化学学报 ›› 1990, Vol. 48 ›› Issue (11): 1113-1119. 上一篇    下一篇

研究论文

β-大马烯酮和β-大马酮的光化学合成

吴国生;胡军;吴碧琪;陈兆斌;王银章   

  1. 中国科学院上海有机化学研究所;山西大学化学系
  • 发布日期:1990-11-15

Photochemical syntheses of β-damascenone and β-damascenone

WU GUOSHENG;HU JUN;WU BIQI;CHEN ZHAOBIN;WANG YINZHANG   

  • Published:1990-11-15

从同一个中间体合成β-大马烯酮(1)和β大马酮(2), 烯丙基β-环香叶醇的光氧化得双环氧化合物3.3的羰基用邻硝基苯基乙二醇保护, 还原, 光化学去保护和脱水得2,3的酸催化开环, 保护选择还原和光化学去保护得1. 首次观察到末端双键在光氧化时的环氧化。

关键词: 光化学反应, 红外分光光度法, 光氧化, 硝基苯 P, 质子磁共振谱法, 达马烷, 酮, 环己二烯 P, 环己烯 P, 烯酮

b-Damascenone (I) and b-damascone (II) were synthesized from the same intermediate, the bisepoxide III, derived from the photooxidn. of allylic b-cyclogeraniol. Protection of the carbonyl group of III with o-nitrophenyl glycol, reduction, photodeprotection and dehydration gave II while I was obtained by means of acid catalytic ring-opening of the epoxy groups of III, protection, reduction and photodeprotection. It was the first time to observe epoxidn. of terminal double bond under photooxidn.

Key words: PHOTOCHEMICAL REACTION, INFRARED SPECTROPHOTOMETRY, PHOTOOXIDATION, NITROBENZENE P, PROTON MAGNETIC RESONANCE SPECTROMETRY, DAMMARAN, KETONE, CYCLOHEXADIENE P, CYCLOHEXENE P, KETENE

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