交錯共軛α-酯基烯酮-醛化合物與氮-雜環碳烯之反應研究

Studies on the Reaction of the Cross-Conjugated α-Carbalkoxy Enone-Aldehydes in NHC-Mediated

黃美珠(Mei-Chu Huang)

指導教授 ： 許岱欣

國立中正大學/理學院/化學暨生物化學系/碩士(2012年)

摘要

本論文中，我們研究利用氮-雜環碳烯(NHC)催化之分子內Stetter反應建構螺環化合物。本研究使用的基質為交叉共軛之α-酯類烯酮化合物。交錯共軛之α-甲基酯類-β-(4-羰丁基)環己烯酮在NHC條件下可生成螺環[4.5]癸烷-1,7-二酮化合物，產率為93-96%。在3-羰丙基及5-羰戊基側鍊的環己烯酮例子中，於相同條件下會得到benzoin及氧化酯化反應之產物。然而，在4-羰丙基及5-羰戊基側鍊的環戊烯酮例子中，只能得到分子內aldol反應之產物。

關鍵字

氮-雜環碳烯

並列摘要

In this thesis we have studies N-heterocyclic carbine (NHC)-catalyzed intramolecular Stetter reaction to construct spiro compounds. The cross-conjugated α-carbalkoxyenones were used as substrates in the studied. Treatment of the cross-conjugated α-carbmethoxy-β-(4-oxobutyl)cyclohenones with NHC produced spiro[4.5]decane-1,7-diones in 93-96% yields. With 3-oxopropyl and 5-oxopentyl tether in cyclohexenones, the benzoin and oxidative esterification products were obtained under the same conditions. In the case of cyclopentenones with 4-oxobutyl and 5-oxopentyl side chains, however, only gave the intramolecular adol products.

並列關鍵字

N-heterocyclic carbene

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