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研究生：	楊惠婷 Yang, Huei-Ting
論文名稱：	苯並呋喃及異吲哚啉酮並異喹啉衍生物之合成 Synthesis of Benzofuran, Fused Isoindolinone and Isoquinoline Derivatives
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：	2016
畢業學年度：	104
語文別：	中文
論文頁數：	260
中文關鍵詞：	苯並呋喃、異吲哚啉酮並異喹啉、一鍋化、銅催化、鈀催化
英文關鍵詞：	Benzofuran, one-pot synthesis, Copper-catalyzed, Palladium-catalyzed
DOI URL：	https://doi.org/10.6345/NTNU202204798
論文種類：	學術論文
相關次數：	點閱：121 下載：2
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本論文分為兩部分，第一部分主要探討硝基化合物的化學，主題為萘並呋喃
衍生物的合成，利用簡單的一鍋化方式在鹼性條件下進行反應，首先β-硝基烯衍生物及2-萘酚於室溫下先進行1,4-麥可加成後再進行分子內合環反應，於溫和的條件下得到產率相當不錯的多種萘並呋喃衍生物。

第二部分主要探討以2-碘苯甲醯胺衍生物與末端炔為起始物經由兩步驟合
成異吲哚啉酮稠合異喹啉的衍生物，第一步利用銅試劑催化進行薗頭耦合反應及分子內合環得到多種異吲哚啉酮衍生物且有相當不錯的產率，第二部則是利用醋酸鈀催化分子內赫克反應合成出異吲哚啉酮稠合異喹啉的衍生物，兩步均利用低催化劑量的催化劑及溫合的條件即可得乾淨且產率不錯的產物。

The content of the thesis is divided into two parts. The first part focuses on the chemistry of the nitro alkenes and its application in the synthesis of naphthofuran derivatives. The methodology is based on one-pot base mediated tandem reaction of β-nitrostyrene derivatives and 2-naphthol, 1,4-Michael addition and intramolecular cyclization. A wide variety of naphthofuran derivatives were synthesized in relatively good yields under mild condition.

The second part describes about the synthesis of fused isoindolinone and isoquinoline derivatives in two step processes starting from 2-iodobenzamide derivatives and terminal alkynes. In the first step, copper(II) catalyst was used for the Sonogashira coupling and intramolecular cyclization in the reaction of 2-iodobenzamide derivatives and terminal alkynes to obtain isoindolinone derivatives in good excellent yields. The second step is an intramolecular Heck reaction which was catalyzed by palladium diacetate. In both steps the catalyst loading was low and the desired products were obtained in moderate yields. The conditions used here are mild and reactions are clean in most the cases.

目錄
中文摘要........................................................................................................................ I
英文摘要.......................................................................................................................  II
壹、苯並呋喃衍生物的合成
1-1、前言  ......................................................................................................................  1
1-1-1、呋喃衍生物的介紹  ...................................................................................  1
1-1-2、苯並呋喃衍生物的介紹  ...........................................................................  2
1-1-3、苯並呋喃衍生物的合成  ...........................................................................  3
1-1-4、萘並呋喃衍生物的合成  ...........................................................................  5
1-1-5、鮑德溫規則(Baldwin’s rule)  .....................................................................  9
1-1-6、腦文格縮合反應(Knoevenagel Condensation)  ......................................  10
1-2、研究目標  ............................................................................................................  12
1-3、實驗結果與討論  ................................................................................................  13
1-3-1、硝基烷(Nitroalkane)的合成  ...................................................................  13
1-3-2、硝基烯(Nitroalkene)的合成  ...................................................................  14
1-3-3、萘並呋喃衍生物的合成  .........................................................................  17
1-4、結論  ....................................................................................................................  29
1-5、實驗部分  ............................................................................................................  29
1-5-1、一般實驗方法  .........................................................................................  29
1-5-2、實驗步驟  .................................................................................................  31
1-6、參考文獻  ............................................................................................................  32
1-7、光譜資料  ............................................................................................................  35
1-8、X-ray 資料  ..........................................................................................................  52
1-9、光譜附圖  ............................................................................................................  76

貳、異吲哚啉酮稠合異喹啉衍生物的合成
2-1、前言  ..................................................................................................................  153
2-1-1、異吲哚啉酮(isoindolinone)衍生物的介紹 ..........................................  153
2-1-2、異喹啉(isoquinoline)衍生物的介紹  ....................................................  154
2-1-3、異吲哚啉酮(isoindolinone)衍生物的合成 ..........................................  155
2-1-4、異喹啉(isoquinoline)衍生物的合成  ....................................................  156
2-1-5、鈀金屬催化的人名反應  .......................................................................  157
2-1-6、薗頭耦合反應(Sonogashira coupling)  .................................................  158
2-1-7、赫克反應(Heck reaction)  ......................................................................  160
2-2、研究目標  ..........................................................................................................  164
2-3、實驗結果與討論  ..............................................................................................  165
2-3-1、2-碘苯甲醯胺(2-iodobenzamide)衍生物的合成  .................................  165
2-3-2、異吲哚啉酮稠合二氫異喹啉的衍生物的合成  ...................................  166
2-3-3、最佳化條件篩選  ...................................................................................  167
2-3-4、不同取代基效應之測試  .......................................................................  173
2-3-5、反應機構探討  .......................................................................................  183
2-4、結論  ..................................................................................................................  185
2-5、實驗部分  ..........................................................................................................  185
2-5-1、一般實驗方法  .......................................................................................  185
2-5-2、實驗步驟  ...............................................................................................  187
2-6、參考文獻  ..........................................................................................................  189
2-7、光譜資料  ..........................................................................................................  192
2-8、X-ray 資料  ........................................................................................................  205
2-9、光譜附圖  ..........................................................................................................  223
                                

壹、萘並呋喃衍生物的合成
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貳、異吲哚啉酮稠合異喹啉衍生物的合成
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