773100-29-1 | 1-(4-FLUORO-PHENYL)-CYCLOPROPANECARBOXYLIC ACID

CAS:773100-29-1 | 1-(4-FLUORO-PHENYL)-CYCLOPROPANECARBOXYLIC ACID,Description

1-(4-Fluorophenyl)cyclopropanecarboxylic acid is a compound that features a cyclopropane ring with a carboxylic acid functional group and a 4-fluorophenyl substituent. This structure is of interest due to the unique properties imparted by the strained cyclopropane ring and the electron-withdrawing fluorine atom, which can influence the reactivity and physical properties of the molecule.

Synthesis Analysis

The synthesis of related fluorinated cyclopropanecarboxylic acids has been explored in various studies. For instance, a rhodium-catalyzed cyclopropanation method has been used for the stereoselective synthesis of cis-2-fluorocyclopropanecarboxylic acid, demonstrating the utility of transition metal catalysis in constructing such compounds. Additionally, multi-step synthetic routes involving nucleophilic substitution reactions and ester hydrolysis have been employed to synthesize N-(4-fluorophenyl)-1-(pyrrolidine-1-carbonyl) cyclopropane-1-carboxamide, indicating the versatility of cyclopropane derivatives in organic synthesis.

Molecular Structure Analysis

The molecular structure of cyclopropane derivatives has been extensively studied. For example, the structure and absolute configuration of (R)-(+)-1-fluoro-2,2-diphenylcyclopropanecarboxylic acid were determined using single-crystal X-ray diffraction methods, revealing the orthogonal orientation of the carboxylic group to the cyclopropane ring and the dihedral angles between the phenyl rings and the cyclopropane ring. These structural insights are crucial for understanding the reactivity and interaction of the molecule with other chemical entities.

Chemical Reactions Analysis

Fluorinated cyclopropane carboxylic acids can participate in various chemical reactions due to their strained ring system and the presence of reactive functional groups. The synthesis of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid derivatives, which have antibacterial properties, showcases the reactivity of such compounds in the formation of complex heterocyclic structures. Moreover, the antimycobacterial evaluation of newer 1-cyclopropyl-1,4-dihydro-6-fluoro-7-(substituted secondary amino)-8-methoxy-5-(sub)-4-oxoquinoline-3-carboxylic acids highlights the potential of these molecules in medicinal chemistry.

Physical and Chemical Properties Analysis

The physical and chemical properties of fluorinated cyclopropane carboxylic acids are influenced by the presence of the fluorine atom and the cyclopropane ring. A microwave and quantum chemical study of 1-fluorocyclopropanecarboxylic acid provided insights into the conformational properties and intramolecular hydrogen bonding of the molecule, which are important for understanding its behavior in different environments. The inclusion compounds of cis- and trans-3,3-bis(4-methylphenyl)cyclopropane-1,2-dicarboxylic acid hosts with ethanol guests further illustrate the complex intermolecular interactions that can occur with such molecules.

Scientific Research Applications

Application 1: Intermediate for Cabozantinib Synthesis 

• Summary of the Application : “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” is used as a key intermediate in the synthesis of Cabozantinib. Cabozantinib is a drug used to treat various types of cancer.
• Results or Outcomes : The successful synthesis of Cabozantinib using “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” as an intermediate allows for the production of a potent anti-cancer drug. The effectiveness of Cabozantinib in treating cancer has been demonstrated in numerous clinical trials.

Application 2: Intermediate for 1-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid Synthesis

• Summary of the Application : “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” can be used as an intermediate in the synthesis of "1-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid". This compound could have potential applications in various fields of research.
• Methods of Application or Experimental Procedures : The specific procedures for using “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” in the synthesis of “1-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid” are proprietary and may vary between laboratories.
• Results or Outcomes : The successful synthesis of “1-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid” using “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” as an intermediate could open up new avenues for research.

Application 3: Research Chemical

• Summary of the Application : “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” is a useful research chemical that can be used in various chemical reactions.
• Methods of Application or Experimental Procedures : The specific procedures for using “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” in chemical reactions are proprietary and may vary between laboratories.
• Results or Outcomes : The use of “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” in chemical reactions could lead to the discovery of new compounds and reactions.

Application 4: Intermediate for 1-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid Synthesis

• Summary of the Application : “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” can be used as an intermediate in the synthesis of "1-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid". This compound could have potential applications in various fields of research.
• Methods of Application or Experimental Procedures : The specific procedures for using “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” in the synthesis of “1-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid” are proprietary and may vary between laboratories.
• Results or Outcomes : The successful synthesis of “1-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid” using “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” as an intermediate could open up new avenues for research.

Application 5: Research Chemical

• Summary of the Application : “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” is a useful research chemical that can be used in various chemical reactions.
• Methods of Application or Experimental Procedures : The specific procedures for using “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” in chemical reactions are proprietary and may vary between laboratories.
• Results or Outcomes : The use of “1-(4-Fluorophenyl)cyclopropanecarboxylic acid” in chemical reactions could lead to the discovery of new compounds and reactions.

Safety And Hazards

The compound is classified as an eye damager (Eye Dam. 1) according to the Globally Harmonized System of Classification and Labelling of Chemicals (GHS). The safety information suggests that precautions should be taken to avoid eye contact.

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