PHOTO-ISOMERIZATION OF AZADIRACHTIN STUDIED BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY COUPLED TO HIGH-FIELD PROTON NMR-SPECTROSCOPY

被引：35

作者：

JOHNSON, S ^{[1
]}

MORGAN, ED ^{[1
]}

WILSON, ID ^{[1
]}

SPRAUL, M ^{[1
]}

HOFMANN, M ^{[1
]}

机构：

[1] BRUKER ANALYT MESSTECH GMBH,D-76287 RHEINSTETTEN,GERMANY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 11期

关键词：

D O I：

10.1039/p19940001499

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Azadirachtin was irradiated with UV light, in both oxygen and nitrogen atmospheres. The reactions were followed by supercritical fluid chromatography (SFC) and the chromatograms showed that one photo-product was formed in both cases. High performance liquid chromatography coupled to high field proton NMR spectroscopy (HPLC-NMR) was used to identify the photo-product, The HPLC-NMR data indicated that the (E)-2-methylbut-2-enoate ester group had been converted into a (Z)-2-methylbut-2-enoate ester group. Confirmation was obtained by isomerizing methyl (E)-2-methylbut-2-enoate with UV light to form a mixture of geometric isomers and then recording the H-1 NMR shift for the alkene proton. Additional structural information was obtained from the isolated product, confirmed to be the (Z)-2-methylbut-2-enoate geometric isomer of azadirachtin.

引用

页码：1499 / 1502

页数：4

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