Novel lipidic enaminones from a C18 keto-allenic ester |
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Authors: | Marcel S F Lie Ken Jie Maureen M L Lau |
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Affiliation: | (1) Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong |
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Abstract: | Primary amines (ammonia, methyl, propyl, octyl, octadecyl, phenyl, benzyl, phenethyl) including methyl esters of amino acids
(glycine, dl-alanine, l-valine, l-leucine, L-tyrosine, and l-methionine), and secondary amines (dimethyl, diethyl, dipropyl, diisopropyl, dioctyl, and diphenyl) attack regiospecifically
the central carbon atom of the allene system of methyl 12-keto-9,10-octadecadienoate (1) to give the corresponding lipidic enaminone derivatives (2–21) with an average yield of 77%. The E- and Z-configuration of the enaminone system of these novel lipid derivatives was confirmed
by infrared and nuclear magnetic resonance spectroscopic techniques. Primary amines furnished Z-enaminones, while secondary
amines gave E-enaminones. |
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