研究生: |
黃正維 Huang, Jheng-Wei |
---|---|
論文名稱: |
經由Sulfa-Michael/Amino-cyclization/Acetalization非鏡像選擇性合成外消旋呋喃[2,3-e][1,4]噻嗪酮架構 Diastereoselective Synthesis of (±)-Furo[2,3-e][1,4] thiazinone scaffold via Sulfa-Michael/Amino-cyclization / acetalization |
指導教授: |
陳焜銘
Chen, Kwun-Min |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2018 |
畢業學年度: | 106 |
語文別: | 中文 |
論文頁數: | 93 |
中文關鍵詞: | 硫麥克加成反應 、胺環化反應 、縮醛反應 、呋喃噻嗪酮 |
英文關鍵詞: | Sulfa-Michael addition, amino-cyclization, acetalization |
DOI URL: | http://doi.org/10.6345/THE.NTNU.DC.049.2018.B05 |
論文種類: | 學術論文 |
相關次數: | 點閱:115 下載:6 |
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中文摘要
本文利用有機分子進行有機反應,發展具有高非鏡像選擇性之官能基的呋喃噻嗪酮結構。本實驗利用1,3-茚滿二酮 (三氟甲基)與2-胺基苯硫酚為起始物,在沒有催化劑的條件下,進行Sulfa-Michael/amino-cyclization/acetalization反應,得到多取代的呋喃[2,3,e][1,4]噻嗪酮結構,並同時建立三個四級碳及四個立體中心,具有傑出的產率(高達95%)及優異的非鏡像選擇性(高達 >20:1)。此外,也經由單晶繞射X-ray確認其產物的相對立體組態;也期許本實驗可應用在天然物合成及相關生物應用方面。
Abstract
In this thesis, organic molecules were used for organic reactions to develop furothiazinone structures with diastereoselective functionalized groups. In this experiment, Sulfa-Michael/amino-cyclization/acetalization reaction was performed by using 1,3-indanedione (trifluoromethyl) and 2-aminothiophenol as the initial starting materials in the absence of a catalyst. Multi-substituted furo[2,3,e][1,4]thiazinone structure, and the simultaneous establishment of three quaternary carbons and four stereocenters, with excellent yields (up to 95%) and diastereoselectivities (up to >20:1). In addition, the corresponding relative three-dimensional configuration of the product was also confirmed via single crystal diffraction X-ray; it is also expected that this experiment can be applied in the synthesis of natural products and related biological applications.
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