手性薄荷酮腙与一氧化氮反应产物的NMR谱研究

波谱学杂志 ›› 2012, Vol. 29 ›› Issue (3): 401-409.

手性薄荷酮腙与一氧化氮反应产物的NMR谱研究

杨得锁^*，罗小林

宝鸡文理学院化学化工系，陕西宝鸡 721013

收稿日期:2011-12-13 修回日期:2012-01-20 出版日期:2012-09-05 发布日期:2012-09-05
基金资助:
陕西省科技厅专项计划资助项目(2009K01-51），陕西省重点实验室重点科研资助项目(O5JS43).

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

YANG De-Suo^*, LUO Xiao-Lin

Department of Chemistry & Engineering, Baoji University of Arts & Science, Baoji 721013, China

Received:2011-12-13 Revised:2012-01-20 Online:2012-09-05 Published:2012-09-05
Supported by:
陕西省科技厅专项计划资助项目(2009K01-51），陕西省重点实验室重点科研资助项目(O5JS43).

摘要/Abstract

摘要：

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¹H-¹H COSY，HSQC等2D NMR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¹H，¹³C 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.

关键词: 核磁共振(NMR), 2D NMR, 薄荷酮腙, α-硝基偶氮化合物

Abstract:

A chiral l-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-1-(2-isopropyl-5-methyl-1-nitrocyclohexyl)-2-(2, 4-dinitrophenyl) diazene) 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 ¹³C NMR chemical shifts of the compound were assigned.

Key words: NMR, 2D NMR, l-menthone hydrazone, α-nitroazo-compounds

中图分类号:

O482.53

杨得锁, 罗小林. 手性薄荷酮腙与一氧化氮反应产物的NMR谱研究[J]. 波谱学杂志, 2012, 29(3): 401-409.

YANG De-Suo, LUO Xiao-Lin. NMR Characterization of the Reaction Product of l-Menthone Hydrazone and Nitric Oxide[J]. Chinese Journal of Magnetic Resonance, 2012, 29(3): 401-409.

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