系統識別號 | U0002-0603201214113000 |
---|---|
DOI | 10.6846/TKU.2012.00229 |
論文名稱(中文) | 利用銅催化溴苯乙腈衍生物合成螺-吲哚酮化合物 |
論文名稱(英文) | Cu(I)-Catalyzed synthesis of spiro-oxindoles from 2-bromophenylacetonitrile derivatives |
第三語言論文名稱 | |
校院名稱 | 淡江大學 |
系所名稱(中文) | 化學學系碩士班 |
系所名稱(英文) | Department of Chemistry |
外國學位學校名稱 | |
外國學位學院名稱 | |
外國學位研究所名稱 | |
學年度 | 100 |
學期 | 1 |
出版年 | 101 |
研究生(中文) | 傅軍豪 |
研究生(英文) | Jun-Hao Fu |
學號 | 698160321 |
學位類別 | 碩士 |
語言別 | 繁體中文 |
第二語言別 | |
口試日期 | 2012-01-03 |
論文頁數 | 179頁 |
口試委員 |
指導教授
-
謝仁傑(jchsieh@mail.tku.edu.tw)
委員 - 徐秀福(hhsu@mail.tku.edu.tw) 委員 - 陳榮傑(rjchein@chem.sinica.edu.tw) |
關鍵字(中) |
烏爾曼反應 串聯反應 螺-吲哚酮 |
關鍵字(英) |
Ullmann Reaction Domino Reaction spiro-oxindoles |
第三語言關鍵字 | |
學科別分類 | |
中文摘要 |
使用銅催化不同取代基的鄰溴苯基乙腈合成多種螺-吲哚酮衍伸物的方法被開發出來,此方法是有效率的,且起始物為便宜以及方便被利用的符合經濟效益。此方經由Domino-Ullmann-type交互耦合反應法可以容易的建構螺-吲哚酮結構,且反應條件溫和。最後我們使用此方法合成天然物生物鹼(±)-coerulescine和(±)-horsfiline並且有好的總產率。 |
英文摘要 |
An efficient copper-catalyzed approach to spiro-oxindoles derivatives has been developed, and the protocol uses cheap and readily available substituted 2-bromophenylacetonitrile as the starting materials as well as economical. This method can be easy for constructing spiro-oxindoles via Domino-Ullmann-type coupling under mild conditions. Finally, we synthesized natural products of the oxindole alkaloids (±)-coerulescine and (±)-horsfiline by this method in excellent overall yields. |
第三語言摘要 | |
論文目次 |
目錄 第壹章 前言...............................................1 1.1 Ullmann Reaction.......................................1 1.2 Ullmann Reaction with Annulation.......................3 1.3 Ullmann Reaction with Domino Reaction..................6 1.4 研究動機..............................................11 1.5 Oxindole..............................................13 第貳章 結果與討論.........................................14 2.1最佳化反應條件.........................................14 2.2不同官能基取代的影響...................................18 2.3 結論..................................................23 第參章 起始物置備-實驗步驟................................24 3.1起始物合成-scheme .....................................24 3.2起始物合成-實驗步驟....................................28 第肆章 產物置備...........................................50 第伍張 參考資料...........................................59 Scheme: Scheme 1 銅催化鄰鹵素苯乙腈合成吲哚銅反應機構.............12 Scheme 2 有螺─吲哚酮結構的天然物與藥物...................13 Table : Table 1. 最佳化條件以碘苯基乙腈合成吲哚酮.................14 Table 2. 不同配位對碘苯基乙腈合成吲哚酮的影響.............16 Table 3. 最佳化條件以溴苯基乙腈合成吲哚酮.................17 Table 4. 不同官能基取代的溴苯基乙腈合成吲哚酮結構.........20 NMR 光譜 H1 NMR 分子a2.............................................62 C13 NMR 分子a2............................................63 H1 NMR 分子a3.............................................64 C13 NMR 分子a3............................................65 H1 NMR 分子a4.............................................66 C13 NMR 分子a4............................................67 H1 NMR 分子a5.............................................68 C13 NMR 分子a5............................................69 H1 NMR 分子a6.............................................70 C13 NMR 分子a6............................................71 H1 NMR 分子a7.............................................72 C13 NMR 分子a7............................................73 H1 NMR 分子a8.............................................74 C13 NMR 分子a8............................................75 H1 NMR 分子a9.............................................76 C13 NMR 分子a9............................................77 H1 NMR 分子a10............................................78 C13 NMR 分子a10...........................................79 H1 NMR 分子a11............................................80 C13 NMR 分子a11...........................................81 H1 NMR 分子a12............................................82 C13 NMR 分子a12...........................................83 H1 NMR 分子a13............................................84 C13 NMR 分子a13...........................................85 H1 NMR 分子a14............................................86 C13 NMR 分子a14...........................................87 H1 NMR 分子a15............................................88 C13 NMR 分子a15...........................................89 H1 NMR 分子a16............................................90 C13 NMR 分子a16...........................................91 H1 NMR 分子a17............................................92 C13 NMR 分子a17...........................................93 H1 NMR 分子a18............................................94 C13 NMR 分子a18...........................................95 H1 NMR 分子a19............................................96 C13 NMR 分子a19...........................................97 H1 NMR 分子a20............................................98 C13 NMR 