ISSN:
0749-1581
Schlagwort(e):
Morphine alkaloids
;
Isocodeines
;
Conformation of ring C
;
13C and 1H NMR
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Complete 1H and 13C NMR data are reported for eleven isocodeine and seven dihydroisocodeine derivatives bearing various substituents at position 6. In isocodeines having bulky succinimido or phthalimodo groups at C-6 ring C adopts a half-boat conformation, characterized by the quasi-equatorial orientation of the C-6—N bond. The distortion from the usual boat form is due to steric interactions between C-14 and β-substituents at C-6, and it is greater in 14-hydroxy derivatives than in isocodeines unsubstituted at this position. In dihydroisocodeines the conformation of ring C is close to a chair, irrespective of the steric demand of the substituent at C-6.
Zusätzliches Material:
5 Tab.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/mrc.1260300617
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