2607-03-6

Usage

Uses

Used in Perfumery and Personal Care Industry:
CIS-1,2-CYCLOBUTANEDICARBOXYLIC ACID DIMETHYL ESTER is utilized as a fragrance component in perfumes, enhancing their scent profiles and providing a pleasant, fruity aroma to the final product.
Used in Soap Production:
In the soap industry, CIS-1,2-CYCLOBUTANEDICARBOXYLIC ACID DIMETHYL ESTER serves as a flavoring agent, imparting a desirable scent to soaps and contributing to the overall sensory experience of the product.
Used in Organic Synthesis as a Solvent:
CIS-1,2-CYCLOBUTANEDICARBOXYLIC ACID DIMETHYL ESTER is employed as a solvent in organic synthesis processes, facilitating chemical reactions and aiding in the production of various compounds.
Used in Polymer Production as a Plasticizer:
In the polymer industry, this chemical compound functions as a plasticizer, improving the flexibility and workability of polymers, thus enhancing their utility in diverse applications.
It is crucial to handle CIS-1,2-CYCLOBUTANEDICARBOXYLIC ACID DIMETHYL ESTER with care due to its potential hazards. Inhalation or ingestion may be harmful, and it can cause skin and eye irritation, necessitating proper safety measures during its use.

InChI:InChI=1/C8H12O4/c1-11-7(9)5-3-4-6(5)8(10)12-2/h5-6H,3-4H2,1-2H3/t5-,6-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 4462-96-8 cis-1,2-cyclobutane dicarboxylic anhydride 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 4462-96-8 3-oxabicyclo[3.2.0]heptane-2,4-dione 

Downstream Products

• 35630-06-9 trans-1,2-cyclobutanedimethanol, bis(toluenesulfonate) 
• 7371-64-4 trans-(cyclobutane-1,2-diyl)dimethanol 
• 809-43-8 (1S,2S)-α,α,α',α'-tetraphenylcyclobutane-1,2-dimethanol 
• 221158-91-4 methyl 2-benzyloxycarbonylamino-(1R,2S)-cyclobutane-1-carboxylate 
• 517913-98-3 methyl (1S,2R)-2-(((benzyloxy)carbonyl)amino)cyclobutane-1-carboxylate 
• 221158-94-7 methyl 2-amino-(1R,2S)-cyclobutane-1-carboxylate 
• 874799-59-4 (1R,2S)-2-[2-Cyano-2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-cyclobutanecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of the constrained glutamate analogues (2S,1′R,2′R)- and (2S,1′S,2′S)-2-(2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I by enzymatic transamination

Optically pure trans-cyclobutane analogues of glutamic acid are prepared by highly selective enzymatic transamination of a single racemic trans-cyclobutane α-ketoglutaric acid derivative 5, which is synthesized in five steps from maleic anhydride. (2S,1′R,2′R)- and (2S,1′S,2′S)-2- (2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I are obtained using aspartate aminotransferase (AAT) and branched chain aminotransferase (BCAT), respectively.

Enantioselective synthetic approaches to cyclopropane and cyclobutane β-amino acids: Synthesis and structural study of a conformationally constrained β-dipeptide

Synthetic approaches to carbocyclic compounds, namely cyclopropane and cyclobutane β-amino acids, are presented. One of them is based on enzymatic desymmetrization of meso diesters, leading to the enantioselective production of cis-hemiesters, which afforded β-amino acids through Curtius rearrangements. The enantiomeric excess for the cyclobutane derivatives was 91% whereas the cyclopropanes were obtained in 63% ee. According to another strategy, an enantiomerically pure cyclopropane trans-β-amino acid, bearing a quaternary center, has been synthesized from a homochiral precursor easily available from D-glyceraldehyde. The preparation and structural investigation of the first synthesized cyclobutane containing dipeptide is also described. A hairpin-like conformation of this molecule in the solid state has been demonstrated by X-ray structural analysis, showing crystal packing induced by the presence of the rigid cyclobutane moiety and the formation of intermolecular hydrogen bonds. NMR experiments confirmed that these molecules also tend to produce aggregates in solution. On the contrary, theoretical calculations suggest that intramolecular interactions are important in the gas phase, as expected. Copyright (C) 2000 Elsevier Science Ltd.

Stereoselective synthesis of (-)-(1R,2S)-2-aminocyclobutane-1-carboxylic acid, a conformationally constrained β-amino acid

The title compound as well as some derivatives have been synthesized for the first time in optically active form by means of a chemoenzymatic transformation used to induce asymmetry in achiral precursors. The enantio- and diastereomeric purity has been determined by HPLC and NMR techniques.

A Study of Stereoselective Hydrolysis of Symmetrical Diesters with Pig Liver Esterase

Pig liver esterase (PLE) catalyzed hydrolysis of dimethyl esters of symmetrical dicarboxylic acids, including meso-diacids, cis-1,2-cycloalkanedicarboxylic acids, and diacids with a prochiral center, was studied with 14 substrates.The products of these stereoselective hydrolyses are chiral monoesters of dicarboxylic acids, with an enantiomeric excess (e.e.) from 10percent to 100percent.Some of these optically active monoesters are valuable synthons in natural products synthesis.An additivity pattern of α- and β-substituents with the glutaric esters on the stereoselectivity of enzymatic hydrolysis was observed.Analysis of the experimental results leads to a model of enzyme stereoselectivity of diester hydrolysis in which the substitution pattern at α- and β-C-atoms is found to determine the absolute configuration of the resulting monoester.