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Novel lipidic enaminones from a C18 keto-allenic ester

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Lipids

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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Abbreviations

HRMS:

high-resolution mass spectral analysis

IR:

infrared

NMR:

nuclear magnetic resonance

2D-NOESY:

two-dimensional nuclear Overhauser enhancement spectroscopy

TLC:

thin-layer chromatography

TMS:

tetramethylsilane

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Authors and Affiliations

  1. Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong

    Marcel S. F. Lie Ken Jie & Maureen M. L. Lau

Authors
  1. Marcel S. F. Lie Ken Jie
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  2. Maureen M. L. Lau
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Correspondence to Marcel S. F. Lie Ken Jie.

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Lie Ken Jie, M.S.F., Lau, M.M.L. Novel lipidic enaminones from a C18 keto-allenic ester. Lipids 35, 1135–1145 (2000). https://doi.org/10.1007/s11745-000-0629-4

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  • DOI: https://doi.org/10.1007/s11745-000-0629-4

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