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姓名	阮氏英虹(NGUYEN THI ANH HONG)  查詢紙本館藏	畢業系所	化學學系
論文名稱	芳烴的無金屬直接乙酰氧基化和從(+)−脫氫樅胺全合成17−羥基曼陀羅B (Metal−Free, Direct Acetoxylation of Arenes and Total synthesis of 17−Hydroxymandarone B from (+)−Dehydroabietylamine)
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摘要(中)	芳烴的乙酰氧基化是重要的反應，也是化學中未滿足的需求。 我們報告了在三氟乙酸、乙酸和乙酸酐的無水環境下使用硝酸鹽進行的無金屬直接乙酰氧基化反應。 芳烴（31 個實例）的氧化電位（Eox，單位為 V vs SCE）低於苯（2.48 V），以良好的產率和區域選擇性被乙酰氧基化。我們 提出了一種逐步的單電子轉移機制。 樅烷二萜 (±)−17−Hydroxymandarone B (3) 的首次具有生物學意義的合成是從 (+)−脫氫樅胺實現的。 乙酰氧基化是簡單合成單乙酸酯 (7)、二乙酸酯 (4) 和三乙酸酯 (5) 的重要步驟。 這些化合物是 (±)−17−Hydroxymandarone B (3) 合成中的關鍵中間體。 在這個關鍵程序之後，精心控制的最終程序被開發出來，導致天然物的完成。
摘要(英)	Acetoxylation of arenes is important reaction and an unmet need in chemistry. We report a metal−free, direct acetoxylation reaction using nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid and acetic anhydride. Arenes (31 examples), with oxidation potentials (Eox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A stepwise, single electron−transfer mechanism is proposed. The first biologically significant synthesis of abietane diterpene (±)−17−Hydroxymandarone B (3) was achieved from (+)−Dehydroabietylamine. Acetoxylation is an important step for the simple synthesis of monoacetate (7), diacetate (4), and triacetate (5). These compounds are key intermediates in the synthesis of (±)−17−Hydroxymandarone B (3). Following this critical sequence, a meticulously controlled final sequence of events was developed that led to the completion of the product nature.
關鍵字(中)	★ 直接乙酰氧基化 ★ 17−羥基曼陀羅 B	關鍵字(英)	★ Direct Acetoxylation ★ 17−Hydroxymandarone B
論文目次	Chinese Abstract i English Abstract ii Acknowledgments iii Table of Contents iv List of Figures viii List of Tables ix List of Schemes x Explanation of Symbols xi Chapter I. Metal−Free, Direct Acetoxylation of Arenes 1 I-1. Introduction 1 I-2. Methodology 1 I-3. Resuts and discussions 3 I-4. Reaction mechanism 9 I-5. Natural compound synthesis application 11 I-6. Conclusion 12 I-7. Experimental Section 12 I.7.1. General information 12 I.7.2. Experimental procedures and data 13 References 27 Appendices 33 1H NMR of compound 2a (300 MHz, CDCl3) 34 13C{1H} NMR of compound 2a (75 MHz, CDCl3) 35 1H NMR of compound 2b (300 MHz, CDCl3) 36 13C{1H} NMR of compound 2b (75 MHz, CDCl3) 37 1H NMR of compound 2c (300 MHz, CDCl3) 38 13C{1H} NMR of compound 2c (75 MHz, CDCl3) 39 1H NMR of compound 2d (300 MHz, CDCl3) 40 13C{1H} NMR of compound 2d (75 MHz, CDCl3) 41 1H NMR of compound 2e (300 MHz, CDCl3) 42 13C{1H} NMR of compound 2e (75 MHz, CDCl3) 43 1H NMR of compound 2f (300 MHz, CDCl3) 44 13C{1H} NMR of compound 2f (75 MHz, CDCl3) 45 1H NMR of compound 2g (300 MHz, CDCl3) 46 13C{1H} NMR of compound 2g (75 MHz, CDCl3) 47 1H NMR of compound 2g’ (300 MHz, CDCl3) 48 13C{1H} NMR of compound 2g’ (75 MHz, CDCl3) 49 1H NMR of compound 2h (300 MHz, CDCl3) 50 13C{1H} NMR of compound 2h (75 MHz, CDCl3) 51 1H NMR of compound 2h’ (300 MHz, CDCl3) 52 13C{1H} NMR of compound 2h’ (75 MHz, CDCl3) 53 13C{1H} NMR of compound 2i (75 MHz, CDCl3) 55 1H NMR of compound 2j (300 MHz, CDCl3) 56 13C{1H} NMR of compound 2j (75 MHz, CDCl3) 57 1H NMR of compound 2k (300 MHz, CDCl3) 58 13C{1H} NMR of compound 2k (75 MHz, CDCl3) 59 1H NMR of compound 2l (300 MHz, CDCl3) 60 13C{1H} NMR of compound 2l (75 MHz, CDCl3) 61 1H NMR of compound 2m (300 MHz, CDCl3) 62 13C{1H} NMR of compound 2m (75 MHz, CDCl3) 63 1H NMR of compound 2n (300 MHz, CDCl3) 64 13C{1H} NMR of compound 2n (75 MHz, CDCl3) 65 1H NMR of compound 2o (300 MHz, CDCl3) 66 13C{1H} NMR of compound 2o (75 MHz, CDCl3) 67 1H NMR of compound 2p (300 MHz, CDCl3) 68 13C{1H} NMR of compound 2p (75 MHz, CDCl3) 69 1H NMR of compound 2q (300 