(I)一鍋化反應合成吳茱萸次鹼及其類似物(II)新一代磷離子液體之合成及其化學穩定性之探討

(I) One-pot Synthesis of Rutaecarpine and Its Analogues (II) New Phosphonium Ionic Liquids with Much Improved Chemical Stability

沈孟真(Meng-Jane Shen)

指導教授 ： 朱延和

國立中正大學/理學院/化學暨生物化學系/碩士(2012年)

摘要

本論文共包含兩個研究題目，第一部份為具喹唑啉酮骨架的天然物及其衍生物的合成。從商業便宜的試劑與離子液體[b-3C-im][NTf2]經由一鍋化的過程，可以成功的建構出具有喹唑啉酮和β-咔啉架構的吳茱萸及其類似物。在這項研究中，證明離子液體作為離子溶劑可以用於天然物的合成。
第二部份為新一代磷離子液體的合成與穩定性的探討。本實驗室由較早期以tricyclohexylphosphine為起始物，另一端接上直鏈的烷基化合物，顯示其穩定性比市售的磷離子液體穩定，但在鹼性條件下會參與反應。本論文以tricyclohexylphosphine做為起始物，另一端接上具有支鏈的烷基化合物，在高溫高壓下，成功的合成出新一代磷離子液體，並且具有高度的穩定性。

關鍵字

吳茱萸 ； 磷離子液體

並列摘要

This thesis studies two different research projects. The first project aims at constructing quinazolinone based natural alkaloid – rutaecarpine. Starting with inexpensive commercial available reagents, rutaecarpine and its analogues, whose cores are quinazolinone and β carboline, were readily synthesized in ionic liquid, [b-3C-im][NTf2], via one pot chemical process. In this study, it is demonstrated the practical utility to use ionic liquid as solvent in natural product synthesis.
The second project deals with the work entitled “New
phosphonium ionic liquids with much improved chemical stability”. In previous studies, tricyclohexyl(butyl)phosphonium bromide (P-4C-Br) and tricyclohexyl(tetradecyl)phosphonium bromide (P-14C-Br) was synthesized and characterized, which revealed improved stability than commercially available phosphonium ionic liquid. However,
P-4C-Br and P-14C-Br are reactive under basic conditions. A new
room-temperature ionic liquid, tricyclohexyl(nonan-2-yl)phosphoniumbis((trifluoromethyl)sulfonyl)amide, developed in our laboratory
appears to be more stable under basic condition.

並列關鍵字

Rutaecarpine ； Phosphonium Ionic Liquid

參考文獻

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