Chilena de Química
publishDate	2013
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000200033
work_keys_str_mv	AT taborgalautaro synthesisandnmrstructuredeterminationofnewlineargeranylphenolsbydirectgeranylationofactivatedphenols AT vergaraalejandra synthesisandnmrstructuredeterminationofnewlineargeranylphenolsbydirectgeranylationofactivatedphenols AT fernandezmariajose synthesisandnmrstructuredeterminationofnewlineargeranylphenolsbydirectgeranylationofactivatedphenols AT osoriomauricio synthesisandnmrstructuredeterminationofnewlineargeranylphenolsbydirectgeranylationofactivatedphenols AT carvajalmarcela synthesisandnmrstructuredeterminationofnewlineargeranylphenolsbydirectgeranylationofactivatedphenols AT madridalejandro synthesisandnmrstructuredeterminationofnewlineargeranylphenolsbydirectgeranylationofactivatedphenols AT marilaffrancisco synthesisandnmrstructuredeterminationofnewlineargeranylphenolsbydirectgeranylationofactivatedphenols AT carrascohector synthesisandnmrstructuredeterminationofnewlineargeranylphenolsbydirectgeranylationofactivatedphenols AT espinozacatalanluis synthesisandnmrstructuredeterminationofnewlineargeranylphenolsbydirectgeranylationofactivatedphenols
_version_	1718445490182291456

SYNTHESIS AND NMR STRUCTURE DETERMINATION OF NEW LINEAR GERANYLPHENOLS BY DIRECT GERANYLATION OF ACTIVATED PHENOLS

Ejemplares similares