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Discovering Green, Aqueous Suzuki Coupling Reactions: Synthesis of Ethyl (4-Phenylphenyl)acetate, a Biaryl with Anti-Arthritic Potential
Journal of Chemical Education ( IF 2.5 ) Pub Date : 2012-05-18 00:00:00 , DOI: 10.1021/ed200212p
Nancy E. Costa 1 , Andrea L. Pelotte 1 , Joseph M. Simard 1 , Christopher A. Syvinski 1 , Amy M. Deveau 1
Affiliation  

Suzuki couplings are powerful chemical reactions commonly employed in academic and industrial research settings to generate functionalized biaryls. We have developed and implemented a discovery-based, microscale experiment for the undergraduate organic chemistry laboratory that explores green Suzuki coupling using water as the primary solvent. This experiment exposes students to the professional responsibilities of a pharmaceutical chemist and promotes a problem-solving approach toward learning green chemistry principles. Specifically, students assume the role of a medicinal chemistry researcher striving to identify the greenest and most cost-effective method out of three proposed synthetic approaches to make ethyl (4-phenylphenyl)acetate. Ethyl (4-phenylphenyl)acetate is a precursor to the drug felbinac and demonstrates promise as a lead compound in the discovery of new nonsteroidal anti-inflammatory drugs for the treatment of arthritis.

中文翻译:

发现绿色的水铃木偶联反应:合成具有抗关节炎潜力的联芳基(4-苯基苯基)乙酸乙酯

铃木偶联剂是在学术和工业研究中通常使用的强大化学反应,可生成官能化的联芳基。我们已经为本科生有机化学实验室开发并实施了基于发现的微型实验,该实验探索了以水为主要溶剂的绿色Suzuki偶联。该实验使学生承担药物化学家的专业职责,并提倡一种解决问题的方法来学习绿色化学原理。具体来说,学生将担任药物化学研究人员的角色,努力从三种建议的合成方法(4-苯基苯基)乙酸乙酯中找出最绿色,最具成本效益的方法。
更新日期:2012-05-18
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