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Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime

Fotohemijsko i Bekmanovo premeštanje(z)-holest-4-en-6-on oksima

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2004
146.pdf (118.6Kb)
Authors
Krstić, Natalija
Bjelaković, Mira
Dabović, Milan
Lorenc, Ljubinka
Pavlović, Vladimir D.
Article (Published version)
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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.
Keywords:
(Z)-cholest-4-en-6-one oxime / 7-aza-B-homocholest-4-en-6-one / Beckmann rearrangement / photoreaction
Source:
Journal of the Serbian Chemical Society, 2004, 69, 6, 413-420
Publisher:
  • Serbian Chemical Society

DOI: 10.2298/JSC0406413K

ISSN: 0352-5139

WoS: 000222393300001

Scopus: 2-s2.0-4143050175
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URI
https://cer.ihtm.bg.ac.rs/handle/123456789/148
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - 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 . .

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