臺灣博碩士論文加值系統

中文摘要
在本研究中， 1-萘醇(1-naphthol) (1)和溴化丙烯(allyl bromide)以無水丙酮當溶媒，在無水K2CO3存在下迴流反應，得到1-丙烯氧萘(1-allyloxynaphthalene)(2)，將化合物(2)在高溫（180。C）進行克萊森轉位（Claisen Rearrengement）後得到產物2-丙烯基-1-萘醇(2-allyl-1-naphthol) (3) ，然後將2-丙烯基-1-萘醇(2-allyl-1-naphthol) (3)和過量的1,2-二氯乙烷（1,2-dichloroethane）反應得到 2-丙烯基-1-（2-氯乙氧基）萘 [2-allyl-1-(2-chloroethoxy)naphthalene] (4)。再將化合物2-丙烯基-1-（2-氯乙氧基）萘[2-allyl-1-(2-chloroethoxy)- naphthalene] (4)和強鹼t-BuOK反應進行丙烯基的異構化，同時脫去HCl得到2-（1-丙烯基）-1-乙烯氧基萘[2-（1-propenyl）-1-vinyloxynaphthalene]（5）。
最後，將2-（1-丙烯基）-1-乙烯氧基萘 [2-（1-propenyl）-1-vinyloxynaphthalene]（5）利用Grubbs催化劑，經過閉環置換反應（RCM）得到預期產物，萘酚呋喃 (naphtho [1,2-b]furan) (6)。

1-Allyloxynaphthalene (2), prepared from 1-naphthol (1) and allyl bromide, was heated at high temperature（180℃）to undergo Claisen rearrengement to furnish 2-allyl-1-naphthol (3). Subsequently this naphthol (3) was reacted with excess 1,2-dichloroethane and aq. NaOH in the presence of tetrabutylammonium bromide as phase transfer catalyst to undergo two phases reaction to give 2-allyl-1-(2-chloroethoxy)- naphthalene] (4). By treating compound (4) with potassium tert-butoxide to undergo isomerization of allyl group, and dehydrochlorination in one pot, gave 2-(1-propeny)-1-vinyl-oxynaphthalene (5) as a precursor for ring-closing metathesis reaction.
Finally, compound (5) was cyclized via ring-closing metathesis by Grubbs catalyst to furnish the desired compound, naphtho[1,2-b]furan(6) in good over-all yield.

目錄
中文摘要…………………………………………………….…………..5
英文摘要………………………………………………………………...6
第一章 前言…………………………………………………………...7
第二章 研究動機…………………………………………………….21
第三章 研究策略與合成設計途徑………………………………….23
第四章 結果與討論……………………………………………….…25
第五章 實驗部份………………………………………..………….. 34
一、 實驗試劑…………………………………………………… 34
二、 溶媒的處理………………………………………………… 35
三、 實驗步驟…………………………………………………… 36
參考文獻……………………………………………………………… 44
附圖目錄………………………………………………………………..47

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