應用麥可加成反應來合成4, 6-二苯-1氫-萉-1-酮和4, 6-二苯-2氫-吡喃羧酸酯

Abstract

科學家們從許多不同的生物體中分離出許多具有生物活性的天然物，而其中有些分子具有萉酮及吡喃等特定結構。 本論文分為兩個部分，皆是透過二苯丙炔酮作為起始骨架，進行特定結構分子的合成，第一部分，先回顧這幾年來此一分子的性質及功用，研究及合成，是探討藉由1-萘酚與二苯丙炔酮進行一連串的合成過程以合成萉酮這一類的植物抗菌素，反應過程中透過三氟化硼(Boron trifluoride diethyl etherate，簡稱BF3)進行酸催化進行麥可加成反應，以合成萉酮化合物。 第二部分是探討藉由丙二酸酯與二苯丙炔酮進行一連串的合成過程，反應過程藉由路易斯鹼氫氧化鈉催化二乙基丙二酸酯先形成烯醇，再藉由麥可加成反應對三鍵炔類進行加成，先形成丙二烯(allene)，最終得到一高產率的吡喃酮化合物。Scientists have isolated many occurring natural substances from many different organisms, and some of them have specific structure such as pyrone and phenalene.

This thesis covers the combination of two separate works. The two parts both synthesized by the diphenylpropynone as the original skeleton. Among them, the first work refers to some references about the natures, functions of this molecule, and some researches and synthesis over the past few years. To explore how to synthesize this kind of molecule by series of processes, we were carried out with 1-naphthol and diphenylpropynone which is a kind of novel phytoalexins. The Lewis acid (boron trifluoride diethyl etherate (BF3)) catalyzed Michael addition reaction to synthesize phenalenone compounds during this reaction.

The second part is to explore series of synthetic processes by the combination of diethylmalonate and diphenylpropynone. Sodium hydroxide as a Lewis base catalyzed malonate to form enolate, involving the addition of alkyne to produce allene. At last, we got the pyrone compounds in a high yield.