分子a20...........................................99 H1 NMR 分子a21...........................................100 C13 NMR 分子a21..........................................101 H1 NMR 分子a22...........................................102 C13 NMR 分子a22..........................................103 H1 NMR 分子b1............................................104 C13 NMR 分子b1...........................................105 H1 NMR 分子b2............................................106 C13 NMR 分子b2...........................................107 H1 NMR 分子b3............................................108 C13 NMR 分子b3...........................................109 H1 NMR 分子b4............................................110 C13 NMR 分子b4...........................................111 H1 NMR 分子b5............................................112 C13 NMR 分子b5...........................................113 H1 NMR 分子b6............................................114 C13 NMR 分子b6...........................................115 H1 NMR 分子b7............................................116 C13 NMR 分子b7...........................................117 H1 NMR 分子b8............................................118 C13 NMR 分子b8...........................................119 H1 NMR 分子b9............................................120 C13 NMR 分子b9...........................................121 H1 NMR 分子b10...........................................122 C13 NMR 分子b10..........................................123 H1 NMR 分子b11...........................................124 C13 NMR 分子b11..........................................125 H1 NMR 分子b12...........................................126 C13 NMR 分子b12..........................................127 H1 NMR 分子b13...........................................128 C13 NMR 分子b13..........................................129 H1 NMR 分子b14...........................................130 C13 NMR 分子b14..........................................131 H1 NMR 分子b15...........................................132 C13 NMR 分子b15..........................................133 H1 NMR 分子b16...........................................134 C13 NMR 分子b16..........................................135 H1 NMR 分子b17...........................................136 C13 NMR 分子b17..........................................137 H1 NMR 分子b18...........................................138 C13 NMR 分子b18..........................................139 H1 NMR 分子b19...........................................140 C13 NMR 分子b19..........................................141 H1 NMR 分子b20...........................................142 C13 NMR 分子b20..........................................143 H1 NMR 分子b21...........................................144 C13 NMR 分子b21..........................................145 H1 NMR 分子b22...........................................146 C13 NMR 分子b22..........................................147 H1 NMR 分子c.............................................148 C13 NMR 分子c............................................149 H1 NMR 分子d.............................................150 C13 NMR 分子d............................................151 H1 NMR 分子e1............................................152 C13 NMR 分子e1...........................................153 H1 NMR 分子e2............................................154 C13 NMR 分子e2...........................................155 H1 NMR 分子f1............................................156 C13 NMR 分子f1...........................................157 H1 NMR 分子f2............................................158 C13 NMR 分子f2...........................................159 H1 NMR 分子f3............................................160 C13 NMR 分子f3...........................................161 H1 NMR 分子g.............................................162 C13 NMR 分子g............................................163 H1 NMR 分子h1............................................164 C13 NMR 分子h1...........................................165 H1 NMR 分子h2............................................166 C13 NMR 分子h2...........................................167 H1 NMR 分子h3............................................168 C13 NMR 分子h3...........................................169 H1 NMR 分子h4............................................170 C13 NMR 分子h4...........................................171 H1 NMR 分子h5............................................172 C13 NMR 分子h5...........................................173 H1 NMR 分子j2............................................174 C13 NMR 分子j2...........................................175 H1 NMR 分子j3............................................176 H1 NMR 分子j4............................................178 C13 NMR 分子j4...........................................179 |
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