3731-95-1

Usage

Uses

Used in Organic Synthesis:
2,5-Cyclohexadiene-1,4-dione, 2-(2-propenyl)is used as a precursor in the synthesis of various organic compounds, providing a foundation for the creation of a wide range of chemical products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2,5-Cyclohexadiene-1,4-dione, 2-(2-propenyl)is utilized as a reagent in organic reactions, contributing to the development of new drugs and medicinal compounds.
Used in Dye Manufacturing:
2,5-Cyclohexadiene-1,4-dione, 2-(2-propenyl)is also used in the production of dyes, where its chemical properties contribute to the color and stability of the final product.
Used in Industrial Product Development:
2,5-Cyclohexadiene-1,4-dione, 2-(2-propenyl)is employed in the development of other industrial products, leveraging its chemical properties to enhance the performance or characteristics of these products.
Used as a Chemical Intermediate in Polymer Production:
In the manufacturing of polymers and other materials, 2,5-Cyclohexadiene-1,4-dione, 2-(2-propenyl)serves as a valuable chemical intermediate, playing a crucial role in the formation of complex polymer structures.

Upstream product

• 35736-25-5 3-(2-hydroxy-5-aminophenyl)-1-propene 
• 5721-21-1 2-allylhydroquinone 
• 60316-51-0 2-bromo-1,1,4,4-tetramethoxycyclohexa-2,5-diene 
• 106-95-6 allyl bromide 
• 584-82-7 2-allyl-4-methoxyphenol 
• 1745-81-9 o-Allylphenol 
• 106-51-4 p-benzoquinone 
• 305-80-6 4-diazobenzenesulfonic acid 

Downstream Products

• 182014-91-1 2-(1-propenyl) tetracyanoquinodimethane 

Relevant academic research and scientific papers

Total synthesis of the novel, biologically active epoxyquinone dimer (±)-torreyanic acid: A biomimetic approach

(Chemical Equation Presented) A total synthesis of the complex, biologically active, dimeric natural product (±)-torreyanic acid, which is composed of seven rings and laced with dense, variegated oxy- functionalization, has been accomplished from readily available allyl-substituted p-benzoquinone 8. Our synthetic stratagem involves crafting an epoxyquinone monomer for use in a biomimetic cascade process involving tandem a 6π electrocyclization and a Diels-Alder dimerization.

Access to functionalized quinones via the aromatic oxidation of phenols bearing an alcohol or olefinic function catalyzed by supported iron phthalocyanine

The controlled oxidation at only one position of compounds with several oxidizable sites, while keeping the other sites intact, has been demonstrated for phenols bearing alcohol or olefinic functional groups. Iron tetrasulfophthalocyanine supported on silica was found to be an efficient catalyst for the preparation of functionalized quinones under mild conditions, with tert-butylhydroperoxide as the oxidant. A novel rapid and mild one-pot procedure for the covalent grafting of iron tetrasulfophthalocyanine onto silica has been developed. The supported catalyst was characterized by chemical analysis, a specific surface study, UV-vis spectroscopy and XPS. A non-radical mechanism for this unusual selective oxidation has been revealed by 18O labelling experiments. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Allylation of quinones bu allylic indium reagents

Allylation of a variety of quinones by allylic indium sesquihalides was studied.Reactions of unsubstituted p-benzoquinone with allylindium, prenylindium, and geranylindium reagents gave, after oxidation with silver oxide, the corresponding allylated quinones in good yields.These reactions appear to proceed via 1,2-addition of the allylic indium reagents at the γ-carbon followed by sigmatropic rearrangement.Substituted quinones reacted with allylindium reagent giving excellent yields of allylquinols, whereas with prenylindium and geranylindium reagents, trisubstituted quinones gave diprenylcyclohexene-1,4-diones and 2,3-disubstituted quinones gave mixtures of prnylhydroquinones and diprenylcyclohexene-1,4-diones.In the prenylation of haloquinones, 1,2-addition, sigmatropic rearrangement, and elimination of indium(III) halide occurred in sequence yielding prenylquinones. 2-Hydroxy- and 2-methoxy-1,4-naphthoquinones gave α-addition products with prenylindium and cinnamylindium reagents.

Allylation of Quinones with Allyltin Reagents

Lewis acid (BF3) catalyzed allylation of quinones with allyl- (2a), 2-methyl-2-propenyl- (2b), trans-2-butenyl- (2c,d), 3-methyl-2-butenyl- (2e,f), and trans-cinnamyltrialkyltin (2g) gives the corresponding allylhydroquinones with high regioselectivity.Vitamin K2(5) (7) and coenzyme Q1 (9) were prepared in yields of 78 and 75percent, respectively.These reactions appear to proceed through allylquinol intermediates which undergo rearrangement under the influence of BF3.The success of this synthesis of vitamin K2(5) and coenzyme Q1 depends on the fact that the reaction of 3-methyl-2-butenyltin with quinones occurs at the α carbon of the allylic system.

Organocopper Chemistry of Quinone Bisketals. Application to the Synthaais of Isoprenoid Quinone Systems

The reactions of organocuprates of 1,4-benzoquinone and 1,4-naphthoquinone bisketals are reported.These reagents, formed from the corresponding lithium reagent, cuprous iodide, and dimethyl sulfide react efficiently with allylic bromides (allyl, prenyl, geranyl, and phytyl), often with utilization of greater than one R group of the R2CuLi.Their reactions with acid chlorides and benzyl bromide proceed with acceptable efficiency, but they are unreactive toward a number of other substrates.The utility of this chemistry in the synthesis of menaquinone-2, phylloquinone,cymopol, and cymopol methyl ether is described.