甾体皂甙元解废弃物(r)-3-甲基-γ-丁酸内酯的合成反应研究.pdfVIP

摘要 甾体皂甙元是我国甾体化学工业的基本原料，我们小组近年来以资源化学和 绿色化学为发展的方向，发展了洁净的降解甾体皂甙元的方法，该方法不但对环 境友好，同时可将甾体皂甙元降解为甾体内酯、孕甾醇、孕甾烯酮和雄甾醇，并 可从降解废料中提取出副产物 (R)-4- 甲基- δ-戊酸内酯以及(R)-3-甲基- γ-丁 酸内酯。(R)-4-甲基- δ-戊酸内酯已投入多种天然产物的合成研究工作。然而， 由于我们组先前没有实现对(R)-3-甲基- γ-丁酸内酯的提取和积累，限制了它在 有机合成中的应用。本论文以提取(R)-3-甲基- γ-丁酸内酯为起点，利用其合成 一些有应用价值或潜在应用价值的有机小分子，并应用在香料Citralis Nitrile 合 成研究中。本论文的工作主要有以下几个部分： 1.提取手性(R)-3-甲基- γ-丁酸内酯。 2.以(R)-3-甲基- γ-丁酸内酯为原料，以86 %，91 %，90 %的收率分别合成 (R)-4-溴－3－甲基丁酸乙酯, (R)-4-苄氧基－3－甲基丁酸，以及(R)-4- 苄氧基－3－甲基丁酸苄酯。 3.将以上合成片段应用到Citralis Nitrile 的合成研究中。 关键词：(R)-3-甲基- γ-丁酸内酯， (R)-4-溴－3－甲基丁酸乙酯, (R)-4-苄氧 基－3－甲基丁酸，(R)-4-苄氧基－3－甲基丁酸苄酯，Citralis Nitrile ，合成； Abstract Steroidal sapogenins are valuable starting materials in the industry of steroid chemistry. During the development of the Green and Resource Chemistry, our group has invented an efficient and environmemt-friendly method to degrade steroidal sapogenins with hydrogen peroxide, and the optically pure (R)-5-methyl-tetrahydropyran-2-one and (R)-4-methyl-dihydrofuran-2(3H)-one can be obtained from the reaction of steroidal sapongenins’ degradation. (R)-5-methyl-tetrahydropyran-2-one as a new chiral source has been used in synthesis of natural compounds.The work to obtain the (R)-4-methyl-dihydrofuran-2(3H)-one didn’t finish in our group before which confined the application of (R)-4-methyl-dihydrofuran-2(3H)-one. My master dissertation work mainly focused on obtaining the (R)-4-methyl-dihydrofuran-2(3 H)-one at first,then converted it into several chiral reagents and used the chairal reagents for the synthesis of Citralis Nitrile，a commercial spice . This dissertation includes four par