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研究生：	姜廷達 Chiang, Ting-Ta
論文名稱：	應用麥可加成反應來合成4, 6-二苯-1氫-萉-1-酮和4, 6-二苯-2氫-吡喃羧酸酯 Michael addition to synthesize 4, 6-diphenyl-1H-phenalen-1-one and ethyl 2-oxo-4, 6-diphenyl-2H-pyran-3-carboxylate
指導教授：	姚清發 Yao, Ching-Fa
學位類別：	碩士 Master
系所名稱：	化學系 Department of Chemistry
論文出版年：	2017
畢業學年度：	105
語文別：	中文
論文頁數：	259
中文關鍵詞：	麥可加成、二苯丙炔酮、1-萘酚、三氟化硼、萉酮、丙二酸酯、吡喃酮
英文關鍵詞：	Michael addition, 1-naphthol, trifloroborane, malonate, pyrone
DOI URL：	https://doi.org/10.6345/NTNU202202528
論文種類：	學術論文
相關次數：	點閱：471 下載：2
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查詢本校圖書館目錄查詢臺灣博碩士論文知識加值系統勘誤回報

科學家們從許多不同的生物體中分離出許多具有生物活性的天然物，而其中有些分子具有萉酮及吡喃等特定結構。
本論文分為兩個部分，皆是透過二苯丙炔酮作為起始骨架，進行特定結構分子的合成，第一部分，先回顧這幾年來此一分子的性質及功用，研究及合成，是探討藉由1-萘酚與二苯丙炔酮進行一連串的合成過程以合成萉酮這一類的植物抗菌素，反應過程中透過三氟化硼(Boron trifluoride diethyl etherate，簡稱BF3)進行酸催化進行麥可加成反應，以合成萉酮化合物。
第二部分是探討藉由丙二酸酯與二苯丙炔酮進行一連串的合成過程，反應過程藉由路易斯鹼氫氧化鈉催化二乙基丙二酸酯先形成烯醇，再藉由麥可加成反應對三鍵炔類進行加成，先形成丙二烯(allene)，最終得到一高產率的吡喃酮化合物。

Scientists have isolated many occurring natural substances from many different organisms, and some of them have specific structure such as pyrone and phenalene.

This thesis covers the combination of two separate works. The two parts both synthesized by the diphenylpropynone as the original skeleton. Among them, the first work refers to some references about the natures, functions of this molecule, and some researches and synthesis over the past few years. To explore how to synthesize this kind of molecule by series of processes, we were carried out with 1-naphthol and diphenylpropynone which is a kind of novel phytoalexins. The Lewis acid (boron trifluoride diethyl etherate (BF3)) catalyzed Michael addition reaction to synthesize phenalenone compounds during this reaction.

The second part is to explore series of synthetic processes by the combination of diethylmalonate and diphenylpropynone. Sodium hydroxide as a Lewis base catalyzed malonate to form enolate, involving the addition of alkyne to produce allene. At last, we got the pyrone compounds in a high yield.

目錄
中文摘要………………………………………………………………………………………………I
英文摘要………………………………………………………………………………………………II
第壹章、    前言
1. 親核性加成……………………………………………………………………………P. 03
1-1. 1, 2-加成…………………………………………………………………………P. 03
1-2. 1, 4-加成(C-C)……………………………………………………………P. 05
1-3. 1, 4-加成(C-O)……………………………………………………………P. 08
1-4. 1, 4-加成(C-S) …………………………………………………………P. 09
1-5. 1, 4-加成(C-N) …………………………………………………………P. 10
1-6. 1, 6-加成…………………………………………………………………………P. 11
1-7. 1, 8-加成…………………………………………………………………………P. 12

2. 二苯丙炔酮的應用………………………………………………………………P. 13

3. 萘酚的簡介……………………………………………………………………………P. 17
3-1. 親電性取代反應……………………………………………………………P. 18
3-2. 1, 2-加成反應………………………………………………………………P. 20
3-3. 1, 4-加成反應 ……………………………………………………………p. 20
3-4. 還原反應 …………………………………………………………………………P. 21
3-5. 金屬偶聯反應 ………………………………………………………………P. 21
3-6. 其他………………………………………………………………………………………P. 22

