127199-14-8 | (1S,2S)-2-Fluorocyclopropanecarboxylic acid

CAS:127199-14-8 | (1S,2S)-2-Fluorocyclopropanecarboxylic acid,Description

“(1S,2S)-2-Fluorocyclopropanecarboxylic Acid” is a useful research chemical. It has a molecular weight of 104.08 and a molecular formula of C4H5FO2. The IUPAC name for this compound is (1S,2S)-2-fluorocyclopropane-1-carboxylic acid.

Synthesis Analysis

A novel method for asymmetric synthesis of (1S,2S)-2-fluorocyclopropanecarboxylic acid under catalysis of a chiral rhodium catalyst has been reported. The chiral rhodium catalyst can catalyze asymmetric ring closure reaction of 1-fluoro-1-phenylsulfonyl ethylene and ethyl diazoacetate.

Molecular Structure Analysis

The molecular structure of this compound can be represented by the canonical SMILES string: C1C(C1F)C(=O)O. The InChI string for this compound is InChI=1S/C4H5FO2/c5-3-1-2(3)4(6)7/h2-3H,1H2,(H,6,7)/t2-,3+/m1/s1.

Physical And Chemical Properties Analysis

This compound has a predicted density of 1.35±0.1 g/cm3. It is a white solidand is soluble (34 g/L) at 25 ºC. The predicted boiling point is 202.3±33.0 ºC. The pKa of this compound is predicted to be 3.78±0.20.

Scientific Research Applications

Enantioselective Synthesis

• Resolution of cis-2-fluorocyclopropanecarboxylic acid: Enantioselective synthesis of (1S,2S)-2-fluorocyclopropanecarboxylic acid, a key intermediate in quinolone analogue synthesis, was achieved through microbial resolution. A specific microbial strain, selected from soil, showcased high enzymatic specificity for the ester of the compound, resulting in high enantiomeric purity (98% e.e.) (Imura, Itoh, & Miyadera, 1998).

Pharmacological Applications

• Synthesis of mGluR2 antagonist: A compound, (+)-(1R( *),2R( *))-2-[(1S( *))-1-amino-1-carboxy-2-(9H-xanthen-9-yl)-ethyl]-1-fluorocyclopropanecarboxylic acid (+)-16a, was synthesized. It demonstrated affinity for mGluR2 and exhibited a superior pharmacokinetic profile compared to the parent compound (Sakagami et al., 2008).

Structural and Conformational Studies

• Microwave and quantum chemical study: The conformational properties and intramolecular hydrogen bonding of 1-fluorocyclopropanecarboxylic acid were explored using microwave spectroscopy and various quantum chemical calculations. This study provided insights into the stable conformers of the compound and their properties, including dipole moments and stability relative to each other (Møllendal, Leonov, & de Meijere, 2005) .

Synthesis and Study of Derivatives

• Stereoselective synthesis: A rhodium-catalyzed cyclopropanation method was used for the stereoselective synthesis of cis-2-fluorocyclopropanecarboxylic acid. This process exemplified the cyclopropanation of electron-deficient olefins and diazoacetates (Shibue & Fukuda, 2014).

Potential Therapeutic Applications

• Antibacterial activity: Novel 6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-4-oxoquinoline-3-carboxylic acids with cyclopropane-fused 2-amino-8-azabicyclo[4.3.0]nonan-8-yl substituents at the C-7 position were synthesized. Some compounds exhibited excellent antibacterial activity and potent inhibitory activity against bacterial DNA topoisomerase IV (Inagaki, Takahashi, & Takemura, 2004).

Safety And Hazards

This compound is classified as a danger according to the GHS hazard statement. It causes severe skin burns and eye damage. The precautionary statements include avoiding breathing dust/fume/gas/mist/vapors/spray, washing thoroughly after handling, using only outdoors or in a well-ventilated area, wearing protective gloves/protective clothing/eye protection/face protection, and others.

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