2-甲基-7-羟基异黄酮及其糖苷类化合物的合成研究  

Efficient Synthesis of 2-Methyl-7-Hydroxyisoflavone and Its Isoflavonoid Glycosides

作　　者：汪秋安[1] 吴峥[1] 方伟琴[1] 吴汉[1] 

机构地区：[1]湖南大学化学化工学院,湖南长沙410082

出　　处：《湘潭大学自然科学学报》2009年第2期77-81,共5页Natural Science Journal of Xiangtan University

基　　金：湖南省"十一五"科技专项资助项目(No.2006NK1002)

摘　　要：以问苯二酚和苯乙酸为原料，通过Friedel—Craites酰化反应和碱性条件下的缩合反应．合成得到2-甲基-7-羟基异黄酮（化合物1），将1在VDMF：y月_：3：2的混合溶剂中，以K2C03为碱性缩合剂，四丁基溴化铵（TBAB）为相转移催化剂，分别与α-溴代乙酰葡萄糖、α-溴代乙酰半乳搪和α-溴代乙酰麦芽糖发生糖苷化反应，随后在氨水存在下发生脱乙酰基反应t合成得到了3种未见文献报道的2-甲基-7-O-βD-异黄酮苷化合物2～4．所合成的产物通过MS，1HNMR和IR等波谱方法进行了结构确证．该合成方法同其他异黄酮苷合成方法相比，具有反应条件温和、后处理简单、产率较高和立体选择性强的优点，具有较大的应用价值．Three novel 2-methylisoflavonoid -7-0- β-D -glycosides 2-4 were synthesized from 2-methyl-7- hydroxy isoflavone I with corresponding a-acetylglycosyl bromides by glyeosidation and deacetylation reac- tion. 1 was prepared by Friedel -Craftes acetylation and basic condensation reaction using 2,4-dihydroxy- benzene and phenylacetic acid as starting material. The synthetic procedure of glyeosidation was modified by using anhydrous K2CO2 in a solvent mixture of DMF/acetone （3 ： 2 V/V ） and TBAB as a phase transfer catalyst. The structures of all compounds synthesized were determined by MS, 1HNMR and IR spectra. Compared with the previously reported methods, the modified glyeosidation method has advantages of mild reaction condition, simple operation, high stereospecification and good yields, so it has considerable practi- cal value.

关 键 词：异黄酮类 2-甲基-7-羟基异黄酮 糖苷化 相转移催化 合成 

分 类 号：O625.4[理学—有机化学]