57006-69-6

Usage

Uses

Used in Chemical Synthesis:
Acetic acid (2E,4E)-2,4-hexadienyl ester is used as a key intermediate in regioselective cycloadditions with a variety of dienophiles. Its unique (2E,4E)-hexa-2,4-dienyl ester functional group allows for selective reactions, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pheromone Production:
Acetic acid (2E,4E)-2,4-hexadienyl ester is used as a sex pheromone in various insect species, particularly in the Heteroptera order. Its ability to attract and stimulate mating behavior in these insects makes it an important component in pest control and monitoring programs.
Used in Defense Secretions:
In addition to its role as a sex pheromone, Acetic acid (2E,4E)-2,4-hexadienyl ester is also found in the defense secretions of Thaumastella spp. Its presence in these secretions suggests that it may have defensive properties, such as repelling predators or deterring attacks from other organisms.
Overall, Acetic acid (2E,4E)-2,4-hexadienyl ester is a versatile compound with a range of applications in chemical synthesis, pheromone production, and defense secretions. Its unique chemical structure and natural occurrence make it an interesting target for further research and development in these fields.

Upstream product

• 110-44-1 sorbic Acid 
• 108-24-7 acetic anhydride 
• 689-89-4 (2E,4E)-methylhexa-2,4-dienoate 
• 17102-64-6 Sorbyl alcohol 
• 114988-53-3 1-acetoxy-3-acetoxymethoxy-4-hexene, E isomer 
• 127-09-3 sodium acetate 
• 80639-18-5 (E)-1,4-hexadien-3-yl acetate 
• 91001-07-9 (E)-hexa-1,4-dien-3-ol 
• 114988-54-4 4-propenyl-1,3-dioxane, E-isomer 
• 108965-77-1 (E)-(2S,3S)-2-Hydroxy-3-trimethylsilanyl-hex-4-enoic acid methyl ester 
• 114628-86-3 1,3-diacetoxy-4-hexene 

Downstream Products

• 33956-49-9 (8E,10E)-dodeca-8,10-dienol 
• 70729-06-5 [Bis-(4-methoxy-phenyl)-methyl]-((2E,4E)-hexa-2,4-dienyl)-amine 
• 70729-07-6 [Bis-(4-methoxy-phenyl)-methyl]-bis-((2E,4E)-hexa-2,4-dienyl)-amine 
• 533-18-6 2-methylphenyl acetate 
• 115270-12-7 1-<(tert-butoxycarbonyl)amino>-2(E),4(E)-hexadiene 
• 112-30-1 1-Decanol 
• 7735-43-5 1,20-eicosanediol 
• 68252-11-9 trans,trans-hexadeca-12,14-dien-1-ol 
• 111-28-4 hexa-2,4-dienyl alcohol 
• 37935-49-2 (8E,10E)-8,10-Dodecadienyl-(tetrahydro-2-pyranyl)ether 
• 105273-54-9 1-((E)-1-Vinyl-but-2-enyl)-cyclohexanol 
• 105273-55-0 ((2E,4E)-1-Hexa-2,4-dienyl)-cyclohexanol 
• 105273-53-8 1-((E)-1-Methyl-penta-2,4-dienyl)-cyclohexanol 

Relevant academic research and scientific papers

Synthesis method of laspeyresia pomonella sex pheromone

The invention relates to a synthesis method of laspeyresi pomonella sex pheromone. The method comprises the steps as follows: (1) methanol is added to methyl sorbate as a raw material, and an intermediate A sorbic alcohol is obtained through 5% palladium-carbon catalytic hydrogenation reduction; (2) the intermediate A sorbitol obtained in (1) and acetic anhydride are subjected to a reaction in ethyl acetate, triethylamine and water to obtain an intermediate B sorbic acetate; (3) 6-chlorohexanol is subjected to a reaction with trimethylchlorosilane in toluene in the presence of ethyl acetate and triethylamine, after the reaction, water is added, stirring and layering are performed, and an intermediate C6-chlorohexanol trimethylsilyl ester is obtained; (4) the intermediate B sorbic acetate and the intermediate C6-chlorohexanol trimethylsilyl ester are subjected to a reaction with sodium sand in a toluene solution, then, water and sulfuric acid are dropwise added, layering and rectification are performed, and a target product E8,E10-dodecadiene-1-ol is obtained. The synthesis method has the advantages as follows: the laspeyresi pomonella sex pheromone is synthesized from available rawmaterials, the reaction route is short, and the selectivity and product yield can be increased.

