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新型手性伪麻黄碱衍生物的合成
Synthesis of new chiral derivatives of d-pseudoephedrine
【摘要】 首次利用单一构型的伪麻黄碱作为亲核试剂与手性5-(S)-烷氧基-3,4-二卤-2-(5H)-呋喃酮在室温下反应,合成了4种新的单一构型的含手性中心的伪麻黄碱衍生物,产率68%~85%。这是对以往相关研究作了进一步的补充,使得麻黄碱和手性5-(S)-烷氧基-3,4-二卤-2-(5H)-呋喃酮反应体系的工作趋于完善。所有化合物均经IR、1HNMR、13CNMR、HRMS确证,为室温下方便地制备含单一构型的手性伪麻黄碱衍生物提供了一条新途径,也为新型麻黄碱类药物的开发打下基础。
【Abstract】 The single-structure d-pseudoephedrine was for the first time used as a new nucleophile in the Michael addition-elimination reactions with chiral 5-(S)-alkoxy-3,4-dibromo-2-(5H)-furanone,to synthesize four kinds of new chiral derivatives at yields ranging from 68% to 85%.The research work provided a good supplement to the previous work to make the reaction system of chiral 5-(S)-alkoxy-3,4-dibromo-2-(5H)-furanone and d-pseudoephedrine more perfect.All the target compounds were identified by IR,1HNMR,13CNMR,and HRMS.It showed us a new way to synthesize the single-structure chiral d-pseudoephedrine derivatives,and a basis of new medicine development was founded.
【Key words】 d-pseudoephedrine; 5-(S)-alkoxy-3,4-dihalo-2-(5H)-furanones; derivatives; Michael addition-elimination reaction;
- 【文献出处】 化学试剂 ,Chemical Reagents , 编辑部邮箱 ,2007年07期
- 【分类号】TQ464.4
- 【被引频次】4
- 【下载频次】478