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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 劉緒宗 | zh_TW |
| dc.contributor.advisor | Shiuh-Tzung Liu | en |
| dc.contributor.author | 王昱閔 | zh_TW |
| dc.contributor.author | Yu-Min Wang | en |
| dc.date.accessioned | 2024-12-24T16:10:17Z | - |
| dc.date.available | 2024-12-25 | - |
| dc.date.copyright | 2024-12-24 | - |
| dc.date.issued | 2024 | - |
| dc.date.submitted | 2024-12-16 | - |
| dc.identifier.citation | 1. Maitland, P.; Mills, W. H. Experimental Demonstration of the Allene Asymmetry. Nature 1935, 135, 994-994.
2. Yu, S.; Ma, S. Allenes in catalytic asymmetric synthesis and natural product syntheses. Angew. Chem., Int. Ed. Engl. 2012, 51, 3074-3112. 3. Yoshida, M.; Shoji, Y.; Shishido, K. Enantioselective formal total synthesis of aplysin utilizing a palladium-catalyzed addition of an arylboronic acid to an allenic alcohol—Eschenmoser/Claisen rearrangement. Tetrahedron 2010, 66, 5053-5058. 4. Liu, Z.; Wasmuth, A. S.; Nelson, S. G. Au(I)-Catalyzed Annulation of Enantioenriched Allenes in the Enantioselective Total Synthesis of (−)-Rhazinilam. J. Am. Chem. Soc. 2006, 128, 10352-10353. 5. Alonso, J. M.; Quirós, M. T.; Muñoz, M. P. Chirality transfer in metal-catalysed intermolecular addition reactions involving allenes. Org. Chem. Front. 2016, 3, 1186-1204. 6. Rivera-Fuentes, P.; Diederich, F. Allenes in molecular materials. Angew. Chem., Int. Ed. Engl. 2012, 51, 2818-2828. 7. Hoffmann-Roder, A.; Krause, N. Synthesis and properties of allenic natural products and pharmaceuticals. Angew. Chem., Int. Ed. Engl. 2004, 43, 1196-1216. 8. Burton, B. S.; von Pechmann, H. Ueber die Einwirkung von Chlorphosphor auf Acetondicarbonsäureäther. Ber. Dtsch. Chem. Ges. 2006, 20, 145-149. 9. Jacobs, T. L.; Akawie, R.; Cooper, R. G. Rearrangements Involving 1-Pentyne, 2-Pentyne and 1,2-Pentadiene1. J. Am. Chem. Soc. 1951, 73, 1273-1276. 10. Fenández, I.; Monterde, M. I.; Plumet, J. On the base-induced isomerization of cyclic propargylamides to cyclic allenamides. Tetrahedron Lett. 2005, 46, 6029-6031. 11. Fu, L.; Greßies, S.; Chen, P.; Liu, G. Recent Advances and Perspectives in Transition Metal‐Catalyzed 1,4‐Functionalizations of Unactivated 1,3‐Enynes for the Synthesis of Allenes. Chin. J. Chem. 2019, 38, 91-100. 12. Li, Y.; Bao, H. Radical transformations for allene synthesis. Chem. Sci. J. 2022, 13, 8491-8506. 13. Zhang, W.; Xu, H.; Xu, H.; Tang, W. 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Copper-catalyzed dimerization fragmentation cyclization reactions of (E)-1-en-4-yn-3-ols as a versatile approach for the synthesis of multisubstituted 1H-cyclopenta[b]naphthalenes. Org. Biomol. Chem. 2011, 9, 7461-7467. | - |
| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/96286 | - |
| dc.description.abstract | 聯烯由於結構的特殊性，具獨特的化學性質，常被用於有機合成上，在天然物、藥物與一些功能性材料上也有廣泛的應用性。本研究成功使用 (2-丙炔氧基)烯炔醚1在鈀金屬的催化下合成3-聯烯基-4-亞甲基四氫呋喃2；進而針對2的反應性做進一步探討。若使用碘分子與三取代聯烯2 (R3 = Ph) 進行反應，其會進行分子內一連串親電性加成與取代反應，生成三環分子6。而若將雙取代聯烯2 (R3 = H) 置於溝呂木－赫克反應條件下，則可以通過連續的遷移插入反應得到四氫異苯並呋喃4；此結構可進一步在2,3-二氯-5,6-二氰對苯醌 (DDQ) 的幫助下進行脫氫反應，得到二氫異苯並呋喃5。本研究拓展了零價鈀金屬對炔基的活化，提供一種嶄新的方法合成多取代聯烯2，也揭示了利用2產生三環化合物 6 和四氫異苯並呋喃 4 的新合成方法。 | zh_TW |
