Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime
Fotohemijsko i Bekmanovo premeštanje(z)-holest-4-en-6-on oksima
Апстракт
Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime (4) (prepared in 4 steps starting from cholest-5-en-3β-ol ο1)) with thionyl chloride in dioxane solution afforded an enamide-type lactam, i.e. 7-aza-B-homocholest-4-en-6-one (6) as a single product. Photoreaction of the same compound in methanol or benzene-acetic acid solution gave a mixture of products, with the formation of the parent ketone 3 and the occurrence of Z/E isomerization, while the lactam 6 was obtained only when the reaction was performed in methanol and then in very low yield (7%).
Bekmanovo premeštanje (Z)-holest-4-en-6-on oksima (4) (koji je dobijen u 4 faze, polazeći od holest-5-en-3 β-ola (1)) sa tionil-hloridom u dioksanskom rastvoru, kao jedini proizvod daje laktam enamidnog tipa, tj. 7-aza-B-homoholest-4-en-6-on (6). Fotoreakcijom istog jedinjenja u metanolu ili u rastvoru benzen-sirćetna kiselina, nastaje smesa proizvoda koju čine polazni keton 3 i proizvodi Z/E izomerizacije, dok je laktam 6 dobiven u vrlo niskom prinosu (7%) samo u metanolnom rastvoru.
Кључне речи:
(Z)-cholest-4-en-6-one oxime / 7-aza-B-homocholest-4-en-6-one / Beckmann rearrangement / photoreactionИзвор:
Journal of the Serbian Chemical Society, 2004, 69, 6, 413-420Издавач:
- Serbian Chemical Society
DOI: 10.2298/JSC0406413K
ISSN: 0352-5139
WoS: 000222393300001
Scopus: 2-s2.0-4143050175
Институција/група
IHTMTY - JOUR AU - Krstić, Natalija AU - Bjelaković, Mira AU - Dabović, Milan AU - Lorenc, Ljubinka AU - Pavlović, Vladimir D. PY - 2004 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/148 AB - Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime (4) (prepared in 4 steps starting from cholest-5-en-3β-ol ο1)) with thionyl chloride in dioxane solution afforded an enamide-type lactam, i.e. 7-aza-B-homocholest-4-en-6-one (6) as a single product. Photoreaction of the same compound in methanol or benzene-acetic acid solution gave a mixture of products, with the formation of the parent ketone 3 and the occurrence of Z/E isomerization, while the lactam 6 was obtained only when the reaction was performed in methanol and then in very low yield (7%). AB - Bekmanovo premeštanje (Z)-holest-4-en-6-on oksima (4) (koji je dobijen u 4 faze, polazeći od holest-5-en-3 β-ola (1)) sa tionil-hloridom u dioksanskom rastvoru, kao jedini proizvod daje laktam enamidnog tipa, tj. 7-aza-B-homoholest-4-en-6-on (6). Fotoreakcijom istog jedinjenja u metanolu ili u rastvoru benzen-sirćetna kiselina, nastaje smesa proizvoda koju čine polazni keton 3 i proizvodi Z/E izomerizacije, dok je laktam 6 dobiven u vrlo niskom prinosu (7%) samo u metanolnom rastvoru. PB - Serbian Chemical Society T2 - Journal of the Serbian Chemical Society T1 - Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime T1 - Fotohemijsko i Bekmanovo premeštanje(z)-holest-4-en-6-on oksima VL - 69 IS - 6 SP - 413 EP - 420 DO - 10.2298/JSC0406413K ER -
@article{ author = "Krstić, Natalija and Bjelaković, Mira and Dabović, Milan and Lorenc, Ljubinka and Pavlović, Vladimir D.", year = "2004", abstract = "Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime (4) (prepared in 4 steps starting from cholest-5-en-3β-ol ο1)) with thionyl chloride in dioxane solution afforded an enamide-type lactam, i.e. 7-aza-B-homocholest-4-en-6-one (6) as a single product. Photoreaction of the same compound in methanol or benzene-acetic acid solution gave a mixture of products, with the formation of the parent ketone 3 and the occurrence of Z/E isomerization, while the lactam 6 was obtained only when the reaction was performed in methanol and then in very low yield (7%)., Bekmanovo premeštanje (Z)-holest-4-en-6-on oksima (4) (koji je dobijen u 4 faze, polazeći od holest-5-en-3 β-ola (1)) sa tionil-hloridom u dioksanskom rastvoru, kao jedini proizvod daje laktam enamidnog tipa, tj. 7-aza-B-homoholest-4-en-6-on (6). Fotoreakcijom istog jedinjenja u metanolu ili u rastvoru benzen-sirćetna kiselina, nastaje smesa proizvoda koju čine polazni keton 3 i proizvodi Z/E izomerizacije, dok je laktam 6 dobiven u vrlo niskom prinosu (7%) samo u metanolnom rastvoru.", publisher = "Serbian Chemical Society", journal = "Journal of the Serbian Chemical Society", title = "Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime, Fotohemijsko i Bekmanovo premeštanje(z)-holest-4-en-6-on oksima", volume = "69", number = "6", pages = "413-420", doi = "10.2298/JSC0406413K" }
Krstić, N., Bjelaković, M., Dabović, M., Lorenc, L.,& Pavlović, V. D.. (2004). Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime. in Journal of the Serbian Chemical Society Serbian Chemical Society., 69(6), 413-420. https://doi.org/10.2298/JSC0406413K
Krstić N, Bjelaković M, Dabović M, Lorenc L, Pavlović VD. Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime. in Journal of the Serbian Chemical Society. 2004;69(6):413-420. doi:10.2298/JSC0406413K .
Krstić, Natalija, Bjelaković, Mira, Dabović, Milan, Lorenc, Ljubinka, Pavlović, Vladimir D., "Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime" in Journal of the Serbian Chemical Society, 69, no. 6 (2004):413-420, https://doi.org/10.2298/JSC0406413K . .