S?ntese de 1,3-diarilpropanos
Autor(a) principal: | |
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Data de Publicação: | 1985 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFRRJ |
Texto Completo: | https://tede.ufrrj.br/jspui/handle/jspui/4340 |
Resumo: | This work describes the synthesis of three 1,3-diarylpropanes: 1-(2'-hydroxy-4'-methoxyphenyl)-3-(3"-hydroxy-4"-methoxyphenyl)-propane,1-(2',4'-dihydroxy-3',5'-dimethylphenyl)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-propane and 1-(2'-hydroxy-5'-methyl-4'-methoxyphenyl)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-propane. These compounds were synthesized with the purpose of confirming the proposed structures for the natural 1,3-diarylpropanes extracted from Virola multinervia, Iryanthera coriaceae and Iryanthera laevis. The synthetic pathway employed in this work involved the preparation of substituted acetophenones and benzaldehydes which, by aldol condensations, afforded the corresponding chalcones. These were submitted to catalytic hydrogenation (Pd-C, 10%) and Clemmensen reduction to give the title compounds which were characterised by I.R., 1H N.M.R. and Mass spectrometry. The comparison between the spectral data of the syntbetic 1,3-diarylpropancs and those of the natural products made it possible to confirm the structures for those compounds extracted from V. multinervia and I. coriaceae. Based on the fact that the spectral data of the synthetic product and those of the natural one obtained from I. laevis are not identical, a new structure is suggested for this 1,3-diaryl propane, namely, 1-(4'-hydroxy-2'-methoxyphenyl-5'-methyl)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-propane. |
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Braz Filho, RaimundoBraz Filho, Raimundopinto, Angelo da CunhaFerreira, Jos? Carlos NettoFraiz J?nior, Silas Varella2021-01-21T22:58:12Z1985-11-29FRAIZ J?NIOR, Silas Varella. S?ntese de 1,3-diarilpropanos. 1985. 147 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 1985.https://tede.ufrrj.br/jspui/handle/jspui/4340This work describes the synthesis of three 1,3-diarylpropanes: 1-(2'-hydroxy-4'-methoxyphenyl)-3-(3"-hydroxy-4"-methoxyphenyl)-propane,1-(2',4'-dihydroxy-3',5'-dimethylphenyl)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-propane and 1-(2'-hydroxy-5'-methyl-4'-methoxyphenyl)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-propane. These compounds were synthesized with the purpose of confirming the proposed structures for the natural 1,3-diarylpropanes extracted from Virola multinervia, Iryanthera coriaceae and Iryanthera laevis. The synthetic pathway employed in this work involved the preparation of substituted acetophenones and benzaldehydes which, by aldol condensations, afforded the corresponding chalcones. These were submitted to catalytic hydrogenation (Pd-C, 10%) and Clemmensen reduction to give the title compounds which were characterised by I.R., 1H N.M.R. and Mass spectrometry. The comparison between the spectral data of the syntbetic 1,3-diarylpropancs and those of the natural products made it possible to confirm the structures for those compounds extracted from V. multinervia and I. coriaceae. Based on the fact that the spectral data of the synthetic product and those of the natural one obtained from I. laevis are not identical, a new structure is suggested for this 1,3-diaryl propane, namely, 1-(4'-hydroxy-2'-methoxyphenyl-5'-methyl)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-propane.Neste trabalho s?o apresentadas as s?nteses de tr?s 1,3-diarilpropanos: 1-(2'-hidroxi-4'-metoxifenil)-3-(3"-hidroxi-4"-metoxifenil)-propano, 1-(2',4'-diidroxi-3',5'-dimetilfenil)-3-(2"-hidroxi-4",5"-metilenodioxifenil)-propano e 