31689-38-0

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Cyclohexadiene-1-carboxylic acid, 1-ethylis used as a starting material for the synthesis of various pharmaceuticals. Its unique structure and reactivity contribute to the development of new drugs with potential therapeutic applications.
Used in Agricultural Chemicals Industry:
2,5-Cyclohexadiene-1-carboxylic acid, 1-ethylalso serves as a building block in the synthesis of agricultural chemicals, where it is used to create new compounds with pesticidal or herbicidal properties, enhancing crop protection and yield.
Used in Medicinal Chemistry and Drug Development:
Due to its structural features and reactivity, 2,5-Cyclohexadiene-1-carboxylic acid, 1-ethylhas potential applications in the field of medicinal chemistry. It can be utilized in the design and synthesis of novel compounds with potential therapeutic effects, contributing to drug discovery and development processes.

Upstream product

• 74-96-4 ethyl bromide 
• 65-85-0 benzoic acid 
• 4794-04-1 1,4-dihydrobenzoic acid 
• 75-03-6 ethyl iodide 

Downstream Products

• 2025-56-1 ethyl radical 
• 100-41-4 ethylbenzene 
• 1334440-33-3 5-ethyl-1,2-dihydro-1,1'-biphenyl 
• 1263292-16-5 (1-ethyl-cyclohexa-2,5-dienyl)methanol 

Relevant academic research and scientific papers

Catalytic Enantioselective Birch–Heck Sequence for the Synthesis of Phenanthridinone Derivatives with an All-Carbon Quaternary Stereocenter

Novel phenanthridinone analogues with an all-carbon quaternary stereocenter have been enantioselectively synthesized using the Birch–Heck sequence. Flat phenanthridinone structures have extensive bioactivity but consequently also suffer from poor therapeutic selectivity. The addition of a quaternary center to the phenanthridinone skeleton has the potential to generate more complex analogues with improved selectivity. Unfortunately, no general synthetic pathway to such derivatives exists. Herein we report a four-step process that transforms inexpensive benzoic acid into 22 different quaternary carbon-containing phenanthridinone analogues with a variety of substituents on all three rings: alkyl groups at the quaternary center; methyl, methoxymethyl, or para-methoxybenzyl on the amide nitrogen; and halogen and methyl substituents on the aryl ring. Good to very good enantioselectivity was demonstrated in the key intramolecular desymmetrizing Mizoroki–Heck reaction. Transformations of the Heck reaction products into molecules with potentially greater therapeutic relevance were also accomplished.

Diastereoselective hydroformylation of 2,5-cyclohexadienyl-1-carbinols with catalytic amounts of a reversibly bound directing group

A phosphinite plays a role as a reversibly bound directing group for the regio-and diastereoselective hydroformylation of 2,5-cyclohexadienyl-1- carbinols. Of the two alkene functions only one was functionalized through hydroformylation to form a syntheti

Simple two-step ipso substitution of aromatic carboxylic acids by alkyl halides

Methyl-substituted arenes can be synthesized with high regioselectivity in only two steps through formal exchange of an aromatic carboxylic acid function with an alkyl substituent. The results obtained with toluic acid illustrate that good to very good yields can be obtained from inexpensive reagents (see scheme).

Homolytic dissociation of 1-substituted cyclohexa-2,5-diene-1-carboxylic acids: An EPR spectroscopic study of chain propagation

Hydrogen abstraction from 1-substituted cyclohexa-2,5-diene-1-carboxylic acids containing linear, branched and cyclic alkyl substituents, as well as allyl, propargyl (prop-2-ynyl), cyanomethyl and benzyl substituents, has been studied by EPR spectroscopy. For each carboxylic acid, EPR spectra of the corresponding cyclohexadienyl radicals were observed at lower temperatures, followed by spectra due to ejected carbon-centred radicals at higher temperatures. Rate constants, for release of the carbon-centred radicals from the cyclohexadienyl radicals, were determined from radical concentration measurements for the above range of substituents. The rate of cyclohexadienyl radical dissociation increased with branching in the 1-alkyl substituent and with electron delocalisation in the ejected carbon-centred radical; 3,5-and 2,6-dimethyl-substitution of the cyclohexadienyl ring led to reductions in the dissociation rate constants. Rate data for abstraction of bisallylic hydrogens from the cyclohexadienyl acids were also obtained for ethyl, n-propyl and isopropyl radicals. These results indicated a sharp drop in the rate of hydrogen abstraction as the degree of branching in the attacking radical increased. Small decreases in the hydrogen abstraction rate constants were observed for cyclohexadienes containing CO2R substituents.

Unique carbon-carbon bond homolysis in 3-alkylcyclohexa-1,4-dienyl-3-carboxylic acid radicals

3-Substituted cyclohexadienyl radicals generated by hydrogen abstraction from 3-alkylcyclohexa-1,4-diene-3-carboxylic acids readily fragment to produce alkyl radicals and benzoic acid; suitably functionalised alkyl groups cyclize in moderate yields.