| dc.description.abstract | Due to the unique structural characteristics, allenes exhibit distinct chemical properties, allowing them to be invaluable in organic synthesis typically for natural products, pharmaceuticals, and functional materials. In this research, we have developed a new methodology to construct 3-allenyl-4-methylenetetrahydrofurans 2 from Pd-catalyzed cyclization of (Z)-5-(prop-2-yn-1-yloxy)pent-3-en-1-yne 1 through the vinyl-Pd intermediate I. Reactivity of 2 was further investigated. Treatment of the trisubstituted allene (2, R3 = Ph) with iodine caused a cascade cyclization to yield a spiral 5-5-5-tricyclic ring 6. On the other hand, reaction of the disubstituted allene (2, R3 = H) with aryl iodide proceeded a cascade insertion to produce tetrahydroisobenzofurans 4 under Heck reaction conditions. The oxidation of 4 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) resulted in the formation of 1,3-dihydroisobenzofuran 5. This research extends a palladium catalyzed activation of alkynyl groups for the synthesis of multi-substituted allenyltetrahydrofurans 2 and reveals new reactivity of 2 leading to 5-5-5-tricyclic rings 6 and tetrahydroisobenzofurans 4. | en |
| dc.description.provenance | Submitted by admin ntu (admin@lib.ntu.edu.tw) on 2024-12-24T16:10:17Z No. of bitstreams: 0 | en |
| dc.description.provenance | Made available in DSpace on 2024-12-24T16:10:17Z (GMT). No. of bitstreams: 0 | en |
| dc.description.tableofcontents | 摘要 i
ABSTRACT ii 目次 iii 附圖目次 v 附表目次 vi 流程目次 vii 第一章 緒論 1 1.1 聯烯的應用與合成策略 1 1.2 過渡金屬與不飽和鍵的反應性 4 1.3 1,4,3-烯炔醇衍生物的相關反應研究 6 1.4 研究動機與目的 8 第二章 3-聯烯基-4-亞甲基四氫呋喃的合成 9 2.1 起始物 (2-丙炔氧基)烯炔醚的製備 9 2.2 反應測試與結構鑑定 10 2.3 反應條件最佳化 14 2.4 聯烯基四氫呋喃的反應物容忍度測試 17 2.5 生成聯烯基四氫呋喃的反應機制探討 22 第三章 3-聯烯基-4-亞甲基四氫呋喃的合成應用 24 3.1 溝呂木－赫克反應於聯烯基四氫呋喃的合成應用 24 3.1.1 反應測試與結構鑑定 25 3.1.2 反應條件最佳化 27 3.1.3 四氫異苯並呋喃的反應物容忍度測試 29 3.1.4 反應機制探討 32 3.2 親電加成反應於聯烯基四氫呋喃的應用 34 3.2.1 初步反應測試與結構鑑定 35 3.2.2 反應條件最佳化 37 3.2.3 親電加成反應的反應物容忍度測試 39 3.2.4 反應機制討論 41 第四章 結論 43 第五章 實驗部分 44 5.1 實驗儀器與試劑 44 5.2 實驗步驟 45 5.2.1 查爾酮S3的標準合成步驟： 45 5.2.2 1,4,3-烯炔醇S4的標準合成步驟： 45 5.2.3 (2-丙炔氧基)烯炔醚1的標準合成步驟： 46 5.2.4 (2-丙炔氧基)烯炔醚1的去矽基化 46 5.2.5 3-聯烯基-4-亞甲基四氫呋喃2的合成 47 5.2.6 四氫異苯並呋喃4的合成 47 5.2.7 1,3-二氫異苯並呋喃5c的合成 48 5.2.8 三環分子6的合成 48 5.3 實驗數據 49 (2-丙炔氧基)烯炔醚1 49 3-聯烯基-4-亞甲基四氫呋喃2 59 氫芳基化產物3aa 74 四氫異苯並呋喃4 75 1,3-二氫異苯並呋喃5 83 三環分子6 86 第六章 參考資料 90 附錄一 (2-丙炔氧基)烯炔醚的合成 100 附錄二 化合物之光譜資料 103 附錄三 化合物之晶體資料 176 | - |
| dc.language.iso | zh_TW | - |
| dc.subject | 聯烯基衍生化 | zh_TW |
| dc.subject | (Z)-戊-2-烯-4-炔-1-醇衍生物 | zh_TW |
| dc.subject | 雙取代聯烯基雜環化合物 | zh_TW |
| dc.subject | 三取代聯烯基雜環化合物 | zh_TW |
| dc.subject | allene derivatizations | en |
| dc.subject | trisubstituted allenylheterocycles | en |
| dc.subject | disubstituted allenylheterocycles | en |
| dc.subject | (Z)-pent-2-en-4-yn-1-ol derivatives | en |
| dc.title | 3-聯烯基-4-亞甲基四氫呋喃的合成與其衍生化 | zh_TW |
| dc.title | Synthesis of 3-Allenyl-4-methylenetetrahydrofurans and Their Synthetic Applications | en |
| dc.type | Thesis | - |
| dc.date.schoolyear | 113-1 | - |
| dc.description.degree | 碩士 | - |
| dc.contributor.oralexamcommittee | 蔡蘊明;詹益慈;侯敦仁 | zh_TW |
| dc.contributor.oralexamcommittee | Yeun-in Tsai;Yi-Tsu Chan;Duen-Ren Hou | en |
| dc.subject.keyword | 三取代聯烯基雜環化合物,雙取代聯烯基雜環化合物,(Z)-戊-2-烯-4-炔-1-醇衍生物,聯烯基衍生化, | zh_TW |
| dc.subject.keyword | trisubstituted allenylheterocycles,disubstituted allenylheterocycles,(Z)-pent-2-en-4-yn-1-ol derivatives,allene derivatizations, | en |
| dc.relation.page | 194 | - |
| dc.identifier.doi | 10.6342/NTU202404725 | - |
| dc.rights.note | 同意授權(全球公開) | - |
| dc.date.accepted | 2024-12-17 | - |
| dc.contributor.author-college | 理學院 | - |
| dc.contributor.author-dept | 化學系 | - |
| 顯示於系所單位： | 化學系 | |
文件中的檔案：
| 檔案 | 大小 | 格式 | |
|---|---|---|---|
| ntu-113-1.pdf | 12.84 MB | Adobe PDF | 檢視/開啟 |
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