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    高師機構典藏 NKNUIR > 理學院 > 化學系 > 博碩士論文 >  Item 987654321/15377
    Please use this identifier to cite or link to this item: http://ir.nknu.edu.tw/ir/handle/987654321/15377


    題名: 1,1’-雙薁烷基取代掌性輔助劑之合成、性質及應用研究
    Authors: 洪志熙
    貢獻者: 陳阿煌
    Arh-Hwang Chen
    Keywords: ;掌性輔助劑
    azulene
    Date: 2002-08-05
    Issue Date: 2011-05-30 16:54:14 (UTC+8)
    Abstract: 在有機不對稱的領域中掌性輔助劑,一直被廣泛研究與矚目。掌性輔助劑除了本身的應用之外,亦可以由此而製得更具有效力、且更經濟的掌性催化劑。BINOL(1,1’-bi-2-naphthol)是目前化學界最著名的掌性輔助劑之一,在合成上的運用範圍很廣。
    本篇論文在研究掌性輔助劑1,1’-二(3-甲氧羰基-8-甲基-2-薁酚)之合成、性質及應用研究。我們以二環戊二烯為起始,合成薁環的骨架2-胺基-1,3-二羧酸乙酯(19),再進行Sandmeyer反應將胺基轉成氯基;再利用甲基鋰進行親核性反應,此反應產生二種不同的親核性結果,其中一種為甲基接在4-位置後,2-位置的氯掉下來,此一結果與文獻48上的資料不同,故進一步探討其反應結果及產物之間的光譜差異。
    最後為了合成最終產物(100),將化合物(97)中2-位置的氯基置換成甲氧基(化合物98),再將其換成羥基(化合物99),最後用氯化鐵偶合得到最終目標分子(100);最後看是否有無像BINOL那樣,具有掌性輔助劑的效果。
    Asymmertric catalysis has always been studied widely and is the focus in organic synthesis. The development of chiral is a key in the asymmertric catalysis. BINOL(1,1’-bi-2-naphthol) is known as one of the most useful chiral auxiliaries. It’s used extensively in asymmetric catalysis.
    We study the synthesis of chiral auxiliaries BIAZOL(1,1’-bi-2-azuol).
    Diethyl 2-aminoazulene-1,3-dicarboxylate(19) were synthesis from dicyclopentadiene. We found that the reaction of diethyl 2-chloroazulene-1,3-dicarboxylate(16) with methyl lithium gave ethyl 2-chloroazulene-4-
    methyl-1-carboxylate(97) and ethyl 4-methylazulene-1-carboxylate(97’).
    After getting methyl 2-methoxyl-4-methylazulene-1-carboxylate(98), we go further into synthesis of methyl 2-hydroxy-4-methylazulene-1-carboxylate(99). Finally, the compound(99) were oxidized to give the compound(100) by ferric chloride.
    Appears in Collections:[化學系] 博碩士論文

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