{"id":154673,"date":"2026-01-12T17:13:44","date_gmt":"2026-01-12T17:13:44","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/sintesis-de-3-11-dimetilalil-cumarinas\/"},"modified":"2026-01-12T17:13:44","modified_gmt":"2026-01-12T17:13:44","slug":"sintesis-de-3-11-dimetilalil-cumarinas","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/sintesis-de-3-11-dimetilalil-cumarinas\/","title":{"rendered":"Sintesis de 3-(1,1-dimetilalil) cumarinas"},"content":{"rendered":"<h2>Tesis doctoral de <strong> Rosario Hern\u00e1ndez Gal\u00e1n <\/strong><\/h2>\n<p>Las cumarinas constituyen un amplio grupo de productos naturales. Dentro de ellas, las preniladas en la posicion tres forman un interesante grupo debido al amplio rango de actividades biologicas que muestran. De entre estas actividades cabe destacar: la actividad citostatica, mostrada fundamentalmente por la rutamarina, actividad antifertilizante, espasmolitica y molusquicida.  dado que estos compuestos se obtienen de fuente natural en muy peque\u00f1as cantidades, hemos llevado a cabo la sintesis de las 3-(1,1-dimetilalil) cumarinas con anillos dihidropiranicos-piranicos y dihidrofuranicos-furanicos, tanto lineales como angulares. Para ello, hemos empleado dos metodos. El primero de ellos incluye como paso clave un reagrupamiento de claisen de un eter 3,3-dimetilalilico de la umbeliferona. Por este procedimiento hemos conseguido realizar la sintesis de las 3-(1,1-dimetilalil)cumarinas, llegando a interesantes conclusiones acerca del mecanismo por el cual transcurre dicha reaccion.  puesto que por el procedimiento anterior se obtenian 3-(1,1-dimetilalil) cumarinas en rendimientos moderados, hemos desarrollado un nuevo metodo, el cual consiste en:  apertura de la lactona, previamente hidrogenada para formar un ester 3,3-dimetilalilico, reagrupamiento de ireland-claisen seguido de lactonizacion oxidativa. Asi hemos sintetizado la 3-(1,1-dimetilalil)umbeliferona, angustifolina, en un rendimiento global del 50%.  hemos realizado ademas un estudio comparativo de rmn-c13 de cumarinas preniladas en el c-3 frente a los derivados no prenilados. Como consecuencia de la comparacion de los datos se observa diferencias significativas que permiten para cumarinas alquiladas en c-3, distinguir: dihidrofurano de dihidropiranos e isomeros dihidrofuranicos lineales de los angulares.<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>Sintesis de 3-(1,1-dimetilalil) cumarinas<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 Sintesis de 3-(1,1-dimetilalil) cumarinas <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Rosario Hern\u00e1ndez Gal\u00e1n <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 C\u00e1diz<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 01\/01\/1991<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<h3>Direcci\u00f3n y tribunal<\/h3>\n<ul>\n<li><strong>Director de la tesis<\/strong>\n<ul>\n<li>Javier Salva Garcia<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: Jose Fuentes Mota <\/li>\n<li>Braulio Manuel Fraga Gonz\u00e1lez (vocal)<\/li>\n<li>Guillermo Mart\u00ednez Massanet (vocal)<\/li>\n<li>Laurence Harwood (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Rosario Hern\u00e1ndez Gal\u00e1n Las cumarinas constituyen un amplio grupo de productos naturales. Dentro de ellas, las preniladas [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"var(--ast-global-color-4)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"tablet":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"mobile":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""}},"ast-content-background-meta":{"desktop":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"tablet":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"mobile":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""}},"footnotes":""},"categories":[1506,1412,17,416],"tags":[1888,1567,34507,10975,42032,47255],"class_list":["post-154673","post","type-post","status-publish","format-standard","hentry","category-cadiz","category-compuestos-heterociclicos","category-quimica","category-quimica-organica","tag-braulio-manuel-fraga-gonzalez","tag-guillermo-Martinez-massanet","tag-javier-salva-garcia","tag-jose-fuentes-mota","tag-laurence-harwood","tag-rosario-hernandez-galan"],"_links":{"self":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/posts\/154673","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/comments?post=154673"}],"version-history":[{"count":0,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/posts\/154673\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/media?parent=154673"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/categories?post=154673"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/tags?post=154673"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}