1-(2'-hidroxi-5'-metil-4'-metoxifenil)8-(2"-hidroxi-4,"5"-metilenodioxifenil)-propano. Estas subst?ncias foram sintetizadas com a finalidade de se comprovar as estruturas propostas para os 1,3-diarilpropanos naturais extra?dos de virola multinervia, Iryanthera coriaceae e Iryanthera laevis. O caminho sint?tico utilizado para a obten??o dessas subst?ncias envolveu a prepara??o de derivados de acetofenonas e benzalde?dos que, por condensa??o ald?lica, conduziram ? forma??o das chalconas correspondentes. Estas, por rea??es de redu??o apropriadas como hidrogena??o catal?tica com Pd-C (10%) e redu??o de Clemensen, foram transformadas nos respectivos 1,3-diarilpropanos. As subst?ncias foram caracterizadas com base nos espectros de IV, RMN de 1H e massas. A compara??o dos dados espectrais dos produtos sint?ticos com os dos produtos naturais permitiu comprovar as estruturas propostas para os 1,3-diarilpropanos extra?dos de V. multinervia, 1-(2'-hidroxi-4'-metoxifenil)-3-(3"-hidroxi-4"-metoxifenil)-propano, e de I. coriaceae, 1-(2',4'-diidroxi-3',5'-dimetilfenil)-3-(2"-hidroxi-4",5"-metilenodioxifenil)-propano, e reformular a estrutura proposta para o 1,3-diarilpropano extra?do de I. laevis. Esta estrutura deve ser reformulada devido a n?o identidade dos dados do produto sint?tico com os do natural. Pode-se propor a estrutura 1-(4'-hidroxi-5'-metil-2'-metoxifenil)-3-(2"-hidroxi-4",5"-metilenodioxifenil)-propano para este produto natural.Submitted by Jorge Silva (jorgelmsilva@ufrrj.br) on 2021-01-21T22:58:08Z No. of bitstreams: 1 1985 - Silas Varella Fraiz J?nior.pdf: 4253706 bytes, checksum: cc327d8827975c34514de66e2515b40e (MD5)Made available in DSpace on 2021-01-21T22:58:12Z (GMT). No. of bitstreams: 1 1985 - Silas Varella Fraiz J?nior.pdf: 4253706 bytes, checksum: cc327d8827975c34514de66e2515b40e (MD5) Previous issue date: 1985-11-29application/pdfhttps://tede.ufrrj.br/retrieve/63820/1985%20-%20Silas%20Varella%20Fraiz%20J%c3%banior.pdf.jpgporUniversidade Federal Rural do Rio de JaneiroPrograma de P?s-Gradua??o em Qu?micaUFRRJBrasilInstituto de Ci?ncias Exatas1,3-diarilpropanosS?nteseVirola multinerviaIryanthera coriaceaeIryanthera laevisQu?micaS?ntese de 1,3-diarilpropanosSynthesis of 1,3-diarylpropanesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFRRJinstname:Universidade Federal Rural do Rio de Janeiro (UFRRJ)instacron:UFRRJTHUMBNAIL1985 - Silas Varella Fraiz J?nior.pdf.jpg1985 - Silas Varella Fraiz J?nior.pdf.jpgimage/jpeg1987http://localhost:8080/tede/bitstream/jspui/4340/4/1985+-+Silas+Varella+Fraiz+J%C3%BAnior.pdf.jpga3466022ad6e956489bb7c11b93878e1MD54TEXT1985 - Silas Varella Fraiz J?nior.pdf.txt1985 - Silas Varella Fraiz J?nior.pdf.txttext/plain85843http://localhost:8080/tede/bitstream/jspui/4340/3/1985+-+Silas+Varella+Fraiz+J%C3%BAnior.pdf.txtcb5f628c5dd0295acef11b55636340dcMD53ORIGINAL1985 - Silas Varella Fraiz J?nior.pdf1985 - Silas Varella Fraiz J?nior.pdfapplication/pdf4253706http://localhost:8080/tede/bitstream/jspui/4340/2/1985+-+Silas+Varella+Fraiz+J%C3%BAnior.pdfcc327d8827975c34514de66e2515b40eMD52LICENSElicense.txtlicense.txttext/plain; charset=utf-82089http://localhost:8080/tede/bitstream/jspui/4340/1/license.txt7b5ba3d2445355f386edab96125d42b7MD51jspui/43402021-01-22 02:00:22.842oai:localhost: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Biblioteca Digital de Teses e Dissertaçõeshttps://tede.ufrrj.br/PUBhttps://tede.ufrrj.br/oai/requestbibliot@ufrrj.br||bibliot@ufrrj.bropendoar:2021-01-22T04:00:22Biblioteca Digital de Teses e Dissertações da UFRRJ - Universidade Federal Rural do Rio de Janeiro (UFRRJ)false |
dc.title.por.fl_str_mv |
S?ntese de 1,3-diarilpropanos |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 1,3-diarylpropanes |
title |
S?ntese de 1,3-diarilpropanos |
spellingShingle |