4. 參考文獻………………………………………………………………………………P. 23

第貳章、    麥可加成合成4, 6-二苯-1氫-萉-1-酮

1.  phenalenone的介紹…………………………………………………P. 29

2. 文獻回顧………………………………………………………………………………P. 33
2-1. The reaction of the PN…………………………………P. 33
2-2. PN synthesis……………………………………………………………P. 38
a. One component synthesis 1H PN……………………P. 38
b. Two component synthesis 1H PN……………………P. 40
c. Synthesis 2-Ph PN……………………………………………………P. 41
d. Synthesis 3-Ph PN……………………………………………………P. 41
e. Synthesis 4-OMe PN…………………………………………………P. 42
f. Synthesis 4-Ph PN……………………………………………………P. 42
g. Synthesis 5-Ph PN……………………………………………………P. 45
h. Synthesis 6-Ph PN……………………………………………………P. 46
i. Synthesis 6-OH PN……………………………………………………P. 46
j. Synthesis 7-Ph PN……………………………………………………P. 47
k. Synthesis 8-Ph PN……………………………………………………P. 48
l. Synthesis 9-Ph PN……………………………………………………P. 49

3. 研究目標………………………………………………………………………………P. 50
 
4. 結果與討論…………………………………………………………………………P. 52
4-1. 最佳化條件探討…………………………………………………………P. 52
4-2. 化合物3取代基效應的探討……………………………………P. 61
4-3. 以聚焦式微波加熱法改良傳統加熱法之探討P. 64
4-4. 反應機構的探討…………………………………………………………P. 67

5. 結論………………………………………………………………………………………P. 68

6. 參考文獻……………………………………………………………………………P. 69

第叁章、合成4, 6-二苯-2氫-吡喃羧酸酯
1. 吡喃化合物的簡介…………………………………………………………P. 74
2. 文獻回顧……………………………………………………………………………P. 77
2-1. 吡喃衍生物之合成……………………………………………………P. 77
2-2. 吡喃衍生物之反應……………………………………………………P. 81

3. 研究目標……………………………………………………………………………P. 85
4. 結果與討論………………………………………………………………………P. 87
4-1. 化合物8最佳化條件探討………………………………………P. 87
4-2. 取代基效應…………………………………………………………………P. 91
4-3. 反應機構的探討…………………………………………………………P. 95

5. 結論……………………………………………………………………………………P. 96
6. 參考文獻…………………………………………………………………………P. 97
第肆章、實驗部份
1.    分析儀器及基本實驗操作………………………………P. 101
1-1.    一般實驗方法……………..…………………………….P. 101

2. 第貳章實驗步驟…………………………………………………………P. 103
2-1.    合成二苯丙炔酮3的步驟：(3a- 3q )P. 103
2-2.    合成苯丙炔酮3的步驟：(3r- 3s)……P. 104
2-3.    合成2-溴1-萘酚4b的步驟：……………….P. 105
2-4.    合成2-氯1-萘酚4c的步驟：…………………P. 106
2-5.    合成中間物 5步驟：……………………………….P. 108
2-6.    合成phenalenone 6步驟：(6a-6t) P. 108

3. 第貳章光譜資料………………………………………………………P. 110

4. 第叁章實驗步驟……………………………………………………P. 120
4-1.    合成diallyl malonate的步驟：(7d)P. 120
4-2.    合成diphenyl malonate的步驟：(7e)p. 121
4-3.    合成dibenzyl malonate的步驟：(7f)P. 121
4-4.    合成4, 6-diphenyl pyran-3-carboxylate(8a-8u)P. 122

5. 第叁章光譜資料……………………………………………………………P. 123

 

6. 單晶繞射X-Ray分析結構圖……………………………...….…P. 135
6-1.    Single-Crystal X-ray Diffraction of 5i…P. 135
6-2.    Single-Crystal X-ray Diffraction of 6s…P. 146
6-3.    Single-Crystal X-ray Diffraction of 8b…P. 158
6-4.    Single-Crystal X-ray Diffraction of 9 …P. 167

7. 1H-NMR及13C-NMR 光譜附圖………………………P. 179
                                

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