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  • 學位論文

碘化鉀和水溶劑在酸性條件下進行碘環化之研究

Iodocyclization with potassium iodide and aqueous solvent under acidic conditions

指導教授 : 莊敬

摘要


藉由鹵素的親電加成反應產生烯烴類產物,是非常有效率且發展超過百年的反應方法,C=C鍵的鹵化反應更廣泛地應用在有機合成當中。藉由碘環化作用(iodocyclization reaction)以2-烯丙基苯酚類作為骨架之化合物並與C=C活化氧和碘並形成二氫苯並呋喃(dihydrobenzofuran)類的化合物,本篇除了以2-烯丙基苯酚類作為骨架接上不同官能基之化合物進行碘環化反應之外,也嘗試以4-戊烯酸做為骨架的化合物在水與乙晴作為溶劑並在酸性的條件之下及以光作為反應催化劑的有氧合成進行碘環化反應。本篇研究目標為探討比較不同的反應條件下並提升催化效率。

並列摘要


The electrophilic addition reaction of halogens to generate olefinic products is an efficient and well-established method in organic synthesis, with applications spanning over a century. The halogenation of C=C bonds is widely utilized in organic synthesis. In this study, we explore the iodocyclization reaction using 2-allylphenol derivatives as the framework compounds, wherein they react with activated oxygen and iodine to form dihydrobenzofuran compounds. Apart from utilizing 2-allylphenol derivatives with various functional groups for iodocyclization, we also attempt iodocyclization reactions using 4-pentenoic acid derivatives as the framework compounds. These reactions are carried out in water and ethyl acetate as solvents, under acidic conditions, and using light as the catalytic agent for aerobic synthesis. The objective of this study is to compare different reaction conditions and enhance catalytic efficiency.

並列關鍵字

Iodocyclization 2-allyl phenol Visible light

參考文獻


(1) Kristianslund, R.; Tungen, J. E.; Hansen, T. V. Catalytic enantioselective iodolactonization reactions. Organic & Biomolecular Chemistry 2019, 17 (12), 3079-3092, 10.1039/C8OB03160F. DOI: 10.1039/C8OB03160F.
(2) TL, L.; DA, W.; VF, R.; SW, Z. Foye’s Principles of Medicinal Chemistry, 7th ed. Lippincott Williams & Wilkins:Philadelphia 2012.
(3) Bokoskie, T.; Cunningham, C.; Kornman, C.; Kesharwani, T.; Pattabiraman, M. Iodocyclization in Aqueous Media and Supramolecular Reaction Control Using Water-Soluble Hosts. ACS Omega 2019, 4 (18), 17830-17836. DOI: 10.1021/acsomega.9b02466.
(4) Jiang, X.; Liu, W.; Zhang, W.; Jiang, F.; Gao, Z.; Zhuang, H.; Fu, L. Synthesis and antimicrobial evaluation of new benzofuran derivatives. Eur J Med Chem 2011, 46 (8), 3526-3530. DOI: 10.1016/j.ejmech.2011.04.053 From NLM.
(5) Xu, Z.; Zhao, S.; Lv, Z.; Feng, L.; Wang, Y.; Zhang, F.; Bai, L.; Deng, J. Benzofuran derivatives and their anti-tubercular, anti-bacterial activities. European Journal of Medicinal Chemistry 2019, 162, 266-276. DOI: https://doi.org/10.1016/j.ejmech.2018.11.025.

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