手性薄荷酮腙与一氧化氮反应产物的NMR谱研究

NMR Characterization of the Reaction Product of l-Menthone Hydrazone and Nitric Oxide

在温和条件下手性薄荷酮腙(1)与NO在痕量O2存在下发生偶氮-硝化反应,高选择性的生成α-硝基偶氮化合物.通过DEPT谱、1D NOE差谱和1 H-1 H COSY,HSQC等2DNMR技术对目标化合物2(2,4-二硝基苯基-1-硝基-(2-异丙基-5-甲基)环己基-二氮烯)的1 H,13 C NMR谱的信号进行了全归属和较详细的解析,确定了目标化合物2的结构.

A chiral 1-menthone hydrazone （1） reacted with nitric oxide in the presence of trace oxygen. This is a novel tandem nitration-azotization reaction, yielding α-nitro azo- compounds （2, E-l-（2-isopropyl-5-methyl-l-nitrocyclohexyl）-2-（2, 4-dinitrophenyl） di-azene） in high stereo selectivity. The structure of the reaction product was characterized by DEPT, 1D NOE and 2D NMR techniques including ^1H-^1H COSY and HSQC. The ^1H and 13^C NMR chemical shifts of the compound were assigned.