Facile Syntheses of 3-Isopentenyl Flavone and 3-Geranyl Flavone  

作　　者：HUANG Chu-sheng SHI Jian-cheng LIU Hong-xing CHEN Qian DUAN Hong-xia 

机构地区：[1]College of Chemistry and Life Sciences, Guangxi Teachers Education University, Nanning 530001, 1~ R. China," [2]Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, P. R. China

出　　处：《Chemical Research in Chinese Universities》2012年第6期994-998,共5页高等学校化学研究（英文版）

基　　金：Supported by the National Natural Science Foundation of China(No.20062001);the Natural Science Foundation of Guangxi Zhuang Autonomous Region,China(Nos.0991009 and 0447036)

摘　　要：Although there was a strong steric effect,isopentenyl and geranyl moieties were successfully introduced into C3 position in flavone skeleton so as to synthesize the 3-isopentenyl flavone and 3-geranyl flavone under two cyclization conditions（AcOH/HCl and concentrated H 2 SO 4 /MeOH） in this report.It was found that the optimum cyclization conditions for 3-isopentenyl flavone and 3-geranyl flavone were,respectively,AcOH/HCl and H 2 SO 4 /MeOH.Furthermore,the donating electron ability is in the sequence 3-geranyl flavone3-isopentenyl flavone according to the density functional theory（DFT） calculations,suggesting the longer alkyl chain at 3-position would be more favorable for enhancing the donating electron ability.The present synthetic routes might reveal potential applicability in our continued studies on the total syntheses of other natural 3-alkyl flavonoids.Although there was a strong steric effect,isopentenyl and geranyl moieties were successfully introduced into C3 position in flavone skeleton so as to synthesize the 3-isopentenyl flavone and 3-geranyl flavone under two cyclization conditions（AcOH/HCl and concentrated H 2 SO 4 /MeOH） in this report.It was found that the optimum cyclization conditions for 3-isopentenyl flavone and 3-geranyl flavone were,respectively,AcOH/HCl and H 2 SO 4 /MeOH.Furthermore,the donating electron ability is in the sequence 3-geranyl flavone3-isopentenyl flavone according to the density functional theory（DFT） calculations,suggesting the longer alkyl chain at 3-position would be more favorable for enhancing the donating electron ability.The present synthetic routes might reveal potential applicability in our continued studies on the total syntheses of other natural 3-alkyl flavonoids.

关 键 词：3-Isopentenyl flavone 3-Geranyl flavone 3-Alkyl flavonoid 

分 类 号：O629[理学—有机化学] TQ463.4[理学—化学]