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치환 이중결합을 갖는 Isoxazoline의 산첨가 촉매 수소화 반응
김순옥,이은경,심정순 성신여자대학교기초과학연구소 1996 基礎科學硏究誌 Vol.15 No.-
Hydrogenolysis reaction of isoxazolines, empolying the Lindlar catalyst and acid additive, was investigated. Isoxazoline alcohols 1,2 were synthesized by the [3+2] cycloaddition reaction of hydroxyolefin with nitrile oxides generated from nonylaldehyde oxime and benzaldehyde oxime, using the Lee's method. Compounds 1,2 were then oxidized to isoxazoline aledhydes 3,4 by swern's method. Isoxazolines 5a-5j containing C-C double bond were obtained by the Witting reactions of isoxazolines 3,4 with phosphorances generated from phosphonium salt. The Lindlar catalyst and mixture of acetic acid and boric acid as additives were used for the effective hyerogenoysis of isoxazolines having phenyl group and octyl group at the carbon 3-position. Isoxazolines having octy1 group, 5f-5j could be hydrogenolyzed without reduction of double bonds, to give a good yield(69.55%-87%) of β-hydroxy ketone 6f-6j by the use of the Lindlar catalyst and 3.5:1.5 mixture of acetic acid and boric acid. From this study, we have shown that the present method of hydregenolysis provides useful means for the conversion of isoxazolines contaning double donds into β-hydroxy ketones, keeping the double bond intact. But, in case of isoxazolines having phenyl group at the earbon 3-position, the conversion was slow and thd yields were low.