[[alternative]]Total synthesis of (4z,7z,10z,13z,16z)-ethyl nonadeca-4,7,10,13,16-pentaenoate (ENDP) precursor

碩士[[abstract]]魚油含有非常多種類的脂肪酸，其中最廣泛為人所知且最有益處即是Omega-3脂肪酸，Omega-3是人體所必需卻不能自體製造的必須脂肪酸，在臨床上Omega-3的生理作用為降低血脂肪和消炎…等，在預防因血液凝集產生的動脈硬化或心肌梗塞更具有明顯效果。 魚油中常見的主要脂肪酸結構如下圖，且依結構中雙鍵的數量可以分成三大類型：飽和、單元不飽和以及多元不飽和脂肪酸。 CH3(CH2)m(CH=CHCH2)n(CH2)oCOOH 當n=0時，此結構稱為飽和脂肪酸，n=1時，為單元不飽和脂肪酸，n=2~6為多元不飽和脂肪酸。目前有許多長碳鏈 (C14-C22) 不飽和脂肪酸，和少量的(C10和C12)單元不飽和脂肪酸陸陸續續從魚油中被確認並鑑定其結構。 本研究的目的是利用全合成方法，設計合成出十九碳五烯乙基酯（EE form）的前驅物，可用來檢測魚油中是否含有此類型Omega-3的多元不飽和脂肪酸分子。[[abstract]]The fatty acids derived from fish oils employ as of three principal types: saturated, monounsaturated, and polyunsaturated fatty acid. Among those fatty acids in the fish oil, Omega-3, polyunsaturated fatty acid has shown most health benefits. Most current research presents that the anti-inflammatory activities of long-chain Omega-3 fatty acids may transform their biological activities into clinical applications. Omega-3 molecules have been considered as essential fatty acids for the human body, but they can’t be produced by human’s biological metabolism. The sole method to get the Omega-3 is by ingestion pathway. The aim of the study is to determine the specific structure of the fatty acid in fish oil and health supplements which containing the substance[[tableofcontents]]目錄 中文摘要 I 英文摘要 II 圖表目錄 III 第一章 緒論………………………………………………………........1 1-1 魚油………………………………………………………........3 1-1-1 健康益處 …………………………………………..........6 1-1-2 攝取量和關注 ……………………………………........11 1-1-3 可能的危害 ………………………………………........13 1-2 脂肪酸………………………………………………………..15 1-2.1 脂肪酸的種類 …………………………………………..16 1-2.2 飽和脂肪與飽和脂肪酸 ………………………………17 1-2.3 不飽和脂肪酸…………………………………………..20 1-2.3.1 ω-3脂肪酸………………………………………..22 1-3 合成方法的探討……………………………………………..23 第二章 結果與討論…………………………………………………..35 2-1 合成策略研究………………………………………………...35 2-2 研究結果與討論………………………………………….......44 第三章 實驗與儀器………………………………………………......63 3-1 儀器操作與測試方法 ……………………………………….63 3-2 溶劑的乾燥 ………………………………………………….75 3-3 反應條件及實驗步驟………………………………………...77 第四章 總結……………………………………………….………….79 第五章 光譜..........................................................................................81 第六章 參考資料..................................................................................93 Scheme 1 …………………………………………………………….......3 Scheme 2……………………………………………………………....... 4 Scheme 3……………………………………………………………....... 5 Scheme 4……………………………………………………………....... 5 Scheme 5 …………………………………………………………….......8 Scheme 6……………………………………………………………....... 9 Scheme 7 …………………………………………………………….....11 Scheme 8 …………………………………………………………….....15 Scheme 9 …………………………………………………………….....17 Scheme 10……………………………………………………………... 20 Scheme 11……………………………………………………………... 22 Scheme 12…………………………………………….………………...24 Scheme 13 ……………………………………………………………...24 Scheme 14 ……………………………………………………………...25 Scheme 15……………………………………………………………... 25 Scheme 16……………………………………………………………... 26 Scheme 17 ……………………………………………………………...26 Scheme 18 ……………………………………………………………...27 Scheme 19……………………………………………………………... 27 Scheme 20……………………………………………………………... 28 Scheme 21 ……………………………………………………………...28 Scheme 22……………………………………………………………... 29 Scheme 23 ……………………………………………………………...29 Scheme 24 ……………………………………………….……………..30 Scheme 25 ……………………………………………….……………..33 Scheme 26……………………………………………………………... 35 Scheme 27 ……………………………………………………………...36 Scheme 28 ……………………………………………………………...37 Scheme 29 ……………………………………………………………...37 Scheme 30……………………………………………………………... 38 Scheme 31 ……………………………………………………………...38 Scheme 32 ……………………………………………………………...40 Scheme 33 ……………………………………………………………...40 Scheme 34 ……………………………………………………………...41 Scheme 35 ……………………………………………………………...42 Scheme 36 ……………………………………………………………...44 Scheme 37 ……………………………………………………………...44 Scheme 38……………………………………………………………... 45 Scheme 39……………………………………………………………... 46 Scheme 40……………………………………………………………... 46 Scheme 41 ……………………………………………………………...47 Scheme 42 ……………………………………………………………...48 Scheme 43 ……………………………………………………………...48 Scheme 44 ……………………………………………………………...49 Scheme 45 ……………………………………………………………...49 Scheme 46 ……………………………………………………………...50 Scheme 47 ……………………………………………………………...51 Scheme 48 ……………………………………………………………...56 Scheme 49 ……………………………………………………………...56 Scheme 50 ……………………………………………………………...57 Scheme 51 ……………………………………………………………...57 Scheme 52 ……………………………………………………………...58 Scheme 53 ……………………………………………………………...59 Scheme 54 ……………………………………………………………...59 Scheme 55 ……………………………………………………………...60 Scheme 56 ……………………………………………………………...61 Scheme 57……………………………………………………………... 61 Scheme 58……………………………………………………………... 79 Scheme 59……………………………………………………………... 80 Table 1…………………………………………………………………..52 Table 2…………………………………………………………………..54 Table 3…………………………………………………………………..55[[note]]學號: 601160509, 學年度: 10