利用噁唑烷酮稠合?環丙烷之開環反應合成氟化纈胺酸

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溫啟勝(Chi-Sheng Wen) 查詢紙本館藏

畢業系所

化學學系

論文名稱

利用噁唑烷酮稠合?環丙烷之開環反應合成氟化纈胺酸

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至系統瀏覽論文 (2030-1-1以後開放)

摘要(中)

分子中引入氟可以改變化合物的物理與化學性質，例如疏水性、反應性、酸鹼性等，這些改變可使蛋白質與胜?有更多的利用性。同時氟化合物也具有作為正子造影劑的潛力，而放射性核種具有半衰期，於適當時機接上氟相當重要。本篇論文利用 D–酒石酸衍生物噁唑烷酮稠合?環丙烷來建立α 碳與 β碳的立體中心且有良好的立體選擇性，並經過一系列官能基的轉換使其於最後階段進行氟取代反應，合成氟化胺基酸。

摘要(英)

Incorporating fluorine into molecules can significantly alter their physical and chemical properties, such as hydrophobicity, reactivity, and acidity/basicity. These modifications enhance the versatility of proteins and peptides. Additionally, fluorinated compounds hold great potential as positron emission tomography (PET) imaging agents. Given the radioactive nature of fluorine isotopes and their limited half-time, introducing fluorine at the optimal stage is crucial. This study employs D-tartaric acid-derived oxazolidinone fused with aziridine to construct stereogenic centers at the α- and β-carbons with excellent stereoselectivity. Through a series of functional group transformations, the fluorination reaction is carried out in the final step, enabling the synthesis of fluorinated amino acids.

關鍵字(中)

★ 噁唑烷酮
★ ?環丙烷
★ 氟化纈胺酸

關鍵字(英)

論文目次

目錄
中文摘要 .................................................................................................. i
Abstract ................................................................................................... ii
目錄 ........................................................................................................iii
流程圖目錄 ............................................................................................. v
圖目錄 ................................................................................................... vii
反應式目錄 .......................................................................................... viii
表目錄 .................................................................................................... ix
附圖目錄 ................................................................................................. x
第一章緒論 ........................................................................................ 1
1-1 氟化胺基酸的介紹 ................................................................. 1
1-2 氟化胺基酸於正子造影應用與優勢...................................... 2
1-3 本實驗室對噁唑烷酮稠合?環丙烷進行氟開環反應之研究
4
1-4 研究動機 ................................................................................ 6
第二章結果與討論 ............................................................................... 8
2-1 氟化纈胺酸之逆合成分析 ....................................................... 8
2-2 合成 γ-氟化纈胺酸前驅物 ...................................................... 9
2-3 合成 β-氟化纈胺酸前驅物.................................................... 24
2-4 氟取代反應條件優化 ............................................................. 27
iv
第三章結論 ......................................................................................... 30
第四章實驗部分 ................................................................................. 31
4-1 實驗藥品及試藥 ..................................................................... 31
4-2 實驗器材與儀器 ..................................................................... 32
4-3 實驗步驟與光譜資訊 ............................................................. 33
第五章參考資料 ................................................................................. 82

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指導教授

侯敦仁

審核日期

2025-1-21

推文