Novel lipidic enaminones from a C18 keto-allenic ester.
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.
Jie
M S
MS
Department of Chemistry, The University of Hong Kong, China. hrsclkj@hkucc.hku.hk
Lau
M M
MM
D001671:Biochemistry / Q000379:methods; D002244:Carbon / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D007259:Infrared Rays; D008055:Lipids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D013053:Spectrophotometry
D004952:Esters; D008055:Lipids; D002244:Carbon