引用本文:
刘长辉, 文瑞明, 雷雪松, 张哲. 茶螺烷酮合成的新工艺[J]. 应用化学,
2010, 27(10): 1238-1240.
doi:
10.3724/SP.J.1095.2010.90863
Citation: LIU Chang-Hui, WEN Rui-Ming, LEI Xue-Song, ZHANG Zhe. A New Synthetic Approach to Theaspirone[J]. Chinese Journal of Applied Chemistry, 2010, 27(10): 1238-1240. doi: 10.3724/SP.J.1095.2010.90863
Citation: LIU Chang-Hui, WEN Rui-Ming, LEI Xue-Song, ZHANG Zhe. A New Synthetic Approach to Theaspirone[J]. Chinese Journal of Applied Chemistry, 2010, 27(10): 1238-1240. doi: 10.3724/SP.J.1095.2010.90863
茶螺烷酮合成的新工艺
English
A New Synthetic Approach to Theaspirone
Abstract:
An edible perfume theaspirone,1-oxa-8-oxo-2,6,10,10-tetramethyl-spiro-[4,5]-6-decene,was synthesized from α-ionone with 52.6% overall yield via six steps including epoxiation by metachloroperbenzoic acid,ring-opening in the presence of sodium methoxide,selective reduction of carbon-carbon double bond catalyzed by Pd/C with ammoniumformate under ultrasonic irridiation,then reduction with sodium borohydride,intramolecular cyclodehydration and allylic oxidation catalyzed by acetylacetone cobalt(Ⅱ) with oxygen gas.The structures and compositions of the product and some intermediates were characterized by IR,1H NMR,MS and elemental analysis.
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Key words:
- theaspirone
- / ultrasonic irradiation
- / α-ionone
- / selective reduction
- / allylic oxidation
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