183808-75-5

Usage

Uses

Used in Organic Chemistry:
2,5-Cyclohexadiene-1-carboxylic acid, 1-[2-(2-cyclohexen-1-yloxy)ethyl]is used as a building block for the synthesis of various organic compounds. Its cyclohexadiene and cyclohexenyloxyethyl moieties provide opportunities for further functionalization and the creation of novel organic molecules with specific properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2,5-Cyclohexadiene-1-carboxylic acid, 1-[2-(2-cyclohexen-1-yloxy)ethyl]may be utilized as a precursor for the development of pharmaceutical agents. Its unique structure could be exploited to design new drugs with improved pharmacological profiles, such as enhanced potency, selectivity, or bioavailability.
Used in Chemical Research:
2,5-Cyclohexadiene-1-carboxylic acid, 1-[2-(2-cyclohexen-1-yloxy)ethyl]can also be employed as a research tool in chemical studies. Its distinct molecular architecture allows for investigations into the reactivity, stability, and interactions of similar compounds, contributing to a deeper understanding of organic and medicinal chemistry principles.

Upstream product

• 65-85-0 benzoic acid 
• 183808-73-3 3-(2-iodoethoxy)cyclohex-1-ene 
• 211365-70-7 2-(cyclohex-2-en-1-yloxy)ethyl-4-methylbenzenesulfonate 
• 90112-73-5 3-(2-hydroxyethoxy)cyclohexene 
• 1521-51-3 rac-3-bromocyclohexene 

Downstream Products

• 10198-29-5 perhydrobenzo[b]furan 

Relevant academic research and scientific papers

Reductive free-radical alkylations and cyclisations mediated by 1-alkylcyclohexa-2,5-diene-1-carboxylic acids

A range of 1-alkylcyclohexa-2,5-diene-1-carboxylic acids were prepared by Birch reduction-alkylation of benzoic acid and their efficiency as mediators of alkyl radical chain addition and cyclisation processes was investigated. Reductive alkylations were respectably successful, even with only one or two equivalents of alkene, for secondary, tertiary and benzylic radicals. Reaction of 1-[2-(cyclohex-2-enyloxy)ethyl]cyclohexa-2,5-diene-1-carboxylic acid yielded the product of exo-trig-cyclisation, i.e. 7-oxabicyclo[4.3.0]nonane, in a yield comparable to that obtained from the tributyltin hydride induced cyclisation of 3-(2′-iodoethoxy)-cyclohexene. This, together with the isolation of both exo- and endo-cyclisation products from 1-[2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethoxy)ethyl]cyclohexa-2,5-diene- 1-carboxylic acid established that ring closures could also be satisfactorily mediated with these reagents. Preparations were completely free of metal contaminants and direct reduction of the alkyl radicals, prior to addition or cyclisation, was completely absent. However, the desired products were accompanied by alkylbenzenes, together with by-products from the initiator decompositions, and this complicated work-up. Failure to obtain 1-[2-(prop-2-yn-1-yloxy)cyclohexyl]cyclohexa-2,5-diene-1-carboxylic acid in Birch reductive alkylations with trans-1-iodo-2-(prop-2-yn-1-yloxy)cyclohexane (and the corresponding bromide) indicated a limitation on precursor synthesis. The Birch reduction-alkylation was not of universal applicability and was suppressed for alkyl halides having β-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.