【作者】 苗楠楠；

【导师】 马英丽；

【作者基本信息】 黑龙江中医药大学 ， 中药学， 2006， 硕士

【摘要】 金雀异黄素（5,7,4′—三羟基异黄酮）是大豆异黄酮的主要成分,关于它的活性研究正日益深入。据报道,它的生物活性高于大豆异黄酮,其化学结构和相对分子量与雌二醇相似,能与其竞争雌激素受体,故有雌激素性质,可降低女性雌激素相关肿瘤的发病率,预防绝经后妇女因雌激素水平下降而导致的疾病,如心血管疾病和骨质疏松症等。 目前金雀异黄素主要来自大豆提取物,但因大豆中的含量极低,故产品成本较高。而随着金雀异黄素的多方面及较高的生物活性的逐渐发现以及应用研究的不断扩大和深入,加之全球对金雀异黄素的需求量迅速增长。迫切的需要用人工合成的方法获取它以满足研究和应用的需要。 本研究首先以间苯三酚,对羟基苯乙酸为原料,在催化剂作用下,经过Friedel-Crafts酰基化反应制得了中间体脱氧安息香;中间体再经亚甲基的甲醛化、脱水环合反应合成金雀异黄素。所得产物经IR、HPLC检测,并与标准品对照,确定在反应中合成了目标产物金雀异黄素。在此基础上,采用均匀试验设计法,对合成反应中涉及的主要影响因素进行了考察,所得试验结果经过SAS统计软件分析,采用逐步回归的方法建立模型。最终确定:（1）中间体脱氧安息香合成工艺优化条件为:反应温度-15℃,反映时间8h,加入三氟化硼乙醚2.8mol,其平均收率为66.4%。（2）金雀异黄素合成工艺优化条件为:反应温度为20℃,反映时间为46min,加入三氟化硼乙醚6.5mol,DMF0.06mol,Pcl₅2mol。经验证实验,在此工艺优化条件下金雀异黄素平均收率为71.60%。合成产物并用IR、HPLC、和¹H-NMR方法进行了鉴定。 本研究通过对金雀异黄素的化学合成、合成工艺优化研究,为金雀异黄素的后续研究（生物活性、新药研究等）奠定了良好的基础。更多还原

【Abstract】 Genistein is the main composition of the Soybean Isoflavone.It is deep about the study of its activity.It’s reported that its acitivity is higher than the Soybean Isoflavone.It is similar to its chemistry structure and molecular weight with Estradiol.It can compete the ER with Estradiol.So it has the property of female hormone.It can lower the outbreak rate of the tumor which is related to the level of the female hormone.Women are easy to get disease after the menopause .Such as the Cardiovascular disease and the bone soft disease. Genistein is mainly extracted from the Soybean currently. But now the method has many drawbacks.The content in the soybean is low.It is difficult to extracted from the soybean. Genistein is used in many aspects.So we want to have it across the synthesis. We synthesized the Genistein and we found the best way to obtain it in this experiment.The research is divided into two steps.Firstly we made Phloroglucinol and p-Hydroxyphenylacetic acid as the material.We got the Deoxybenzoins after the reaction of Friedel-Craftes.Secondly Genistein was synthesized in the presence of catalyst.Based on it,the research used uniform design to study the factors involved in the synthesis of Genistein.With SAS software the experiment result was used to build a proper model by stepwise regression.And then,the optimum processing condition was found.The first step:Reaction Temperature =-15℃,Reaction Time =8h,BF₃.Et₂O =2.8mmol.The second step: Reaction Temperature =20℃, Reaction Time =46min, BF₃·Et₂O =6.5mol,DMF =0.06mol,Pcl₅=2mmol. Under such processing condition,the yield reached 67.07%;71.60%.The craft of experiment has many advantages,such as the high yield,short reaction time, easy to get the material, low cost,scientific and reasonable craft,be suitable to the industrialproduction.更多还原