MHz, CDCl3) 70 13C{1H} NMR of compound 2q (75 MHz, CDCl3) 71 1H NMR of compound 2r (300 MHz, CDCl3) 72 13C{1H} NMR of compound 2r (75 MHz, CDCl3) 73 1H NMR of compound 2s (300 MHz, CDCl3) 74 13C{1H} NMR of compound 2s (75 MHz, CDCl3) 75 1H NMR of 2-Chloro-4-methoxyphenol (300 MHz, CDCl3) 76 13C{1H} NMR of 2-Chloro-4-methoxyphenol (75 MHz, CDCl3) 77 1H NMR of compound 2t (300 MHz, CDCl3) 78 13C{1H} NMR of compound 2t (75 MHz, CDCl3) 79 1H NMR of compound 2u (300 MHz, CDCl3) 80 13C{1H} NMR of compound 2u (75 MHz, CDCl3) 81 1H NMR of compound 2v (300 MHz, CDCl3) 82 13C{1H} NMR of compound 2v (75 MHz, CDCl3) 83 1H NMR of compound 2w (300 MHz, CDCl3) 84 13C{1H} NMR of compound 2w (75 MHz, CDCl3) 85 1H NMR of compound 2x (300 MHz, CDCl3) 86 13C{1H} NMR of compound 2x (75 MHz, CDCl3) 87 1H NMR of compound 2y (300 MHz, CDCl3) 88 13C{1H} NMR of compound 2y (75 MHz, CDCl3) 89 1H NMR of compound 2z (300 MHz, CDCl3) 90 13C{1H} NMR of compound 2z (75 MHz, CDCl3) 91 1H NMR of compound 2aa (300 MHz, CDCl3) 92 13C{1H} NMR of compound 2aa (75 MHz, CDCl3) 93 1H NMR of compound 2bb (300 MHz, CDCl3) 94 13C{1H} NMR of compound 2bb (75 MHz, CDCl3) 95 1H NMR of compound 2cc (300 MHz, CDCl3) 96 13C{1H} NMR of compound 2cc (75 MHz, CDCl3) 97 1H NMR of compound 2cd (300 MHz, CDCl3) 98 13C{1H} NMR of compound 2cd (75 MHz, CDCl3) 99 1H NMR of compound 3a (300 MHz, CDCl3) 100 13C{1H} NMR of compound 3a (75 MHz, CDCl3) 101 1H NMR of 4a (300 MHz, CDCl3) 102 13C{1H} NMR of compound 4a (75 MHz, CDCl3) 103 1H NMR of quinone (300 MHz, CDCl3) 104 13C{1H} NMR of quinone (75 MHz, CDCl3) 105 1H NMR of compound 6 (300 MHz, CDCl3) 106 13C{1H} NMR of compound 6 (75 MHz, CDCl3) 107 Chapter II. Total synthesis of 17−Hydroxymandarone B from (+)−Dehydroabietylamine 108 II-1. Introduction 108 II-2. Result And Discussion 109 II-3. Conclusion 115 II-4. Experimental 116 II.4.1. General information 116 II.4.2. Experimental procedures and data 116 References 130 Appendices 132 1H NMR of compound 8 (300 MHz, CDCl3) 133 13C{1H} NMR of compound 8 (75 MHz, CDCl3) 134 1H NMR of compound 9 (300 MHz, CDCl3) 135 13C{1H} NMR of compound 9 (75 MHz, CDCl3) 136 1H NMR of compound 10 (500 MHz, CDCl3) 137 13C{1H} NMR of compound 10 (125 MHz, CDCl3) 138 1H NMR of compound 7 (300 MHz, CDCl3) 139 13C{1H} NMR of compound 7 (75 MHz, CDCl3) 140 1H NMR of compound 11 (300 MHz, CDCl3) 141 13C{1H} NMR of compound 11 (75 MHz, CDCl3) 142 1H NMR of compound 14 (300 MHz, CDCl3) 143 13C{1H} NMR of compound 14 (75 MHz, CDCl3) 144 1H NMR of compound 15 (500 MHz, CDCl3) 145 13C{1H} NMR of compound 15 (125 MHz, CDCl3) 146 1H NMR of compound 16 (500 MHz, CDCl3) 147 13C{1H} NMR of compound 16 (125 MHz, CDCl3) 148 1H NMR of compound 13 (500 MHz, CDCl3) 149 13C{1H} NMR of compound 13 (125 MHz, CDCl3) 150 1H NMR of compound 12 (500 MHz, CDCl3) 151 13C{1H} NMR of compound 12 (125 MHz, CDCl3) 152 1H NMR of compound 17 (500 MHz, CDCl3) 153 13C{1H} NMR of compound 17 (125 MHz, CDCl3) 154 1H NMR of compound 18 (500 MHz, CDCl3) 155 13C{1H} NMR of compound 18 (125 MHz, CDCl3) 156 1H NMR of compound 6 (500 MHz, CDCl3) 157 13C{1H} NMR of compound 6 (125 MHz, CDCl3) 158 1H NMR of compound 4 (500 MHz, CDCl3) 159 13C{1H} NMR of compound 4 (125 MHz, CDCl3) 160 1H NMR of compound 19 (500 MHz, CDCl3) 161 13C{1H} NMR of compound 19 (125 MHz, CDCl3) 162 1H NMR of compound 5 (500 MHz, CDCl3) 163 13C{1H} NMR of compound 5 (125 MHz, CDCl3) 164 1H NMR of compound 21 (500 MHz, CDCl3) 165 13C{1H} NMR of compound 21 (125 MHz, CDCl3) 166 1H NMR of compound 3 (500 MHz, CDCl3) 167 13C{1H} NMR of compound 3 (125 MHz, CDCl3) 168
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指導教授	侯敦仁(DUEN-REN HOU)	審核日期	2021-8-27
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