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左旋β蒎烯选择性氧化合成右旋诺蒎酮的研究(PDF)

《南京林业大学学报(自然科学版)》[ISSN:1000-2006/CN:32-1161/S]

Issue:
2010年02期
Page:
89-94
Column:
研究论文
publishdate:
2010-03-30

Article Info:/Info

Title:
Synthesis of (+)nopinone from (-)βpinene by selective oxidation
Author(s):
LIU Bing AO Wangwei YANG Yang WANG Shifa*
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
Keywords:
(-)βpinene selective oxidation (+)nopinone
Classification number :
TQ351
DOI:
10.3969/j.jssn.1000-2006.2010.02.021
Document Code:
A
Abstract:
(+)nopinone was synthesized through selective oxidation of (-)βpinene, and the oxidation behavior of βpinene under different oxidants and solvents system were examined. Effects of the molar ratios of βpinene/KMnO4 and H2SO4/KMnO4, types of solvents, reaction temperature and time on the conversion of βpinene and selectivity of (+)nopinone were investigated. The results showed that the suitable oxidation conditions of (-)βpinene into (+)nopinone were as follows: βpinene/KMnO4 molar ratio 1∶3, H2SO4/KMnO4 molar ratio 0.054∶1, acetone was used as the solvent, reaction temperature 15—25 ℃, and reaction time 5 h. The conversion of βpinene, selectivity of oxidation, yield of (+)nopinone, specific rotation and purity of obtained product were 94.15 %, 89.19 %, 83.97 %, [α]18D+33.86°(c 1.01, CHCl3), and 95.29 %, respectively. The structure of (+)nopinone was determined by IR, 1H NMR, 13C NMR and GCMS spectra.

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Last Update: 2010-05-14