Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis
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 unsat...
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| Published in | Helvetica chimica acta Vol. 88; no. 10; pp. 2812 - 2821 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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Zürich
WILEY-VCH Verlag
01.10.2005
WILEY‐VCH Verlag |
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| 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. |
|---|---|
| AbstractList | Abstract
The conformations of (
Z
)‐ and (
E
)‐5‐oxo‐
B
‐nor‐5,10‐secocholest‐1(10)‐en‐3
β
‐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
1
H‐ and
13
C‐NMR spectra showed that the unsaturated nine‐membered ring of (
E
)‐isomer
3
in C
6
D
6
and (D
6
)acetone solution exists in a sole conformation of type
B
1
, which is similar to its solid‐state conformation. The (
Z
)‐isomer
2
in C
6
D
6
, CDCl
3
, and (D
6
)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
A
1
and the minor (15%) to the conformation
A
2
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
C
1
in CDCl
3
solution. 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. |
| Author | Krstić, Natalija M. Csanadi, Janos Tinant, Bernard Pavlović, Vladimir D. Kalvoda, Jaroslav Bjelaković, Mira S. |
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| Snippet | 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... Abstract The conformations of ( Z )‐ and ( E )‐5‐oxo‐ B ‐nor‐5,10‐secocholest‐1(10)‐en‐3 β ‐yl acetates ( 2 and 3 , resp.) were examined by a combination of... |
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| Title | Conformations of the Nine-Membered Ring in the B-Nor-5,10-secosteroids. X-Ray and NMR Analysis |
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