Peracids oxidation of cholesta-5,8-dien-3β-yl acetate
Oksidacija holesta-5,8-dien-3β-il acetata sa perkiselinama
Апстракт
Expoxidation of cholesta-5,8-dien-3β-yl acetate (1) with peracids takes place preferentially at the more highly substituted Δ8-olefinic double bond to give: (a) with monoperphthalic acid, 8α,9α-epoxycholest-5-en-3β-yl acetate (2) (in 39 % yield) and 9α-hydroxy-5α,6α-epoxycholest-8(14)-en-3β-yl acetate (3) (in 30 % yield); and (b) with m-chloroperbenzoic acid, the 8α,9α-epoxide 2 (64 %) and 5α,6α-epoxy derivative 3 (20 %). Some chemical transformations of the obtained epoxides are described.
Epoksidacija holesta-5,8-dien-3β-il acetata (1) sa perkiselinama prvenstveno se odvija na više supstituisanoj Δ8-olefinskoj dvoguboj vezi pri čemu se dobija: (a) sa monoperftalnom kiselinom, 8α,9α-epoksiholest-5-en-3β-il acetat (2) (u prenosu od 39 %) i 9α-hidroksi-5α,6α-epoksiholest-8(14)-en-3β-il acetat (3) (u prenosu od 30 %); i (b) sa m-hlorperbenzoevom kiselinom, 8α,9α-epoksid 2 (u prenosu od 64 %) i 5α,6α-epoksi derivat 3 (u prenosu od 20 %). Opisane su i neke hemijske transformacije dobijenih epoksida.
Кључне речи:
cholesta-5,8-dien-3β-yl acetate / peracid oxidations / steroidal epoxides / reactivity ofИзвор:
Journal of the Serbian Chemical Society, 2000, 65, 11, 769-772Издавач:
- Serbian Chemical Society
Финансирање / пројекти:
- Project MESTD
Институција/група
IHTMTY - JOUR AU - Dabović, Milan AU - Petrović, Ivanka J. AU - Krstić, Natalija AU - Lorenc, Ljubinka PY - 2000 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/11 AB - Expoxidation of cholesta-5,8-dien-3β-yl acetate (1) with peracids takes place preferentially at the more highly substituted Δ8-olefinic double bond to give: (a) with monoperphthalic acid, 8α,9α-epoxycholest-5-en-3β-yl acetate (2) (in 39 % yield) and 9α-hydroxy-5α,6α-epoxycholest-8(14)-en-3β-yl acetate (3) (in 30 % yield); and (b) with m-chloroperbenzoic acid, the 8α,9α-epoxide 2 (64 %) and 5α,6α-epoxy derivative 3 (20 %). Some chemical transformations of the obtained epoxides are described. AB - Epoksidacija holesta-5,8-dien-3β-il acetata (1) sa perkiselinama prvenstveno se odvija na više supstituisanoj Δ8-olefinskoj dvoguboj vezi pri čemu se dobija: (a) sa monoperftalnom kiselinom, 8α,9α-epoksiholest-5-en-3β-il acetat (2) (u prenosu od 39 %) i 9α-hidroksi-5α,6α-epoksiholest-8(14)-en-3β-il acetat (3) (u prenosu od 30 %); i (b) sa m-hlorperbenzoevom kiselinom, 8α,9α-epoksid 2 (u prenosu od 64 %) i 5α,6α-epoksi derivat 3 (u prenosu od 20 %). Opisane su i neke hemijske transformacije dobijenih epoksida. PB - Serbian Chemical Society T2 - Journal of the Serbian Chemical Society T1 - Peracids oxidation of cholesta-5,8-dien-3β-yl acetate T1 - Oksidacija holesta-5,8-dien-3β-il acetata sa perkiselinama VL - 65 IS - 11 SP - 769 EP - 772 UR - https://hdl.handle.net/21.15107/rcub_cer_11 ER -
@article{ author = "Dabović, Milan and Petrović, Ivanka J. and Krstić, Natalija and Lorenc, Ljubinka", year = "2000", abstract = "Expoxidation of cholesta-5,8-dien-3β-yl acetate (1) with peracids takes place preferentially at the more highly substituted Δ8-olefinic double bond to give: (a) with monoperphthalic acid, 8α,9α-epoxycholest-5-en-3β-yl acetate (2) (in 39 % yield) and 9α-hydroxy-5α,6α-epoxycholest-8(14)-en-3β-yl acetate (3) (in 30 % yield); and (b) with m-chloroperbenzoic acid, the 8α,9α-epoxide 2 (64 %) and 5α,6α-epoxy derivative 3 (20 %). Some chemical transformations of the obtained epoxides are described., Epoksidacija holesta-5,8-dien-3β-il acetata (1) sa perkiselinama prvenstveno se odvija na više supstituisanoj Δ8-olefinskoj dvoguboj vezi pri čemu se dobija: (a) sa monoperftalnom kiselinom, 8α,9α-epoksiholest-5-en-3β-il acetat (2) (u prenosu od 39 %) i 9α-hidroksi-5α,6α-epoksiholest-8(14)-en-3β-il acetat (3) (u prenosu od 30 %); i (b) sa m-hlorperbenzoevom kiselinom, 8α,9α-epoksid 2 (u prenosu od 64 %) i 5α,6α-epoksi derivat 3 (u prenosu od 20 %). Opisane su i neke hemijske transformacije dobijenih epoksida.", publisher = "Serbian Chemical Society", journal = "Journal of the Serbian Chemical Society", title = "Peracids oxidation of cholesta-5,8-dien-3β-yl acetate, Oksidacija holesta-5,8-dien-3β-il acetata sa perkiselinama", volume = "65", number = "11", pages = "769-772", url = "https://hdl.handle.net/21.15107/rcub_cer_11" }
Dabović, M., Petrović, I. J., Krstić, N.,& Lorenc, L.. (2000). Peracids oxidation of cholesta-5,8-dien-3β-yl acetate. in Journal of the Serbian Chemical Society Serbian Chemical Society., 65(11), 769-772. https://hdl.handle.net/21.15107/rcub_cer_11
Dabović M, Petrović IJ, Krstić N, Lorenc L. Peracids oxidation of cholesta-5,8-dien-3β-yl acetate. in Journal of the Serbian Chemical Society. 2000;65(11):769-772. https://hdl.handle.net/21.15107/rcub_cer_11 .
Dabović, Milan, Petrović, Ivanka J., Krstić, Natalija, Lorenc, Ljubinka, "Peracids oxidation of cholesta-5,8-dien-3β-yl acetate" in Journal of the Serbian Chemical Society, 65, no. 11 (2000):769-772, https://hdl.handle.net/21.15107/rcub_cer_11 .