S?ntese de 1,3-diarilpropanos Fraiz J?nior, Silas Varella 1,3-diarilpropanos S?ntese Virola multinervia Iryanthera coriaceae Iryanthera laevis Qu?mica |
title_short |
S?ntese de 1,3-diarilpropanos |
title_full |
S?ntese de 1,3-diarilpropanos |
title_fullStr |
S?ntese de 1,3-diarilpropanos |
title_full_unstemmed |
S?ntese de 1,3-diarilpropanos |
title_sort |
S?ntese de 1,3-diarilpropanos |
author |
Fraiz J?nior, Silas Varella |
author_facet |
Fraiz J?nior, Silas Varella |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Braz Filho, Raimundo |
dc.contributor.referee1.fl_str_mv |
Braz Filho, Raimundo |
dc.contributor.referee2.fl_str_mv |
pinto, Angelo da Cunha |
dc.contributor.referee3.fl_str_mv |
Ferreira, Jos? Carlos Netto |
dc.contributor.author.fl_str_mv |
Fraiz J?nior, Silas Varella |
contributor_str_mv |
Braz Filho, Raimundo Braz Filho, Raimundo pinto, Angelo da Cunha Ferreira, Jos? Carlos Netto |
dc.subject.por.fl_str_mv |
1,3-diarilpropanos S?ntese Virola multinervia Iryanthera coriaceae Iryanthera laevis |
topic |
1,3-diarilpropanos S?ntese Virola multinervia Iryanthera coriaceae Iryanthera laevis Qu?mica |
dc.subject.cnpq.fl_str_mv |
Qu?mica |
description |
This work describes the synthesis of three 1,3-diarylpropanes: 1-(2'-hydroxy-4'-methoxyphenyl)-3-(3"-hydroxy-4"-methoxyphenyl)-propane,1-(2',4'-dihydroxy-3',5'-dimethylphenyl)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-propane and 1-(2'-hydroxy-5'-methyl-4'-methoxyphenyl)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-propane. These compounds were synthesized with the purpose of confirming the proposed structures for the natural 1,3-diarylpropanes extracted from Virola multinervia, Iryanthera coriaceae and Iryanthera laevis. The synthetic pathway employed in this work involved the preparation of substituted acetophenones and benzaldehydes which, by aldol condensations, afforded the corresponding chalcones. These were submitted to catalytic hydrogenation (Pd-C, 10%) and Clemmensen reduction to give the title compounds which were characterised by I.R., 1H N.M.R. and Mass spectrometry. The comparison between the spectral data of the syntbetic 1,3-diarylpropancs and those of the natural products made it possible to confirm the structures for those compounds extracted from V. multinervia and I. coriaceae. Based on the fact that the spectral data of the synthetic product and those of the natural one obtained from I. laevis are not identical, a new structure is suggested for this 1,3-diaryl propane, namely, 1-(4'-hydroxy-2'-methoxyphenyl-5'-methyl)-3-(2"-hydroxy-4",5"-methylenedioxyphenyl)-propane. |
publishDate |
1985 |
dc.date.issued.fl_str_mv |
1985-11-29 |
dc.date.accessioned.fl_str_mv |
2021-01-21T22:58:12Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
FRAIZ J?NIOR, Silas Varella. S?ntese de 1,3-diarilpropanos. 1985. 147 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 1985. |
dc.identifier.uri.fl_str_mv |
https://tede.ufrrj.br/jspui/handle/jspui/4340 |
identifier_str_mv |
FRAIZ J?NIOR, Silas Varella. S?ntese de 1,3-diarilpropanos. 1985. 147 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 1985. |
url |
https://tede.ufrrj.br/jspui/handle/jspui/4340 |
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por |
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por |
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Universidade Federal Rural do Rio de Janeiro |
dc.publisher.program.fl_str_mv |
Programa de P?s-Gradua??o em Qu?mica |
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UFRRJ |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Instituto de Ci?ncias Exatas |
publisher.none.fl_str_mv |
Universidade Federal Rural do Rio de Janeiro |
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