68826-40-4

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 65562-83-6 2,7,11-trimethyl-dodeca-4,6,10-trien-3-one 
• 14505-74-9 α-cyclocitral 
• 80922-54-9 (E)-3-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-propensaeure-ethylester 
• 14393-45-4 (E)-3-(2,6,6-trimethylcyclohex-1-enyl)acrylic acid 
• 72172-57-7 (E)-2,7-dimethyl-2,6-octadienal 
• 597-04-6 ethyl 2,2-dimethyl-3-oxobutanoate 
• 920-39-8 isopropylmagnesium bromide 
• 141208-06-2 (2E)-N-methoxy-N-methyl-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenamide 

Relevant academic research and scientific papers

4,5-Didehydro-9-demethyl-9-halo-5,6-dihydroretinals and their 9-cyclopropyl and 9-isopropyl derivatives - Simple preparation of α-ionone derivatives and pure (all-E)-, (9Z)- and (11Z)-α-retinals

α-Ionone and several of its chemically modified derivatives have been prepared in high yield in full isomeric purity by a Wadsworth-Emmons procedure using imino-phosphonate anion reagents. Starting from α-ionone, 5-(2′,6′,6′-trimethylcyclo-2′-hexen-1′-yl) -4-penten-2-yn-1-al could be prepared in a high yielding one-pot procedure. The corresponding (9-Cl-, 9-Br- and 9-I-α-ionylidene)acetaldehyde system could be obtained in one step in a quantitative mixture of (9Z) and (all-E) isomers by 1,4-nucleophilic addition reactions. The pure (all-E) and (9Z) isomers could be separated by simple column chromatography. The corresponding [(9Z)- and (all-E)-9-demethyl-9-fluoro-α-ionylidene]acetaldehydes could also be obtained in pure form by simple column chromatography. These α-ionylidene systems could be easily converted either into the (all-E)-4,5-didehydro-9- demethyl-9-halo-5,6-dihydroretinals or the corresponding (9Z) isomers in two steps. Similar mixtures of the corresponding (9Z,11Z)-and (9Z)-nitriles could be obtained by normal chemistry. The (9Z,11Z) isomer is the main component of this mixture, and could be obtained in pure form. Subsequent reduction with DIBAL-H and careful workup gave the pure (9Z,11Z)-9-halo-retinals. These (9Z,11Z) isomers show a similar extreme acid sensitivity to the corresponding 9-halo-β-retinals. α-Retinal and its 9-demethyl, 19,19-ethano and 19,19-dimethyl derivatives have been prepared in the (all-E), (9Z), and (11Z) isomeric forms in a similar manner. The corresponding β-retinal and its 9-demethyl derivative in the various isomeric forms are known. In this paper the 19,19-ethano- and 19,19-dimethyl-β-retinals in the (all-E), (9Z), and (11Z) isomeric forms are also reported. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Synthesis of olivacene, a constituent of Archilejeunea olivacea

A simple synthesis of olivacene 1, a naturally occurring sesquiterpenoid hydrocarbon isolated from Archilejeunea olivacea has been described.

Retinoids and related compounds. Part 22. Synthesis of β-ionone analog tricarbonyliron complexes

The synthesis of β-ionone analog tricarbonyliron complexes was investigated. N-Methoxy-N-methyl-(2,6,6-trimethyl-1-clohexen-1-yl)-2- propenamide (Weinreb amide), prepared from the corresponding ethyl ester and N,O-dimethylhydroxylamine hydrochloride, reacted smoothly with various organometallic reagents to afford the β-ionone analogs in good to excellent yields. Treatment of these compounds with dodecacarbonyltriiron afforded the corresponding tricarbonyliron complexes in high yields.