Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of Fluorinated Retinal : A C6-C7 s-trans Fixed Retinal Containing a Trifluoromethyl Group at the Terminal Position of the Conjugated System
Yuji HANZAWAMakoto SUZUKIYoshiro KOBAYASHITakeo TAGUCHI
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1991 Volume 39 Issue 4 Pages 1035-1037

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Abstract

For the study of retinal-binding proteins by using fluorine-modified retinals, the all-trans bicyclic trifluororetinal (1), whose C6-C7 bond is fixed in the s-trans form by an ethano bridge, was synthesized. Introduction of a trifluoromethyl group was carried out in 70% yield by photochemical trifluoromethylation of the dienol ether compound (2) with trifluoromethyl iodide. From a comparison of the absorption maximum of 1 with that of the bicyclic retinal (12), it is clear that the electron-withdrawing trifluoromethyl group induces a notable hypsochromic shift (18 nm) of 1.

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© The Pharmaceutical Society of Japan
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