106140-63-0Relevant academic research and scientific papers
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.
Retinoids. 6. Preparation of alkyl- and trimethylsilyl-substituted retinoids via conjugate addition of cuprates to acetylenic esters
Ernst, Ludger,Hopf, Henning,Krause, Norbert
, p. 398 - 405 (2007/10/02)
Five retinoids bearing the ethyl, tert-butyl, and trimethylsilyl groups in the 9-position of retinal and the ethyl and tert-butyl groups in the 13-position have been synthesized. The key step of the syntheses involves the conjugate addition of lithium die
