Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis
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2005
Authors
Bjelaković, Mira
Krstić, Natalija

Tinant, Bernard
Kalvoda, Jaroslav
Csanadi, Janos
Pavlović, Vladimir D.
Article (Published version)

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The conformations of (Z)‐ and (E)‐5‐oxo‐B‐nor‐5,10‐secocholest‐1(10)‐en‐3β‐yl acetates (2 and 3, resp.) were examined by a combination of X‐ray crystallographic analysis and NMR spectroscopy, with emphasis on the geometry of the cyclononenone moiety. The 1H‐ and 13C‐NMR spectra showed that the unsaturated nine‐membered ring of (E)‐isomer 3 in C6D6 and (D6)acetone solution exists in a sole conformation of type B1, which is similar to its solid‐state conformation. The (Z)‐isomer 2 in C6D6, CDCl3, and (D6)acetone solution, however, exists in two conformational forms of different families, with different orientation of the carbonyl group, the predominant form (85%) corresponding to the conformation of type A1 and the minor (15%) to the conformation A2 present also in the crystalline state. In this solid‐state conformations of the nine‐membered ring of both compounds, the 19‐Me and 5‐oxo groups are ‘β’‐oriented. The NMR analysis suggests that the nine‐membered ring of 4 has a conformation o...f type C1 in CDCl3 solution.
Keywords:
Conformations / X‐ray crystallographic analysis / NMR / SteroidsSource:
Helvetica Chimica Acta, 2005, 88, 10, 2812-2821Publisher:
- Wiley
DOI: 10.1002/hlca.200590221
ISSN: 0018-019X; 1522-2675
WoS: 000233154200025
Scopus: 2-s2.0-27644454700
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IHTMTY - JOUR AU - Bjelaković, Mira AU - Krstić, Natalija AU - Tinant, Bernard AU - Kalvoda, Jaroslav AU - Csanadi, Janos AU - Pavlović, Vladimir D. PY - 2005 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4186 AB - The conformations of (Z)‐ and (E)‐5‐oxo‐B‐nor‐5,10‐secocholest‐1(10)‐en‐3β‐yl acetates (2 and 3, resp.) were examined by a combination of X‐ray crystallographic analysis and NMR spectroscopy, with emphasis on the geometry of the cyclononenone moiety. The 1H‐ and 13C‐NMR spectra showed that the unsaturated nine‐membered ring of (E)‐isomer 3 in C6D6 and (D6)acetone solution exists in a sole conformation of type B1, which is similar to its solid‐state conformation. The (Z)‐isomer 2 in C6D6, CDCl3, and (D6)acetone solution, however, exists in two conformational forms of different families, with different orientation of the carbonyl group, the predominant form (85%) corresponding to the conformation of type A1 and the minor (15%) to the conformation A2 present also in the crystalline state. In this solid‐state conformations of the nine‐membered ring of both compounds, the 19‐Me and 5‐oxo groups are ‘β’‐oriented. The NMR analysis suggests that the nine‐membered ring of 4 has a conformation of type C1 in CDCl3 solution. PB - Wiley T2 - Helvetica Chimica Acta T1 - Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis VL - 88 IS - 10 SP - 2812 EP - 2821 DO - 10.1002/hlca.200590221 ER -
@article{ author = "Bjelaković, Mira and Krstić, Natalija and Tinant, Bernard and Kalvoda, Jaroslav and Csanadi, Janos and Pavlović, Vladimir D.", year = "2005", abstract = "The conformations of (Z)‐ and (E)‐5‐oxo‐B‐nor‐5,10‐secocholest‐1(10)‐en‐3β‐yl acetates (2 and 3, resp.) were examined by a combination of X‐ray crystallographic analysis and NMR spectroscopy, with emphasis on the geometry of the cyclononenone moiety. The 1H‐ and 13C‐NMR spectra showed that the unsaturated nine‐membered ring of (E)‐isomer 3 in C6D6 and (D6)acetone solution exists in a sole conformation of type B1, which is similar to its solid‐state conformation. The (Z)‐isomer 2 in C6D6, CDCl3, and (D6)acetone solution, however, exists in two conformational forms of different families, with different orientation of the carbonyl group, the predominant form (85%) corresponding to the conformation of type A1 and the minor (15%) to the conformation A2 present also in the crystalline state. In this solid‐state conformations of the nine‐membered ring of both compounds, the 19‐Me and 5‐oxo groups are ‘β’‐oriented. The NMR analysis suggests that the nine‐membered ring of 4 has a conformation of type C1 in CDCl3 solution.", publisher = "Wiley", journal = "Helvetica Chimica Acta", title = "Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis", volume = "88", number = "10", pages = "2812-2821", doi = "10.1002/hlca.200590221" }
Bjelaković, M., Krstić, N., Tinant, B., Kalvoda, J., Csanadi, J.,& Pavlović, Vladimir D.. (2005). Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis. in Helvetica Chimica Acta Wiley., 88(10), 2812-2821. https://doi.org/10.1002/hlca.200590221
Bjelaković M, Krstić N, Tinant B, Kalvoda J, Csanadi J, Pavlović V. Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis. in Helvetica Chimica Acta. 2005;88(10):2812-2821. doi:10.1002/hlca.200590221 .
Bjelaković, Mira, Krstić, Natalija, Tinant, Bernard, Kalvoda, Jaroslav, Csanadi, Janos, Pavlović, Vladimir D., "Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis" in Helvetica Chimica Acta, 88, no. 10 (2005):2812-2821, https://doi.org/10.1002/hlca.200590221 . .