(1R,2R)-2-fluorocyclopropanecarboxylic acid

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Cat Number

INT127199137

CAS Number

127199-13-7

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Product Detail Description Customer Q&A

CAS Number

127199-13-7

Storage

2-8℃

Synonyms

(1R,2R)-2-Fluorocyclopropane-1-carboxylic acid

Molecular Formula

C4H5FO2

Molecular Weight

104.08

Smiles

C1[C@@H]([C@@H]1F)C(=O)O

Appearance

Off-white to light yellow solid

Boiling Point

202.3℃

Relative Density

1.35

pKa

3.78

General Description

(1R,2R)-2-fluorocyclopropanecarboxylic acid is a specialized chiral building block featuring a cyclopropane ring substituted with a fluorine atom and a carboxylic acid moiety. As a key intermediate in medicinal chemistry, this compound provides a rigid, fluorinated structural framework that is highly valued for the synthesis of complex pharmaceutical molecules. Its specific (1R, 2R) configuration is essential for maintaining the desired three-dimensional shape required for high-affinity biological interactions.

Mechanism of Action

(1R,2R)-2-fluorocyclopropanecarboxylic acid functions by introducing a fluorinated cyclopropyl group into a scaffold, which significantly alters the physicochemical and metabolic properties of the final compound. The rigid cyclopropane ring restricts the conformational flexibility of the molecule, while the electronegative fluorine atom enhances lipophilicity and increases metabolic stability. By serving as a starting material for amide or ester linkages, it enables the integration of this optimized motif into biologically active targets, such as bacterial topoisomerases or specialized receptor inhibitors.

Application

(1R,2R)-2-fluorocyclopropanecarboxylic acid is primarily utilized as a critical intermediate in the synthesis of advanced fluoroquinolone antibiotics, including Sitafloxacin. It is also used in academic and industrial research for the development of chiral libraries, asymmetric synthesis, and as a specialized reagent in studies exploring the impact of fluorine-substituted cyclopropanes on the structure-activity relationship (SAR) of novel drug candidates.

What is the structural significance of the (1R,2R) configuration in (1R,2R)-2-fluorocyclopropanecarboxylic acid?

The (1R,2R) configuration in it ensures the precise stereochemical orientation necessary for it to bind effectively to specific biological targets.

How does the fluorine atom in (1R,2R)-2-fluorocyclopropanecarboxylic acid influence its biological activity?

The fluorine atom in it increases lipophilicity and prevents oxidative degradation, leading to improved pharmacological profiles in the final drug.

What is the main pharmaceutical application for (1R,2R)-2-fluorocyclopropanecarboxylic acid?

It is primarily used as a key building block for the synthesis of advanced fluoroquinolone antibiotics like Sitafloxacin.

How should (1R,2R)-2-fluorocyclopropanecarboxylic acid be stored?

It should be stored in a cool, dry place in a tightly sealed container to prevent moisture absorption and maintain its chemical stability.