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THE PAPILIONACEOUS ALKALOIDS: XV. THE STRUCTURE AND THE PARTIAL SYNTHESIS OF RHOMBIFOLINE

 

作者: William F. Cockburn,   Léo Marion,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1952)
卷期: Volume 30, issue 2  

页码: 92-101

 

ISSN:0008-4042

 

年代: 1952

 

DOI:10.1139/v52-014

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

Rhombifoline is isomeric with thermopsine and anagyrine, and, like both these alkaloids, contains an α-pyridone ring. It can be dealkylated to cytisine, and, on catalytic hydrogenation, yields octahydrodesoxyrhombifoline, which is identical with hexahydrodesoxy-N-(n-butyl)-cytisine, the hydrogenation product of N-(n-butyl)-cytisine. The results of the hydrogenation thus indicate that the molecule of rhombifoline contains a third double bond, which is shown by its infrared spectrum to be located at a terminal methylene group. Rhombifoline is therefore N-(but-3-enyl)-cytisine, a conclusion which was confirmed by the partial synthesis of the alkaloid from cytisine.

 

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