66876-03-7

Basic information

• Product Name: 2,4-Pentadienal, 5-cyclohexyl-, (E,E)-
• CAS NO: 66876-03-7
• Molecular Formula: C11H16O
• Molecular Weight: 164.247
• Mol File: 66876-03-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2,4-Pentadienal, 5-cyclohexyl-, (E,E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Pentadienal, 5-cyclohexyl-, (E,E)-(66876-03-7)
• EPA Substance Registry System: 2,4-Pentadienal, 5-cyclohexyl-, (E,E)-(66876-03-7)

Safety Data

• Hazardous Substances Data: 66876-03-7(Hazardous Substances Data)

Upstream product

• 110905-37-8 (E)-(4-Oxo-2-butenyl)phosphonsaeure-diethylester 
• 2043-61-0 cyclohexanecarbaldehyde 
• 129422-73-7 (5-aza-5-cyclohexylpenta-2,4-dienyl)diethoxyphosphin-1-one 
• 2798-73-4 (Z)-1-methoxybut-1-en-3-yne 

Downstream Products

• 1175039-36-7 (S,5Z,7E)-8-cyclohexylocta-1,5,7-trien-4-ol 
• 147217-70-7 (2E,4E,6E,8E,10E,12E)-13-Cyclohexyl-trideca-2,4,6,8,10,12-hexaenal 
• 147217-69-4 (2E,4E,6E,8E,10E)-11-Cyclohexyl-undeca-2,4,6,8,10-pentaenal 
• 147217-68-3 (2E,4E,6E)-7-Cyclohexyl-hepta-2,4,6-trienal 
• 76080-85-8 (2E,4E,6E,8E)-9-Cyclohexyl-nona-2,4,6,8-tetraenal 

Relevant articles and documents

Catalytic enantioselective allylation of dienals through the intermediacy of unsaturated π-allyl complexes

(Chemical Equation Presented) The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester [allylB(pin)] to >,β,γ,δ-unsaturated aldehydes is described. This reaction results in a remarkable inversion of substrate olefin geometry, providing the Z,E-configured reaction product in good enantioselectivity and olefin stereoselectivity. The reaction appears to proceed by conversion of the dienal to an unsaturated B-allyl complex followed by reductive elimination via transition state II. Enantioselectivities range from 73-94% ee for a range of δ-substituted dienals when chiral ligand L3 is employed.

AgAsF6 as safe alternative to AgClO4 for generating cationic zirconocene species: Utilities in Lewis acid-promoted selective C---C bond forming reactions

For generating cationic zirconocene species that are useful for organic synthesis, AgAsF6 proved to be an efficient catalyst that serves as a safe alternative to AgClO4. Scope and limitation is discussed on this new catalyst in the processes including (1) alkyl/alkenyl transfer reaction from organozirconocene chloride to aldehyde, (2) two- and four-carbon homologation of aldehyde, (3) dual synthetic methods of 1,3-dienes from aldehydes/ketones via 1,3-bimetallic species, and (4) three-component alkylative cycloaddition via o-quinodimethane species.

New Functionalized Horner-Wadsworth-Emmons Reagents: Useful Building Blocks in the Synthesis of Polyunsaturated Aldehydes. A Short Synthesis of (+/-)-(E,E)-Coriolic Acid

The new Horner-Wadsworth-Emmons reagents 4 and 5 transform carbonyl compounds into 2,4-pentadienals and 3-methyl-2,4-pentadienals, respectively.Reagent 4 gives good yields of the desired products with a variety of aldehydes and ketones; reagent 5 generally gives good yields with aldehydes, but gives lower yields with ketones.The reactions proceed under mild conditions and give the products as predominantly 2E,4E isomers, with moderate to good stereoselectivity.In general, pure samples of the 2E,4E-dienals can be obtained after chromatography.Reagents 4 have been used in the key step in a short synthesis of (+/-)-13-hydroxy-9(E),11(E)-octadecanoic acid ((E,E)-coriolic aicd, 45).