103499-92-9Relevant articles and documents
Synthesis of three retinal models, including the 10-s-cis-locked retinal, all-E-12,19-methanoretinal
Groesbeek, M.,Steen, R. van der,Vliet, J. C. van,Vertegaal, L. B. J.,Lugtenburg, J.
, p. 427 - 436 (2007/10/02)
All-E-12,19-methanoretinal (1) is distinguished by the presence of the locked 10-s-cis conformation in the cyclohexadiene ring in the conjugated chain. 1 has been prepared together with its 13-Z isomer in an overall yield of 0.5percent. 1 and 13-Z-1 photochemically interconvert in a clean way.In this system, only photoisomerization around the C13=C14 double bond is observed.In the photostationary state, the 13-Z isomer is predominant.All-E-12-ethyl-19-methylretinal (2) and all-E-12-ethylretinal (3) were prepared in good overall yields (20percent and 30percent) from β-ionone using the novel synthon, 3-methyl-4-(diethylphosphono)-2-hexenenitrile (11).The photochemistry of these retinal derivatives is very similar to that of retinal.The 9-Z, 11-Z and 13Z isomers of 2 and 3 were photochemically prepared.The 13C NMR spectra of these new compounds gave information about the structural elements of alkyl groups in conjugated systems and about the conformation of the conjugated chain.