研究生: |
古貫君 Ku, Kuan-Chun |
---|---|
論文名稱: |
利用有機膦試劑誘導α,β-不飽合羰基衍生物進行β位醯化反應 Direct β-acylation of α,β-unsaturated Carbonyl Derivatives with Acyl chloride by Organophosphane |
指導教授: |
林文偉
Lin, Wen-Wei |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2018 |
畢業學年度: | 106 |
語文別: | 中文 |
論文頁數: | 50 |
中文關鍵詞: | β位醯化反應 |
英文關鍵詞: | β-acylation |
DOI URL: | http://doi.org/10.6345/THE.NTNU.DC.013.2018.B05 |
論文種類: | 學術論文 |
相關次數: | 點閱:105 下載:3 |
分享至: |
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 |
此論文利用本實驗室開發出來的合成方法β位醯化反應(β-acylation),對兩種天然物肉桂酸(Cinnamic acid)、查耳酮(Chalcone)衍生物進行官能化,希望可以藉由改變起始物的結構,找出β位醯化反應發生的原理和限制。
第一部分:
查耳酮為一具有α,β-不飽和羰基化合物,其自然界相關衍生物常可於柑橘類的果皮中發現,目前也廣泛用在多種食品添加劑和藥物化學中,我們利用查耳酮衍生物當作起始物並利用有機膦試劑進行β位醯化反應,希望能夠了解β位醯化反應的限制和成因。
第二部分:
肉桂酸為具有α,β-不飽和羰基化合物,常見於植物中,目前肉桂衍生物也被廣泛使用於化學工業和藥物化學中,我們起初想要在其β位進行醯化反應,卻得一呋喃酮衍生物,而其中有兩種推測的反應機構,都會經過β位醯化反應產物,引起我們的好奇。
Part I:
We have developed direct β-acylation of α,β-unsaturated 1,3-diketones derivative by organophosphane under mild conditions. The single isomeric product could be afforded. Remarkably, selective formation of β-acylation products or furans could be controlled under the designed reaction condition.
Part II:
We have developed a organophosphane-mediated reaction for the synthesis of furanones from cinnamic acid derivatives in moderate to good yields under mild conditions. We wish to study this chemistry further, explore the reaction mechanism, and develop a standard protocol for the synthesis of a variety of α,β-unsaturated lactones.
1.Mahapatra, D.K.; Bharti, S.K. .; Asati, V. Current Topics in Medicinal Chemistry. 2017, 17, 146-36ba.
2.Budavari, S.; O'Neil, M.; Smith, Ann; Heckelman, P.; Obenchain, J. The Merck Index : An Encyclopedia of Drugs, Chemicals and Biologicals, 12rd ed.; CRC Press: Auburn, WA, U.S.A., 1996.
3. Garbe, D. (2000). Cinnamic Acid. Ullmann’s Encyclopedia of Industrial Chemistry
4.Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A.Wilkinson. Blackwell Scientific Publications, Oxford (1997).
5."The Nobel Prize in Physiology or Medicine 1953". Nobelprize.org. Nobel Media AB 2014. Web. 25 May 2018
6.(a)Ruzi, R. ; Zhang, M.; Ablajan, K.; Zhu, C. J. Org. Chem. 2017, 82 , 12834–12839.(b)Vekariya, R. H.; Aube, J. Org. Lett. 2016, 18, 3534-3538.
(c)Benischke, A. D.; Leroux, M.; Knoll, I.; Knochel, P. Org. Lett. 2016, 18, 3626−3629.(d)Adib, M.; Pashazadeh, R.; Rajai-Daryasarei, S.; Kabiri, R.; Jahani, M. RSC Adv. 2016, 6, 110656– 110660.(e)McAteer, D. C.; Javed, E.; Huo, L.; Huo, S. Org. Lett. 2017, 19, 1606.(f)Dreis, A. M.; Douglas, C. J. J. Am. Chem. Soc. 2009, 131, 37cl− 37cm.
7.Lee, P.-Y.; Liang, P.; Yu, W.-Y. Org. Lett. 2017, 19 , 2082–2085.
8.(a)Chenguang Zheng.; Xiang Liu.; Cheng Ma. J. Org. Chem. 2017, 82, 6940-6945.(b)Rahul B.; Sonawane.; Nishant K. Rasal.; Sangeeta V. Jagtap. Org. Lett. 2017 19, 2078-2081.
9.Yi Dua, Yunyun Liu.* Jie-Ping Wan.*J. Org. Chem. 2018, 83 ,337cc–337ch.
10.Yasunori Toda.; Tomoyuki Sakamoto.; Yutaka Komiyama.; Ayaka Kikuchi.; Hiroyuki Suga. ACS Catalysis. 2017, 7, 6150-6154.
11.Vilas B. Gade.; Anuj K. Rathi.; Sujit B. Bhalekar.; Jiri Tucek.; Ondrej Tomanec.; Rajender S. Varma.; Radek Zboril.; Sharad N. Shelke.; Manoj B. Gawande.
ACS Sustainable Chemistry & Engineering. 2017, 5, 336cn-3320.
12. Paul, S.; Gupta, M. Synth. Commun. 2005, 35, 213-222.