大黃酚之合成

Synthesis of Chrysophanol

劉昭成(Chao-Cheng Liu)

指導教授 ： 楊嘉喜

中原大學/理學院/化學研究所/碩士(2005年)

https://doi.org/10.6840/cycu200500520

摘要

大黃酚、大黃酸、大黃素、蘆薈大黃素及大黃素甲醚等蒽醌衍生物都是天然藥材大黃中的指標成份，要從天然藥材中單離這些指標成份，不僅繁複而且產率不高，考量其彼此間分子結構類似，因此若能以價格較低的起始物，精簡的合成步驟來合成上述五種指標成份，應有實際利用之價值。
本實驗開始的一系列反應如下，起始物為2,3-二甲基苯甲醚(2,3-Dimethylanisole)(I)，經高錳酸鉀(Potassium Permanganate)氧化形成3-甲氧基鄰苯二甲酸(3-Methoxyphthalic acid)(II)，再與醋酸酐(Acetic anhydride)反應，脫水形成 3-甲氧基鄰苯二甲酸酐(3-Methoxyphthalic anhydride)(III)。另一方面，將3-甲基苯甲醚(3-Methylanisole) (IV)與N-溴基琥珀醯亞胺(N-bromosuccinimide，NBS)反應形成4-溴-3-甲基苯甲醚(4-Bromo-3-Methylanisole)(V)。最後化合物III與V以三氯化鋁(AlCl3)為反應劑，進行二次Friedel-Crafts反應，形成大黃酚(1,8-二羥基-3-甲基-9,10-蒽醌 ) (1,8-dihydroxy-3-methyl -9,10-anthraquinone) (VI)，實驗結果證明可以成功合成上述反應。

關鍵字

蒽醌衍生物 ； 大黃酚 ； 指標成份

並列摘要

The derivatives of anthraquinones such as Chrysophanol, Rhein, Emodin, Aloe-emodin and Physicon are marker components of the natural herb Rhubarb. Current procedures to extract these single compounds from the herb are complex with very low yield. Considering the similar structures of these compounds, being able to synthesize these five compounds from cheaper starting materials in a few steps becomes very valuable for practical industrial applications.
In the first series of reactions, the starting material of this study is 2,3-Dimethylanisole (I), oxidizing to form 3-Methoxyphthalic acid (II) by Potassium Permanganate, reacting with acetic anhydride to give 3-Methoxyphthalic anhydride (III) by dehydration. In the other reaction, 3-Methylanisole (IV) reacts with N-bromosuccinimide (NBS) to form 4-Bromo-3-Methylanisole (V). Finally, Methoxyphthalic anhydride (III) reacts with 4-Bromo-3-Methylanisole (V) in the presence of AlCl3 through two Friedel-Crafts reactions to obtain the product 1,8-dihydroxy-3-methyl-9,10-anthraquinone (VI). The successive procedures are shown in this study.

並列關鍵字

chrysophanol ； marker components ； anthraquinone derivatives

參考文獻

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