The 2,4,6-tris(trifluoromethyl)phenyl group: Methyl and vinyl ketones and related chemistry

(E)-4-(2',4',5'-trimethoxyphenyl)but-1,3-diene (4) and (E)-4-(2',4',5'-trimethoxyphenyl)but-1-ene (6), bioactive phenylbutanoids of Zingiber cassumunar, were synthesized exclusively with trans geometry. Treatment of methylmagnesium iodide with (E)-2',4',5'-trimethoxycinnamaldehyde (2), an oxidized product of abundantly available toxic (Z)-phenylpropanoid (1) of Acorus calamus, gave (E)-4-(2',4',5'-trimethoxyphenyl)but-3-en-2-ol (3) which upon dehydration with copper sulphate/silica gel under microwave irradiation for 3 min afforded 4 in 58% yield. Further, catalytic hydrogenation of 4 with 10% Pd/C afforded 4-(2',4',5'-trimethoxyphenyl)butane (5) which upon dehydrogenation with DDQ/SiO2 afforded hypolipidemic 6 in 54% yield.

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The 2,4,6-tris(trifluoromethyl)phenyl group: Methyl and vinyl ketones and related chemistry

Cited by 2 publications

References 10 publications

ChemInform Abstract: The 2,4,6‐Tris(trifluoromethyl)phenyl Group: Methyl and Vinyl Ketones and Related Chemistry.

ChemInform Abstract: The 2,4,6‐Tris(trifluoromethyl)phenyl Group: Methyl and Vinyl Ketones and Related Chemistry.

A mild conversion of phenylpropanoid into rare phenylbutanoids: (E)-4-(2′,4′,5′-trimethoxyphenyl)but-1, 3-diene and (E)-4-(2′,4′,5′-trimethoxyphenyl)but-1-ene occurring inZingiber cassumunar

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