1560-11-8

Usage

Uses

1. Used in Pharmaceutical Applications:
1-Cyclopentenecarboxylic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its application in this industry is due to its ability to participate in enantioselective 1,3-dipolar cycloadditions of diazoacetates and solid-phase synthesis of substituted indolines.
2. Used in Organic Chemistry:
1-Cyclopentenecarboxylic acid is used as a reactant in the synthesis of various organic compounds, such as cis-8-hexahydroindanecarboxylic acid via Diels-Alder reaction with butadiene and in the synthesis of isoxazole derivatives. Its application in this field is attributed to its reactivity and versatility in chemical reactions.
3. Used in Antagonist Development:
1-Cyclopentenecarboxylic acid is used as a starting material for the development of antagonists for A1and A2-adenosine receptors. Its application in this area is due to its potential to modulate these receptors, which can have therapeutic implications in various conditions.
4. Used in Anticonvulsant Research:
1-Cyclopentenecarboxylic acid has been evaluated as a new effective anticonvulsant during the Anticonvulsant Screening Program (ASP) of the Antiepileptic Drug Development Program. Its application in this field is based on its potential to provide relief from seizures and improve the quality of life for patients with epilepsy.

InChI:InChI=1/C6H8O2/c7-6(8)5-3-1-2-4-5/h3H,1-2,4H2,(H,7,8)/p-1

Upstream product

• 10267-94-4 ethyl cyclopent-1-enecarboxylate 
• 16841-19-3 1-hydroxy-cyclopentanecarboxylic acid 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 26555-56-6 2-cyclopenten-1-carbonitrile 
• 51572-54-4 methyl 1-bromocyclopentanecarboxylate 
• 6140-65-4 1-cyclopentene-1-carboxaldehyde 
• 3047-38-9 cyclopent-1-enecarbonitrile 
• 857832-35-0 1-(1,2,3,4-tetrahydro-carbazol-9-yl)-cyclopentanecarboxylic acid 
• 5434-85-5 1-cyclopentene-1-carboxamide 
• 81887-89-0 2-hydroxycyclopentyl-1-carboxylic acid 
• 111-50-2 Adipic acid dichloride 
• 67886-24-2 (+/-)-cyclopent-2-enecarboxylic acid 
• 63049-47-8 6-Chlor-2-methylthio-hexansaeure 
• 67-66-3 chloroform 

Downstream Products

• 3400-45-1 cyclopentanecarboxylic acid 
• 59253-90-6 cyclopent-1-enecarbonyl chloride 
• 84257-29-4 cyclopentene-1-(N-phenyl)carboxamide 
• 91495-75-9 trans-3-phenylcyclopentanecarboxylic acid 
• 7015-25-0 (+/-)-cis-2-phenyl-cyclopentane-carboxylic acid-⁽¹⁾ 
• 57043-01-3 (+/-)-trans-2-amino-cyclopentane carboxylic acid 
• 4971-03-3 1-Jod-2-nitrocyclopentancarbonsaeure 
• 57043-00-2 (1RS,2SR)-cispentacin 
• 99343-54-1 trans-2-(benzoylthio)cyclopentanecarboxylic acid 
• 99397-53-2 cis-2-(benzoylthio)cyclopentanecarboxylic acid 
• 6694-82-2 p-nitrobenzyl cyclopentene-1-carboxylate 
• 7015-25-0 2-phenylcyclopentanecarboxylic acid 
• 110-94-1 1,5-pentanedioic acid 
• 124-04-9 Adipic acid 

Relevant academic research and scientific papers

Ligand-controlled divergent dehydrogenative reactions of carboxylic acids via C–H activation

Dehydrogenative transformations of alkyl chains to alkenes through methylene carbon-hydrogen (C–H) activation remain a substantial challenge. We report two classes of pyridine-pyridone ligands that enable divergent dehydrogenation reactions through palladium-catalyzed b-methylene C–H activation of carboxylic acids, leading to the direct syntheses of a,b-unsaturated carboxylic acids or g-alkylidene butenolides. The directed nature of this pair of reactions allows chemoselective dehydrogenation of carboxylic acids in the presence of other enolizable functionalities such as ketones, providing chemoselectivity that is not possible by means of existing carbonyl desaturation protocols. Product inhibition is overcome through ligand-promoted preferential activation of C(sp3)–H bonds rather than C(sp2)–H bonds or a sequence of dehydrogenation and vinyl C–H alkynylation. The dehydrogenation reaction is compatible with molecular oxygen as the terminal oxidant.

