92828-74-5

Usage

Monomeric Building Block

Used as a starting material in the production of polymeric materials.

Physical State

Colorless, viscous liquid
Describes the appearance and consistency of the compound.

High Boiling Point

Indicates that the compound has a high resistance to evaporation, making it suitable for various industrial applications.

Chemical Structure

Cyclobutane ring with dicarboxylic acid and phenylmethyl ester groups
Describes the core structure of the compound, including the arrangement of atoms and functional groups.

cis-Configuration

Refers to the arrangement of the substituent groups around the cyclobutane ring, which affects the compound's properties and reactivity.

Phenylmethyl Ester Group

The presence of this group imparts desirable properties to the compound, such as high thermal stability and resistance to degradation.

Industrial Applications

The compound is valuable in the development of advanced materials for various industries, such as plastics, coatings, and adhesives.

Polymer Synthesis

Used as a key component in the synthesis of polymers with specific properties, such as strength, flexibility, and durability.

Chemical Stability

The compound is stable under normal conditions, making it suitable for use in various chemical processes and applications.

Upstream product

• 4462-96-8 cis-1,2-cyclobutane dicarboxylic anhydride 
• 100-51-6 benzyl alcohol 

Downstream Products

• 82588-24-7 benzyl (+/-)-cis-2-acetoxycyclobutanecarboxylate 
• 82588-22-5 benzyl (+/-)-cis-2-acetylcyclobutanecarboxylate 
• 82588-20-3 (+/-)-cis-carbobenzoxycyclobutanecarbonyl chloride 

Relevant academic research and scientific papers

(+/-)-cis-2-Acetoxycyclobutyltrimethylammonium Iodide: A Semirigid Analogue of Acetylcholine

The title compound was prepared to complete a series of small ring (cyclopropane, cyclobutane) cis/trans 1,2-disubstituted semirigid congeners of acetylcholine.A multistep synthetic sequence, beginning with cis-cyclobutane-1,2-dicarboxylic anhydride, permitted unequivocal preparation of the (+/-)-cis target compound 4.The geometry of 4 was confirmed by comparison with an authentic sample of the (+/-)-trans isomer.The cis and trans isomers were equipotent as muscarinic agonists, but they were much weaker than acetyl-β-methylcholine.

Stereoselective chemoenzymatic synthesis of the four stereoisomers of L-2-(2-carboxycyclobutyl)glycine and pharmacological characterization at human excitatory amino acid transporter subtypes 1, 2, and 3

The four stereoisomers of L-2-(2-carboxycyclobutyl)glycine, L-CBG-I, L-CBG-II, L-CBG-III, and L-CBG-IV, were synthesized in good yield and high enantiomeric excess, from the corresponding cis and trans-2- oxalylcyclobutanecarboxylic acids 5 and 6 using the enzymes aspartate aminotransferase (AAT) and branched chain aminotransferase (BCAT) from Escherichia coli. The four stereoisomeric compounds were evaluated as potential ligands for the human excitatory amino acid transporters, subtypes 1, 2, and 3 (EAAT1, EAAT2, and EAAT3) in the FLIPR membrane potential assay. While the one trans-stereoisomer, L-CBG-I, displayed weak substrate activity at all three transporters, EAAT1-3, we found a particular pharmacological profile for the other trans-stereoisomer, L-CBG-II, which displayed EAAT1 substrate activity and inhibitory activity at EAAT2 and EAAT3. Whereas L-CBG-III was found to be a weak inhibitor at all three EAAT subtypes, the other cis-stereoisomer L-CBG-IV was a moderately potent inhibitor with 20-30-fold preference for EAAT2/3 over EAAT1.