Protona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?ides
Ano de defesa: | 2001 |
---|---|
Autor(a) principal: | |
Orientador(a): | , |
Banca de defesa: | , , , |
Tipo de documento: | Dissertação |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal Rural do Rio de Janeiro
|
Programa de Pós-Graduação: |
Programa de P?s-Gradua??o em Qu?mica
|
Departamento: |
Instituto de Ci?ncias Exatas
|
País: |
Brasil
|
Palavras-chave em Português: | |
Área do conhecimento CNPq: | |
Link de acesso: | https://tede.ufrrj.br/jspui/handle/jspui/4210 |
Resumo: | The increasing knowledge about the chemistry of synthetic pyrethroids resulted in the development of new, more selective, more effectives insecticides, which are inparallel less harmful to the environment. One know compound is esfenvalerate, which had strong impact on the coming up of modern insecticides. The activity of these molecules depends on asymmetric centers with defined configurations. In this work a synthetic route for the preparation of potent precursor for pyrethroids, the 2-(4'- chlorophenyl)-3-methylbutirate pantolactonyl ester via diastereoselective addition of R-(-)-pantolactone to phenylisopropylketene is presented (diastereoisomeric ratio 70:30). Studies to examine factors wich have influence on the stereoselectivity of this reactions have been performed. The aim of the preparation of these derivates was to open the possibility to use this route for the application in the synthesis for interesting biological molecules like the preparation of esfenvalerate analogous. |
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Castro, Rosane Norahttp://lattes.cnpq.br/5479814788308057Lima, Marco Edilson Freire dehttp://lattes.cnpq.br/8392420706762318Castro, Rosane Nora deS?rgio, PinheiroCosta, Jo?o Batista Neves daHelo?sa de, Mellohttp://lattes.cnpq.br/5504141768652868Fontes, Rosane Alves2020-11-26T16:09:36Z2001-05-17FONTES, Rosane Alves. Protona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?ides. 2001. 144 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 2001.https://tede.ufrrj.br/jspui/handle/jspui/4210The increasing knowledge about the chemistry of synthetic pyrethroids resulted in the development of new, more selective, more effectives insecticides, which are inparallel less harmful to the environment. One know compound is esfenvalerate, which had strong impact on the coming up of modern insecticides. The activity of these molecules depends on asymmetric centers with defined configurations. In this work a synthetic route for the preparation of potent precursor for pyrethroids, the 2-(4'- chlorophenyl)-3-methylbutirate pantolactonyl ester via diastereoselective addition of R-(-)-pantolactone to phenylisopropylketene is presented (diastereoisomeric ratio 70:30). Studies to examine factors wich have influence on the stereoselectivity of this reactions have been performed. The aim of the preparation of these derivates was to open the possibility to use this route for the application in the synthesis for interesting biological molecules like the preparation of esfenvalerate analogous.Na qu?mica de piretr?ides sint?ticos, a prepara??o de mol?culas que sejam mais seletivas, eficientes e que, conseq?entemente, contribuam para uma menor agress?o ao meio ambiente, tal como o esfenvalerato, tem contribu?do em muito para o advento dos inseticidas modernos. A atividade destas mol?culas depende da presen?a de centros assim?tricos com configura??es definidas. Neste trabalho apresentamos uma rota sint?tica para a prepara??o de um potente precursor na prepara??o de piretr?ides, o ?ster quiral 2-(4'-clorofenil)-3-metilbutirato de pantolactonila, obtido via rea??o de protona??o diastereosseletiva do derivado fenil-isopropilceteno com a R-(-)-pantolactona (raz?o diastereoisom?rica 70:30), onde foram estudados alguns fatores que influenciaram a diastereosseletividade da rea??o. O interesse na prepara??o de tais derivados reside no fato da possibilidade da sua aplica??o na s?ntese de mol?culas de interesse biol?gico, como no caso na prepara??o de an?logos ao esfenvalerato. xxiSubmitted by Celso Magalhaes (celsomagalhaes@ufrrj.br) on 2020-11-26T16:09:36Z No. of bitstreams: 1 2001 - Rosane Alves Fontes.pdf: 2129095 bytes, checksum: b10eafb394181db589c6d70fb1f65856 (MD5)Made available in DSpace on 2020-11-26T16:09:36Z (GMT). No. of bitstreams: 1 2001 - Rosane Alves Fontes.pdf: 2129095 bytes, checksum: b10eafb394181db589c6d70fb1f65856 (MD5) Previous issue date: 2001-05-17application/pdfhttps://tede.ufrrj.br/retrieve/63256/2001%20-%20Rosane%20Alves%20Fontes.pdf.jpgporUniversidade Federal Rural do Rio de JaneiroPrograma de P?s-Gradua??o em Qu?micaUFRRJBrasilInstituto de Ci?ncias Exataspiretr?ides sint?ticosqu?mica org?nicadiastereosseletividade da rea??oQu?micaProtona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?idesinfo: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:UFRRJTHUMBNAIL2001 - Rosane Alves Fontes.pdf.jpg2001 - Rosane Alves