I. 經有機膦催化誘導4-亞芳基吡唑酮和5-亞芳基噻唑酮的β-醯化反應II. 鹼催化2-羥基亞胺葉立德與2-羥基亞芳基噻唑酮經由1,3-偶極體環化/分子內環化反應合成螺環𠳭酮[3,4-b]吡咯啶
| dc.contributor | 林文偉 | zh_TW |
| dc.contributor | Lin, Wen-Wei | en_US |
| dc.contributor.author | 陳永昌 | zh_TW |
| dc.contributor.author | Chen, Yung-Chang | en_US |
| dc.date.accessioned | 2022-06-08T02:42:08Z | |
| dc.date.available | 9999-12-31 | |
| dc.date.available | 2022-06-08T02:42:08Z | |
| dc.date.issued | 2021 | |
| dc.description.abstract | 第一部分：敘述實驗室設計使用α,β-不飽和共振系統的4-亞芳基吡唑酮和5-亞芳基噻唑酮以一鍋化反應中藉由非金屬有機膦催化反應對β位置進行親核共軛加成，接著藉由氧醯化/分子內環化反應形成中間體Phosphrous betaine 接著經由分子內重排反應，最終可以得到具有立體專一性並且產率高達90%以上β-碳醯化反應4-亞芳基吡唑酮以及5-亞芳基噻唑酮的產物。第二部分：經由設計開發出一種經由2-羥基亞胺葉立德與2-羥基亞芳基噻唑酮透過有機鹼催化反應1,3-偶極體環化加成反應以及進一步的連鎖反應建構出螺環𠳭酮[3,4-b]吡咯啶的方法，而最佳化結果顯示，可以在短時間內得到高達93％的產率。另外我們實驗室正在努力設計出不同取代基效應的螺環𠳭酮[3,4-b]吡咯啶以及不對稱合成的研究。 | zh_TW |
| dc.description.abstract | I. An efficient phosphine-catalyzed Beta-C-acylation methodology of pyrazolones and thiazolones arylidene were reported in thesis. Various bata acylated products were affordrd from the corresponding 4-arylidene pyrazolones and 5-arylidene thiazolones with acyl chlorides under organophosphane catalysis, resulting in excellent yields and specific stereoisomers. The reaction is believed to proceed via a tandem phospha-Michael addition/O-acylation/intramolecular betaine formation/acyl group rearrangement sequence. Furthermore, this methodology can also be applied in gram-scale with similar efficacy.II. An organobase-catalyzed diastereoselective synthesis of thiazolone spirochromeno[3,4-b]pyrrolidine were reported in the part II of this thesis. The optimized method provided the desired spirochromeno[3,4-b]pyrrolidines in good yield from the cascade 1,3-dipolar cycloaddition/lactonization of 2-hydroxyl azomethine ylide and 2-hydroxyarylidene thiazolone in a short reaction time. | en_US |
| dc.description.sponsorship | 化學系 | zh_TW |
| dc.identifier | 60842020S-39497 | |
| dc.identifier.uri | https://etds.lib.ntnu.edu.tw/thesis/detail/d83eab53b138ca517b23cc0d04e4a12e/ | |
| dc.identifier.uri | http://rportal.lib.ntnu.edu.tw/handle/20.500.12235/117218 | |
| dc.language | 中文 | |
| dc.subject | β-碳醯化反應 | zh_TW |
| dc.subject | 非金屬有機膦催化反應 | zh_TW |
| dc.subject | 立體專一性 | zh_TW |
| dc.subject | 一鍋化反應 | zh_TW |
| dc.subject | 4-亞芳基吡唑酮 | zh_TW |
| dc.subject | 5-亞芳基噻唑酮 | zh_TW |
| dc.subject | 螺環𠳭酮[3 | zh_TW |
| dc.subject | 4-b]吡咯啶 | zh_TW |
| dc.subject | 有機鹼催化反應 | zh_TW |
| dc.subject | 1 | zh_TW |
| dc.subject | 3-偶極體環化加成反應 | zh_TW |
| dc.subject | 連鎖反應 | zh_TW |
| dc.subject | 2-羥基亞胺葉立德 | zh_TW |
| dc.subject | 2-羥基亞芳基噻唑酮 | zh_TW |
| dc.subject | Beta-C-acylation | en_US |
| dc.subject | organophosphane catalysis | en_US |
| dc.subject | stereospecificity | en_US |
| dc.subject | one-pot reaction | en_US |
| dc.subject | 4-arylidene pyrazolones | en_US |
| dc.subject | 5-arylidene thiazolones | en_US |
| dc.subject | thiazolone spirochromeno[3 | en_US |
| dc.subject | 4-b]pyrrolidines | en_US |
| dc.subject | organobase-catalyzed | en_US |
| dc.subject | cascade 1 | en_US |
| dc.subject | 3-dipolar cycloaddition | en_US |
| dc.subject | lactonization | en_US |
| dc.subject | 2-hydroxyl azomethine ylides | en_US |
| dc.subject | 2-hydroxyarylidene thiazolones | en_US |
| dc.title | I. 經有機膦催化誘導4-亞芳基吡唑酮和5-亞芳基噻唑酮的β-醯化反應II. 鹼催化2-羥基亞胺葉立德與2-羥基亞芳基噻唑酮經由1,3-偶極體環化/分子內環化反應合成螺環𠳭酮[3,4-b]吡咯啶 | zh_TW |
| dc.title | I. Organophosphane-Catalyzed Direct β-Acylation of 4-Arylidene Pyrazolones and 5-Arylidene Thiazolones with Acyl ChloridesII. Base-Catalyzed Construction of Spirochromeno[3,4-b]pyrrolidines via 1,3-Dipolar Cycloaddition/Intramolecular Annulation of 2-Hydroxy Azomethine Ylides with 2-Hydroxyarylidene Thiazolones | en_US |
| dc.type | 學術論文 |