Methods and compositions for terpenoid tricycloalkane synthesis

In one aspect, the disclosure relates to methods for preparation of intermediates useful for the preparation of terpenoid cores. In a further aspect, the disclosed methods pertain to the preparation of compounds comprising a terpenoid core or scaffold, su

An Enyne Cope Rearrangement Enables Polycycloalkane Synthesis from Readily Available Starting Materials

Cyclohexanone-derived Knoevenagel adducts (cyclohexylidenemalononitriles) and two different propargyl electrophiles serve as carbon sources for assembling diverse 6/7/5 tricycloalkanes, a common terpenoid framework. The sequence involves three unique reac

Eleuthesides and their analogs: VII. Synthesis of menthane derivatives by the Diels-Alder reaction of levoglucosenone with (2E,4E)-hexa-2,4-dien-1-yl acetate

The Diels-Alder reaction of levoglucosenone with (2E,4E)-hexa-2,4-dien-1-yl acetate was used to synthesize chiral functionalized derivatives of isopropyl(methyl)cyclohexene fused to a carbohydrate fragment.

Chiral gold complex-catalyzed hetero-diels-alder reaction of diazenes: Highly enantioselective and general for dienes

A chiral gold(I) complex-catalyzed highly regio- and enantioselective azo hetero-Diels-Alder reaction has been developed. The chiral gold(I) complex acting as a Lewis acid exhibits high efficiency in the activation of urea-based diazene dienophiles. Moreover, this chiral gold catalyst also rendered a cascade intramolecular enyne cycloisomerization/asymmetric azo-HDA reaction.

Cobalt-catalyzed reductive allylation of alkyl halides with allylic acetates or carbonates

An efficient method for the direct allylation of alkyl halides catalyzed by simple cobalt(II) bromide has been developed. This reaction, using a variety of substituted allylic acetates or carbonates, provides the linear product as the major product. It displays broad substrate scope and good functional group tolerance. Copyright

Sequential catalytic isomerization and allylic substitution. Conversion of racemic branched allylic carbonates to enantioenriched allylic substitution products

A catalytic protocol for the conversion of readily accessible racemic, branched aromatic allylic esters to branched allylic amines, ethers, and alkyls has been developed. Palladium-catalyzed isomerization of branched allylic esters to terminal allylic esters, followed by sequential iridium-catalyzed allylic substitution, gave the branched allylic products in good yield with high regioisomeric and enantiomeric selectivity. Both electron-rich and electron-poor branched allylic esters gave products in >90% ee. High enantiomeric excesses were also observed for the products from the reactions of 2-thienyl acetates and dienyl carbonates. Copyright

Synthesis of dodeca-8E,10E-dien-1-ol - The sex pheromone of Laspeyresia pomonella via the acetolysis of 4-propenyl-1,3-dioxane

A new scheme has been developed for the synthesis of dodeca-8E,10E-dien-1-ol (the sex pheromone of the codling moth) from sorbyl acetate, available from 4-propenyl-1,3-dioxane through the intermediate diacetate of 3-propenyl-2-oxapentane-1,5-diol.

Reactivity of Lysine Moieties toward γ-Hydroxy-α,β-unsaturated Epoxides: A Model Study on Protein-Lipid Oxidation Product Interaction

Epoxyols are generally accepted as crucial intermediates in lipid oxidation. The reactivity of γ-hydroxy-α,β-unsaturated epoxides toward lysine moieties is investigated, employing trans-4,5-epoxytrans-2-hexen-1-ol (EH) as a model substrate and propylamine or N2-acetyl-L-lysine 4-methylcoumar-7-ylamide (AcLys-MCA) as model reagents for protein-bound lysine. Independent syntheses are reported for EH and AcLys-MCA. Reaction of the amine components with EH in THF yields 4-(propylamino)-trans-2-hexene-1,5-diol and N2-acetyl-N6-(1,5-dihydroxy-trans-2-hexen-4-yl)-L-lysine 4-methylcoumaryl-7-amide, respectively. Unequivocal structural characterization of the products prove the epoxy ring cleavage to proceed by a true SN2 mechanism. Incubation of EH with propylamine and AcLys-MCA in aqueous medium at 37 °C shows the turnover to decrease with lower pHs. From reaction of EH (100 mM) with AcLys-MCA (50 mM) under physiological conditions (pH 7.4), 3% of the lysine moieties can be identified in the form of N2-acetyl-N6-(1,5-dihydroxy-trans-2-hexen-4-yl)-L-lysine 4-methylcoumar-7-ylamide after 24 h.