127199-13-7

Usage

Uses

Used in Organic Synthesis:
(1R,2R)-2-fluorocyclopropanecarboxylic acid serves as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for the creation of new molecules with distinct properties, making it a versatile component in the development of novel chemical entities.
Used in Drug Development:
In the pharmaceutical industry, (1R,2R)-2-fluorocyclopropanecarboxylic acid is utilized as a starting material for the design and synthesis of new drugs. Its incorporation into drug candidates can potentially enhance their biological activity, selectivity, and pharmacokinetic properties, leading to the discovery of innovative therapeutic agents.
Used in Medicinal Chemistry:
(1R,2R)-2-fluorocyclopropanecarboxylic acid is employed as a structural motif in medicinal chemistry to explore its potential as a pharmacophore. Its introduction into drug molecules can impart specific interactions with biological targets, contributing to the development of compounds with improved efficacy and selectivity.
Used in Agrochemicals:
(1R,2R)-2-fluorocyclopropanecarboxylic acid also finds application in the agrochemical sector, where it is used as a building block for the synthesis of novel pesticides and herbicides. Its unique structure and reactivity can lead to the development of more effective and environmentally friendly agrochemicals.

InChI:InChI=1S/C4H5FO2/c5-3-1-2(3)4(6)7/h2-3H,1H2,(H,6,7)/t2-,3+/m0/s1

Upstream product

• 137081-42-6 2-chloro-2-fluorocyclopropane carboxylic acid 
• 152237-14-4 tert-butyl 2-fluoro-cyclopropane-1-carboxylate 
• 188428-48-0 cis-ethyl 2-fluorocyclopropanecarboxylate 
• 216872-00-3 (1R,2R)-2-Fluoro-cyclopropanecarboxylic acid propyl ester 
• 161582-46-3 (1R,2R)-2-Fluoro-cyclopropanecarboxylic acid butyl ester 
• 127199-12-6 (1R,2R)-2-Fluoro-cyclopropanecarboxylic acid ((R)-1-phenyl-ethyl)-amide 

Downstream Products

• 127199-12-6 2-Fluoro-cyclopropanecarboxylic acid ((R)-1-phenyl-ethyl)-amide 
• 185225-82-5 cis-2-fluorocyclopropanoyl chloride 
• 169884-67-7 [(1R,2R)-2-fluorocyclopropyl]methanol 

Relevant academic research and scientific papers

Purification, properties and reactivity of the esterase from Micrococcus sp.

The esterase from Micrococcus sp., which hydrolyzes n-propyl-2- fluorocyclopropanecarboxylate (3) enantioselectively, was highly purified by three types of chromatography. The purified enzyme was inactivated by Hg and diisopropyl fluorophosphate (DFP). It was a monomer with a molecular weight of about 35000. The enzyme exhibits esterase activity towards many aliphatic propyl esters. The enantioselectivity for substrate (3) using purified enzyme did not differ from that of crude enzyme.

Stereoselective synthesis of cis -2-fluorocyclopropanecarboxylic acid

A rhodium-catalyzed cyclopropanation of 1-fluoro-1-(phenylsulfonyl)ethylene and diazo esters is described as an effective method for the stereoselective synthesis of cis-2-fluorocyclopropanecarboxylic acid. This process provides an example of the cyclopro

PROCESS FOR PRODUCING 1,2-CIS-2-FLUOROCYCLOPROPANE-1-CARBOXYLIC ESTER COMPOUND

Provided is an industrially applicable process for producing 1,2-cis-2-fluorocyclopropane-1-carboxylic ester. A process for producing a compound represented by formula (3): [wherein R 1 represents, for example, a C1-C8 alkyl group], which process includes reacting a compound represented by formula (1) : [wherein X 1 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom; X 2 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom; X 1 and X 2 are not simultaneously hydrogen atoms; and R 1 has the same meaning as defined in formula (3)] with a reducing agent represented by formula (2): €?€?€?€?€?€?€?€?M 1 BH m R 2 n (2-1) or M 2 (BH m R 2 n ) 2 €?€?€?€?€?(2-2) [wherein M 1 represents an alkali metal atom; M 2 represents an alkaline earth metal atom or a zinc atom; R 2 represents, for example, a hydrogen atom; m represents an integer from 1 to 4; n represents an integer from 0 to 3; and the sum of m and n is 4] in the presence of an aprotic polar solvent, and a Lewis acid such as a halide of an atom selected from among, for example, boron, magnesium, and aluminum.

Resolution of cis-2-fluorocyclopropanecarboxylic acid by a microbial enantioselective hydrolysis

The important key intermediate of quinolone analogue synthesis, (1S,2S)- 2-fluorocyclopropanecarboxylic acid, was prepared enantioselectively by a microbial resolution. One of the strains with the highest enzymatic specificity was selected from soil and when lyophilized cells were treated with corresponding ester, the remaining (1S,2S)-ester was obtained with high enantiomeric purity (98% e.e.).

(Fluorocyclopropyl)quinolones. 2. Synthesis and stereochemical structure- activity relationships of chiral 7-(7-amino-5-azaspiro[2.4]heptan-5-yl)-1- (2-fluorocyclopropyl)quinolone antibacterial agents

A series of novel chiral 7-(7-amino-5-azaspiro[2.4]heptan-5-yl)-8-chloro- 1-(2-fluorocyclopropyl)-quinolones were synthesized as a continuation of a research project of 1-(2-fluorocyclopropyl)-quinolones by considering stereochemical and physicochemical properties of the molecule. Absolute configurations of the 1-(cis-2-fluorocyclopropyl) moiety and the 7-(7-amino- 5-azaspiro-[2.4]heptan-5-yl) moiety were determined by X-ray crystallographic analysis. Stereochemical structure-activity relationship studies indicated that 1-[(1R,2S)-2-fluorocyclopropyl] and 7-[(7S)-amino-5-azaspiro[2.4]heptan- 5-yl] derivatives are more potent against Gram-positive and Gram-negative bacteria than the other stereoisomers and 7-[(7S)-7-amino-5-azaspiro[2.4]- heptan-5-yl]-8-chloro-1-[(1R,2S)-2-fluorocyclopropyl]quinolone (33) is the most potent of all stereoisomers. Pharmacokinetic profiles and physicochemical properties of the selected compounds were also examined, and it was found that 33 (DU-6859a) possesses moderate lipophilicity and good pharmacokinetic profiles.

Fluorinated cyclopropanecarboxylic acids and their derivatives

The addition of halofluorocarbenes such as :CF2, :CClF or :CBrF, generated from the appropriate halofluoromethanes with bases, to butadiene or isoprene gives the corresponding l-vinyl substituted halofluorocyclopropanes in moderate to good yield. The vinyl group facilitates the carbene addition and permits a subsequent wide derivatisation. Several transformations including hydroboration, oxidation and Curtius degradation are presented. Furthermore, replacement of the chlorine atom in 2-chloro-2-fluorocyclopropanecarboxylic acid derivatives by hydrogen is achieved catalytically with Raney nickel. This sequence provides a convenient route to mono-fluorine substituted cyclopropane carboxylic acids.