62680-14-2

Usage

Uses

Used in Organic Synthesis:
2,5-Cyclohexadiene-1-carboxylic acid, 1-methyl-4-oxo-, methyl ester is used as a starting material in organic synthesis for the preparation of various complex molecules. Its reactivity and functional groups make it a valuable intermediate in the synthesis of a wide range of organic compounds.
Used in Pharmaceutical Industry:
2,5-Cyclohexadiene-1-carboxylic acid, 1-methyl-4-oxo-, methyl ester is used as a building block in the preparation of various pharmaceuticals. Its structural features allow for the development of new drugs with potential therapeutic applications.
Used in Fragrance and Flavoring Industry:
2,5-Cyclohexadiene-1-carboxylic acid, 1-methyl-4-oxo-, methyl ester is used in the production of fragrances and flavorings due to its aromatic properties. Its unique scent and taste characteristics make it a valuable ingredient in the creation of various consumer products.
Used in Dye and Pigment Manufacturing:
2,5-Cyclohexadiene-1-carboxylic acid, 1-methyl-4-oxo-, methyl ester is used in the manufacture of dyes and pigments, where its color properties are harnessed to produce a variety of colored compounds for use in different industries.
Used in Medical Research:
2,5-Cyclohexadiene-1-carboxylic acid, 1-methyl-4-oxo-, methyl ester has potential applications in the field of medicine, particularly in the development of new drugs for the treatment of various diseases and conditions. Its chemical properties and reactivity make it a promising candidate for further research and development in pharmaceutical applications.

Upstream product

• 67-56-1 methanol 
• 62680-12-0 trans-1-Methoxy-4-phenylsebnobut-1-en-3-on 
• 920-46-7 Methacryloyl chloride 
• 59034-54-7 1-methyl-cyclohexa-2,5-dienecarboxylic acid methyl ester 
• 64299-67-8 Methyl-2-Phenylsulfinylmethylenpropionat 
• 59414-23-2 1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene 

Downstream Products

• 73505-48-3 methyl 3-hydroxy-6-methylbenzoate 

Relevant academic research and scientific papers

1,4-Cyclohexadienes as mechanistic probes for the Jacobsen epoxidation: Evidence for radical pathways

1,4-Cyclohexadienes allow a direct comparison of epoxidation and C-H oxidation within the same molecule and give evidence for radical pathways during the Jacobsen epoxidation. The Royal Society of Chemistry 2005.

Stereoselectivity control by oxaspiro rings during Diels-Alder cycloadditions to cross-conjugated cyclohexadienones: The syn oxygen phenomenon

The diastereofacial selectivity operating in Diels-Alder additions involving spirocyclic cross-conjugated cyclohexadienones with dienes of varying reactivity has been investigated. The study has included the ether series 1a-c as well as the lactone/ketone pair 2a/2b. In all cases, the preferred [4+2] cycloaddition pathway consisted of bonding from that π-surface syn to the oxygen atom. 4-Substituted-4-methyl-2,5-cyclohexadienones (monocyclic systems) were also examined and found to undergo bond formation preferentially from the face bearing the more electron-withdrawing of the two groups at the 4 position. Kinetic parameters were determined for the cycloaddition of 1a and 2a to cyclopentadiene. The rate acceleration profile of solvents was in the order CF3CH2OH ? CH3CN～CH2Cl 2 for the production of 9a from 1a and CF3CH2OH ? CH2Cl2 > CH3CN for the production of 21a from 2a, respectively. This spread in polarity had no major impact on product distribution, a phenomenon also reflected in the behavior of 4-substituted-4-methyl-2,5-cyclohexadienones under comparable conditions. Theoretical assessment of these experimental facts was undertaken at the HF/6-31G* level. The facial selectivity is understandable in terms of the secondary interaction between the HOMO of the diene and LUMO of the dienophile as well as the effective hyperconjugation between the newly forming bond and the 4-anti-C-C σ-orbital due to the more electron-donating bond, as defined by the Cieplak model.

ON THE USE OF beta PHENYLSULFINYL- alpha , beta -UNSATURATED CARBONYL DIENEOPHILES IN DIELS-ALDER REACTIONS.

The use of beta -phenylsulfinyl- alpha , beta -unsaturted carbonyl dieneophiles as synthetic equivalents of alpha , beta -ethynyl carbonyl systems has been demonstrated. The sulfoxides were prepared by oxidation of the sulfides, which in turn were obtained from the beta -dicarbonyl systems by standard methods. A key feature of the scheme is that the phenylsulfinyl group does not compete with the carbonyl function in determining the regiochemistry of cycloaddition with the highly nucleophilic trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene. Application of the methodology to the synthesis of the disodium prephenate dimethyl acetals is described.