基于槲皮素结构的氨基醌类化合物的合成

SYNTHESIS OF AMINO QUINONE COMPOUNDS BASED ON STRUCTURE OF QUERCETIN

以槲皮素为主要原料,分别和糠胺、吗啡啉和环己胺反应。在一定的碱性条件下槲皮素B环的两相邻羟基优先被氧化为邻醌,后者与胺类再通过迈克尔加成反应,6′位氢被氨基取代,制备了基于槲皮素结构的氨基醌类化合物。实验结果表明,在槲皮素和胺物质的量比为1∶1,乙醇为溶剂,pH=9.2的条件下,分别得到产物4-[(呋喃-2-甲基)-氨基]-5-(3,5,7-三羟基-4-氧-4H-苯并吡喃-2-基)-[1,2]苯醌,4-吗啉-4-基-5-(3,5,7-三羟基-4-氧-4H-苯并吡喃-2-基)-[1,2]苯醌和(Z)-2-(6-(环己亚氨基)-3-(环己氨基)-4-氧代环己烷-1,5-二烯-1-基)-3,5,7-三羟基-4H-苯并吡喃-4-酮。通过IR、UV、MS和~1H NMR对产物进行表征。

Quercetin appliedy as main raw material,reacted with furfurylamine,morpholine and cyclohexylamine respectively.Under certain alkaline conditions,the two adjacent hydroxyl groups of the quercetin B ring are preferentially oxidized to o-quinone,which is replaced by the amine by the Michael addition reaction and the 6＇-position hydrogen is replaced by the amino group.The amino quinone compounds based on quercetin structure were prepared.Experimental results showed that the products 4-（（furan-2-ylmenthyl）amino）-5-（3,5,7-trih-ydroxy-4-oxo-4H-chromen-2-yl）cyclohexa-3,5-diene-1,2-dione,4-morpholino-5-（3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl）cyc-lohexa-3,5-diene-1,2-dione and（Z）-2-（6-（cyclohexylamino）-3-（cyclohexylimino）-4-oxocyclohexa-1,5-dien-1-yl）-3,5,7-trihydroxy-4H-chromen-4-one are synthesized with the molar ratio of quercetin to amine 1∶1,the solvent ethanol and pH = 9.2.The products were characterized by IR,UV,MS and ~1H NMR.Under certain alkaline conditions,the two adjacent hydroxyl groups of the quercetin B ring are preferentially oxidized to o-quinone,which is replaced by the amine by the Michael addition reaction and the 6′-position hydrogen is replaced by the amino group.Under alkaline conditions,quercetin applied as main raw material,reacted with furfurylamine,morpholine and cyclohexylamine respectively.The results showed that the products 4-（（furan-2-ylmenthyl）amino）-5-（3,5,7-trih-ydroxy-4-oxo-4 Hchromen-2-yl）cyclohexa-3,5-diene-1,2-dione（b）,4-morpholino-5-（3,5,7-trihydroxy-4-oxo-4 Hchromen-2-yl）cyc-lohexa-3,5-diene-1,2-dione（c）and（Z）-2-（6-（cyclohexylamino）-3-（cyclohexylimino）-4-oxocyclohexa-1,5-dien-1-yl）-3,5,7-trihydroxy-4H-chromen-4-one（d）are synthesized with the molar ratio of quercetin to amine 1∶1,the solvent ethanol and pH=9.2.The products were characterized by IR,UV,MS and 1H NMR.