Prikaz osnovnih podataka o dokumentu
Acid-catalyzed and photolytic reactivity of some unsaturated B-nor-5, 10-secosteroidal ketones
Kiselo-katalizovana i fotolitička reaktivnost nekih nezasićenih B-nor-5,10-sekosteroidnih ketona
dc.creator | Bjelaković, Mira | |
dc.creator | Pavlović, Vladimir D. | |
dc.creator | Dabović, Milan | |
dc.creator | Lorenc, Ljubinka | |
dc.date.accessioned | 2019-01-30T17:11:24Z | |
dc.date.available | 2019-01-30T17:11:24Z | |
dc.date.issued | 2003 | |
dc.identifier.issn | 0352-5139 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/115 | |
dc.description.abstract | The acid-catalyzed reaction of (Z)- and (E)-B-nor-5,10-seco-ketones 2 and 3 resulted in an intramolecular cyclization to give the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene derivative 8, the 5β-hydroxy-A-nor-1(10)-unsaturated compound 9 and the 5β,10β-dihydroxy A-nor-product 10, from the (Z)-isomer and the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene product 11, from the (E)-isomer. Upon UV-irradiation, the (Z)- and (E)-seco-ketones 2 and 3 underwent a reversible (Z)/(E) and (E)/(Z)-isomerization and in addition to a transannular photocyclization to afford the 10(19)-methylidene derivatives 8 and 11, respectively, while photolysis of the 10(19)-methylidene-B-nor-5,10-seco-ketone 4 gave the oxetane derivative 12. | en |
dc.description.abstract | Kiselo-katalizovana reakcija (Z)- i (E)-B-nor-5,10-seko-ketona 2 i 3 rezultuje u intramolekulskoj ciklizaciji dajući 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski derivat 8, 5β-hidroksi A-nor-1(10)-nezasićeno jedinjenje 9 i 5β,10β-dihidroksi-A-nor-proizvod 10, iz Z-izomera, i 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski proizvod 11, iz E-izomera. (Z)- i (E)-Seko- ketoni 2 i 3 UV-ozračivanjem podležu reverzibilnoj (Z)/(E) odnosno (E)/(Z) izomerizaciji, kao i transanularnoj fotociklizaciji dajući 10(19)-metilidenske derivate 8 odnosno 11, dok se fotolizom 10(19)-metilidenskog-5,10-seko-ketona 4 gradi oksetanski derivat 12. | sr |
dc.publisher | Serbian Chemical Society | |
dc.rights | openAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.source | Journal of the Serbian Chemical Society | |
dc.subject | (Z)- and (E)-B-nor-5,10-secosteroidal ketones | en |
dc.subject | 10(19)-methylidene-B-nor-5,10-secosteroidal ketone | en |
dc.subject | acid-catalyzed reactions | en |
dc.subject | photolytic reactions | en |
dc.subject | mechanistic interpretation | en |
dc.title | Acid-catalyzed and photolytic reactivity of some unsaturated B-nor-5, 10-secosteroidal ketones | en |
dc.title | Kiselo-katalizovana i fotolitička reaktivnost nekih nezasićenih B-nor-5,10-sekosteroidnih ketona | sr |
dc.type | article | |
dc.rights.license | BY-NC-ND | |
dcterms.abstract | Бјелаковић, Мира; Лоренц, Љубинка Б.; Дабовић, Милан М.; Павловић, Владимир Д.; Кисело-катализована и фотолитичка реактивност неких незасићених Б-нор-5,10-секостероидних кетона; Кисело-катализована и фотолитичка реактивност неких незасићених Б-нор-5,10-секостероидних кетона; | |
dc.citation.volume | 68 | |
dc.citation.issue | 4-5 | |
dc.citation.spage | 303 | |
dc.citation.epage | 312 | |
dc.citation.other | 68(4-5): 303-312 | |
dc.citation.rank | M23 | |
dc.identifier.doi | 10.2298/JSC0305303B | |
dc.identifier.fulltext | https://cer.ihtm.bg.ac.rs//bitstream/id/7679/113.pdf | |
dc.identifier.scopus | 2-s2.0-0037835592 | |
dc.identifier.wos | 000183423800009 | |
dc.type.version | publishedVersion |