Macrolactam Synthesis via Ring-Closing Alkene-Alkene Cross-Coupling Reactions

Reported herein is a practical method for macrolactam synthesis via a Rh(III)-catalyzed ring closing alkene-alkene cross-coupling reaction. The reaction proceeded via a Rh-catalyzed alkenyl sp2 C-H activation process, which allows access to macrocyclic molecules of different ring sizes. Macrolactams containing a conjugated diene framework could be easily prepared in high chemoselectivities and Z,E stereoselectivities.

Palladium-Catalyzed Visible-Light-Driven Carboxylation of Aryl and Alkenyl Triflates by Using Photoredox Catalysts

A visible-light-driven carboxylation of aryl and alkenyl triflates with CO2 is developed by using a combination of Pd and photoredox catalysts. This reaction proceeds under mild conditions and can be applied to a wide range of substrates including acyclic alkenyl triflates.

Macrolide Synthesis through Intramolecular Oxidative Cross-Coupling of Alkenes

A RhIII-catalyzed intramolecular oxidative cross-coupling between double bonds for the synthesis of macrolides is described. Under the optimized reaction conditions, macrocycles containing a diene moiety can be formed in reasonable yields and with excellent chemo- and stereoselectivity. This method provides an efficient approach to synthesize macrocyclic compounds containing a 1,3-conjugated diene structure.

Preparation of cyclopentyl (f) ene-1-boronic acid frequency that ester method

The invention discloses a method of preparing cyclopenten/cyclohexen-1-yl-boronic acid pinacol ester from methyl 1-cyclopentene/cyclohexene-1-carboxylate by three-step continuous operations. The method includes subjecting the raw material to alkaline hydrolysis to form the corresponding 1-alkylene carboxylic acid; performing addition with bromine; performing elimination and decarboxylation at the same time under the existence of DBU or DMAP to produce 1-bromo cyclopentene/cyclohexene; and allowing the 1-bromo cyclopentene/cyclohexene and methoxyboronic acid pinacol ester to form an ester under the existence of magnesium metal by a one-pot process to obtain the cyclopenten/cyclohexen-1-yl-boronic acid pinacol ester. The method is high in continuity, simple and convenient in operations, free of low-temperature reactions, and capable of obtaining the 1-bromo cyclopentene/cyclohexene intermediate with high purity and meeting market demands. The method adopts one-pot-process of Grignard reaction/esterification, so that the method is more convenient in operations and has less by-products, and the product is easier in rectification purification.

Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids

A series of α,β-unsaturated and α-bromo carboxylic acids were identified as potent antimicrobial agents. The antimicrobial activity was evaluated using the broth microdilution method. All acids 1-12 exhibited a significant activity against nine laboratory control strains of bacteria and two strains of yeast Candida albicans. The tested acids were efficiently prepared by optimized phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent with triethylbenzyl ammonium chloride (TEBA) as catalyst.

One-step conversion of ketones to conjugated acids using bromoform

Phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent result in the formation of ,-unsaturated carboxylic acids. The reaction was performed at room temperature for 24h. The corresponding conj

Synthesis of α,β-unsaturated carboxylic acids by nickel(II)-catalyzed electrochemical carboxylation of vinyl bromides

Electrochemical carboxylation of alkyl-substituted vinyl bromides (1a-1g) in the presence of 20 mol% of NiBr2?bpy under an atmospheric pressure of carbon dioxide with a platinum cathode and a magnesium anode gave the corresponding α,β-unsaturated carboxylic acids (2a-2g) in yields of 53-82%.

Structure-activity relationships of unsaturated analogues of valproic acid

The principal metabolite of valproic acid (VPA), 2-ene VPA, appears to share most of VPA's pharmacological and therapeutic properties while lacking its hepatotoxicity and teratogenicity, thus making it a useful lead compound for the development of safer antiepileptic drugs. Analogues of 2-ene VPA were evaluated for anticonvulsant activity in mice using the subcutaneous pentylenetetrazole test. Cyclooctylideneacetic acid exhibited a potency markedly exceeding that of VPA itself with only modest levels of sedation. Potency, as either ED50 or brain concentration, was highly correlated (r > 0.85) with volume and lipophilicity rather than with one of the shape parameters calculated by molecular modeling techniques, arguing against the existence of a specific receptor site. Instead, a role for the plasma membrane in mediating the anticonvulsant effect is suggested.

Dienediolates of Unsaturated Carboxylic Acids in Synthesis. Synthesis of Cyclohexenones and Polycyclic Ketones by Tandem Michael-Dieckmann Decarboxylative Annulation of Unsaturated Carboxylic Acids.

Substituted 2-cyclohexenones 4 to 7 and hexahydronaphthalenones and hexahydroindenones 13 to 18 are prepared by tandem Michael-Dieckmann addition of lithium dienediolates of acyclic and alicyclic unsaturated carboxylic acids to the lithium salts of the same or other unsaturated carboxylic acids.