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Novel lipidic enaminones from a C 18 keto‐allenic ester
Author(s) -
Lie Ken Jie Marcel S. F.,
Lau Maureen M. L.
Publication year - 2000
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-000-0629-4
Subject(s) - chemistry , yield (engineering) , primary (astronomy) , glycine , valine , leucine , allene , organic chemistry , alanine , medicinal chemistry , amino acid , catalysis , biochemistry , physics , materials science , astronomy , metallurgy
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.