81714-81-0

Basic information

• Product Name: 2,4,6-Heptatrienoic acid, 3-methyl-7-phenyl-, (2Z,4E,6E)-
• CAS NO: 81714-81-0
• Molecular Formula: C14H14O2
• Molecular Weight: 214.264
• Mol File: 81714-81-0.mol

Chemical Properties

• CAS DataBase Reference: 2,4,6-Heptatrienoic acid, 3-methyl-7-phenyl-, (2Z,4E,6E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Heptatrienoic acid, 3-methyl-7-phenyl-, (2Z,4E,6E)-(81714-81-0)
• EPA Substance Registry System: 2,4,6-Heptatrienoic acid, 3-methyl-7-phenyl-, (2Z,4E,6E)-(81714-81-0)

Safety Data

• Hazardous Substances Data: 81714-81-0(Hazardous Substances Data)

Upstream product

• 134641-64-8 5,6-Dihydro-4-methyl-6-(2-phenylethenyl)-2H-pyran-2-one 
• 30288-18-7 (Z)-3-methyl-2,4-pentadienoic acid 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 14371-10-9 (E)-3-phenylpropenal 
• 4173-44-8 (E,E)-6-phenyl-3,5-hexadien-2-one 
• 96-32-2 bromoacetic acid methyl ester 
• 19041-17-9 methyl 4-bromo-3-methylbut-2-enoate 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 286372-74-5 4-methyl-6-styryl-5,6-dihydro-2H-pyran-2-ol 
• 42599-24-6 E-styryl iodide 

Downstream Products

• 64245-74-5 3-methyl-7t-phenyl-hepta-2t,4t,6-trienoic acid 

Relevant articles and documents

An Efficient Synthesis of Conjugated Trienoic Acids via Stille Cross Coupling Reaction of (E)-1,2-Bis(tributylstannyl)ethylene

Stereoselective construction of conjugated trienoic acids was achieved through two successive Stille reactions, coupling as the first step (E)-1,2-bis(tributylstannyl)ethylene and tributylstannyl-3-iodoalk-2-enoates. The second step can be conducted by two different routes: 1) cross-coupling of the stannyldienoic acid reagents 2 and vinyliodides or 2) cross-coupling of vinyltin reagents and tributylstannyl 5-iodopenta-2,4-dienoates generated by iododestannylation of stannyldienes 2.

A general synthesis of (2Z)-terpenoic acids

A three-step synthesis of (2Z), (4E)-polyenic acids 6 is described. Condensation of aldehydes 1 with potassium prenal enolate led to dihydropyranols 3 which were oxidized into dihydropyrones 5, precursors of (2Z), (4E)-polyenic acids 6. The procedure was applied to a synthesis of 13- cis-retinoic acids from β-ionylidene acetaldehydes. (C) 2000 Elsevier Science Ltd.

Palladium-Catalyzed Syntheses of Conjugated Polyenes

Conjugated trienes have been prepared by the palladium-catalyzed reaction of vinylic bromides with 2,4-pentadienoic acid and its 3-methyl derivative, in the presence of triethylamine.Methyl (E)-3-bromo-2-methylpropenoate also forms conjugated trienes and in some instances also tetraenes when it is reacted with 1,3-dienes under similar conditions.Some loss of stereochemistry in the starting vinylic bromide or, more often, in the diene may occur in the rections presumably because equilibrating ?-allylic intermediates are involved.1,3,5-Hexatriene and 2 equiv of methyl (E)-3-bromo-3-methylpropenoate form orange-red dimethyl (E,E,E,E,E)-2,11-dimethyl-2,4,6,8,10-dodecapentaenedioate in modest yield.