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本文对强效镇痛剂羟甲芬太尼(OMF)八个对映异构体中的其中四个,即(-)-cis—(3R,4S,2′R)-OMF(l),(+)-cis-(3R,4S,2′S)-OMF (2),(+)-trans—(3S,4S,2′R)-OMF (3),和(+)—trans-(3S,4S,2′S)-OMF(4)进行了~1H NMR研究,归属了所有的共振谱线.对哌啶环质子间偶合常数的分析表明,所有顺式和反式异构体中的哌啶环都呈现相同的椅式构象.在顺式异构体中3-甲基位于直立键,而4-N-苯基丙酰胺基位于平伏键,反式异构体中它们均位于平伙键.讨论了3—甲基和4-N-苯基丙酰胺基的立体取代对NMR的影响,在顺式异构体中4—N—苯基丙酰胺基的构象相对固定,而在反式异构体中则较为自由.
Four of the eight enantiomers of potent analgesic oxymethaenamine (OMF), namely (-) - cis- (3R, 4S, 2’R) -OMF (+) - cis- (3R, 4S, 2’S) -OMF (2), (+) - trans- (3S, 4S, 2’R) -OMF 3S, 4S, 2’S) -OMF (4) were investigated by ~ 1H NMR and assigned to all the resonance spectra. The analysis of the coupling constants of the piperidine ring protons showed that all the cis and trans isomers Of the piperidine ring all present the same chair conformation In the cis isomer the 3-methyl is located in the upright bond and the 4-N-phenylpropionamido is in the equatorial, trans isomers which are all in the The effects of 3-methyl and 4-N-phenylpropionamido stereosubstitution on NMR were discussed, the conformation of 4-N-phenylpropionamido was relatively constant in the cis-isomer and In the trans isomer is more free.