Fontes.pdf.jpgimage/jpeg2000http://localhost:8080/tede/bitstream/jspui/4210/4/2001+-+Rosane+Alves+Fontes.pdf.jpg2c74295a9e48f11e7b1ce02996a5c3f0MD54TEXT2001 - Rosane Alves Fontes.pdf.txt2001 - Rosane Alves Fontes.pdf.txttext/plain81081http://localhost:8080/tede/bitstream/jspui/4210/3/2001+-+Rosane+Alves+Fontes.pdf.txt5508b4c777d1f0e500942cc02b2df787MD53ORIGINAL2001 - Rosane Alves Fontes.pdf2001 - Rosane Alves Fontes.pdfapplication/pdf2129095http://localhost:8080/tede/bitstream/jspui/4210/2/2001+-+Rosane+Alves+Fontes.pdfb10eafb394181db589c6d70fb1f65856MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-82089http://localhost:8080/tede/bitstream/jspui/4210/1/license.txt7b5ba3d2445355f386edab96125d42b7MD51jspui/42102021-06-08 08:27:38.617oai: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:2021-06-08T11:27:38Biblioteca Digital de Teses e Dissertações da UFRRJ - Universidade Federal Rural do Rio de Janeiro (UFRRJ)false |
dc.title.por.fl_str_mv |
Protona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?ides |
title |
Protona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?ides |
spellingShingle |
Protona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?ides Fontes, Rosane Alves piretr?ides sint?ticos qu?mica org?nica diastereosseletividade da rea??o Qu?mica |
title_short |
Protona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?ides |
title_full |
Protona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?ides |
title_fullStr |
Protona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?ides |
title_full_unstemmed |
Protona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?ides |
title_sort |
Protona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?ides |
author |
Fontes, Rosane Alves |
author_facet |
Fontes, Rosane Alves |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Castro, Rosane Nora |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/5479814788308057 |
dc.contributor.advisor2.fl_str_mv |
Lima, Marco Edilson Freire de |
dc.contributor.advisor2Lattes.fl_str_mv |
http://lattes.cnpq.br/8392420706762318 |
dc.contributor.referee1.fl_str_mv |
Castro, Rosane Nora de |
dc.contributor.referee2.fl_str_mv |
S?rgio, Pinheiro |
dc.contributor.referee3.fl_str_mv |
Costa, Jo?o Batista Neves da |
dc.contributor.referee4.fl_str_mv |
Helo?sa de, Mello |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5504141768652868 |
dc.contributor.author.fl_str_mv |
Fontes, Rosane Alves |
contributor_str_mv |
Castro, Rosane Nora Lima, Marco Edilson Freire de Castro, Rosane Nora de S?rgio, Pinheiro Costa, Jo?o Batista Neves da Helo?sa de, Mello |
dc.subject.por.fl_str_mv |
piretr?ides sint?ticos qu?mica org?nica diastereosseletividade da rea??o |
topic |
piretr?ides sint?ticos qu?mica org?nica diastereosseletividade da rea??o Qu?mica |
dc.subject.cnpq.fl_str_mv |
Qu?mica |
description |
The increasing knowledge about the chemistry of synthetic pyrethroids resulted in the development of new, more selective, more effectives insecticides, which are inparallel less harmful to the environment. One know compound is esfenvalerate, which had strong impact on the coming up of modern insecticides. The activity of these molecules depends on asymmetric centers with defined configurations. In this work a synthetic route for the preparation of potent precursor for pyrethroids, the 2-(4'- chlorophenyl)-3-methylbutirate pantolactonyl ester via diastereoselective addition of R-(-)-pantolactone to phenylisopropylketene is presented (diastereoisomeric ratio 70:30). Studies to examine factors wich have influence on the stereoselectivity of this reactions have been performed. The aim of the preparation of these derivates was to open the possibility to use this route for the application in the synthesis for interesting biological molecules like the preparation of esfenvalerate analogous. |
publishDate |
2001 |
dc.date.issued.fl_str_mv |
2001-05-17 |
dc.date.accessioned.fl_str_mv |
2020-11-26T16:09:36Z |
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 |
FONTES, Rosane Alves. Protona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?ides. 2001. 144 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 2001. |
dc.identifier.uri.fl_str_mv |
https://tede.ufrrj.br/jspui/handle/jspui/4210 |
identifier_str_mv |
FONTES, Rosane Alves. Protona??o diastereosseletiva de alquil-aril cetenos na s?ntese de intermedi?rios para a prepara??o de piretr?ides. 2001. 144 f. Disserta??o (Mestrado em Qu?mica) - Instituto de Ci?ncias Exatas, Universidade Federal Rural do Rio de Janeiro, Serop?dica - RJ, 2001. |
url |
https://tede.ufrrj.br/jspui/handle/jspui/4210 |
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por |
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por |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Universidade Federal Rural do Rio de Janeiro |
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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 |
dc.source.none.fl_str_mv |
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