• 1. A convenient approach to β-heteroarylated (C–N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles
  M. Bhanuchandra,Malleswara Rao Kuram,Akhila K. Sahoo Org. Biomol. Chem. 2012 10 3538

Introduction to 3-(3-fluorophenyl)prop-2-yn-1-ol (CAS No. 197239-54-6)

3-(3-fluorophenyl)prop-2-yn-1-ol, identified by its Chemical Abstracts Service number CAS No. 197239-54-6, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound, featuring a propargyl alcohol moiety attached to a 3-fluorophenyl group, exhibits unique structural and functional properties that make it a promising candidate for various biochemical applications.

The molecular structure of 3-(3-fluorophenyl)prop-2-yn-1-ol consists of a propargyl group (C?H?N) linked to a benzene ring substituted with a fluorine atom at the 3-position. This fluorine substitution enhances the electronic properties of the aromatic ring, influencing its reactivity and interaction with biological targets. The presence of the propargyl alcohol functionality provides a versatile handle for further chemical modifications, enabling the synthesis of more complex derivatives with tailored pharmacological profiles.

In recent years, the demand for fluorinated aromatic compounds has surged due to their enhanced metabolic stability and improved binding affinity to biological receptors. 3-(3-fluorophenyl)prop-2-yn-1-ol is no exception, as it has been explored in several cutting-edge research projects aimed at developing novel therapeutic agents. Its unique combination of structural features positions it as a valuable intermediate in the synthesis of small-molecule drugs targeting neurological disorders, inflammatory conditions, and infectious diseases.

One of the most compelling aspects of 3-(3-fluorophenyl)prop-2-yn-1-ol is its potential in drug discovery and development. The fluorine atom at the 3-position of the phenyl ring modulates the electronic distribution, which can significantly influence the compound's interaction with enzymes and receptors. This modulation is particularly crucial in designing drugs that require high selectivity and potency. Recent studies have demonstrated that fluorinated propargyl alcohols exhibit promising activity against enzymes involved in cancer metabolism, making them attractive candidates for further investigation.

Moreover, the propargyl alcohol group in 3-(3-fluorophenyl)prop-2-yn-1-ol serves as an excellent site for further functionalization through cross-coupling reactions such as Suzuki-Miyaura or Sonogashira couplings. These reactions allow for the introduction of diverse substituents, enabling the creation of libraries of derivatives with varying pharmacological properties. Such chemical flexibility is invaluable in high-throughput screening programs aimed at identifying lead compounds for drug development.

The compound's relevance extends to its role in synthetic chemistry, where it serves as a building block for more complex molecules. The combination of a fluorinated aromatic ring and a propargyl alcohol provides a scaffold that can be modified to target specific biological pathways. For instance, researchers have explored its utility in synthesizing inhibitors of kinases and other enzymes implicated in signal transduction pathways associated with chronic diseases.

Recent advancements in computational chemistry have further highlighted the potential of 3-(3-fluorophenyl)prop-2-yn-1-ol as a pharmacophore. Molecular modeling studies suggest that this compound can effectively interact with binding pockets of target proteins, offering insights into its mechanism of action. These computational approaches complement experimental efforts by predicting binding affinities and identifying optimal conformations for drug-like activity.

In addition to its pharmaceutical applications, 3-(3-fluorophenyl)prop-2-yn-1-ol has shown promise in materials science, particularly in the development of advanced polymers and liquid crystals. The fluorine atom's electron-withdrawing effect can influence polymer properties such as thermal stability and solubility, making this compound a valuable asset in designing high-performance materials.

The synthesis of 3-(3-fluorophenyl)prop-2-yn-1-ol typically involves multi-step organic transformations starting from commercially available precursors. Key steps include halogenation of the phenyl ring followed by protection-deprotection strategies to install the propargyl alcohol functionality. Advances in synthetic methodologies have improved both yield and purity, making large-scale production more feasible for research and industrial applications.

Evaluation of 3-(3-fluorophenyl)prop-2-yn-1-ol in preclinical studies has revealed several interesting findings. Its interaction with biological targets suggests potential therapeutic benefits, particularly in modulating inflammatory responses and inhibiting pathogenic enzymes. While further research is needed to fully elucidate its pharmacological profile, these preliminary results underscore its significance as a chemical entity with broad applicability.

The future direction of research on 3-(3-fluorophenyl)prop-2-ylnol (CAS No. 19723954) likely involves expanding its chemical space through innovative synthetic strategies and exploring novel biological targets. Collaborative efforts between synthetic chemists and biologists will be essential in unlocking its full potential as a therapeutic agent or material component.

• 778549-42-1(Hydroxylamine,O-[3-(3-fluorophenyl)-2-propyn-1-yl]-)
• 61794-52-3(2-Propyn-1-ol, 3,3'-(2,3,5,6-tetrafluoro-1,4-phenylene)bis-)
• 61794-51-2(2-Propyn-1-ol, 3-(2,3,5,6-tetrafluorophenyl)-)
• 61794-48-7(2-Propyn-1-ol, 3-(2,3,5,6-tetrafluoro-4-methylphenyl)-)
• 61794-45-4(2-Propyn-1-ol, 3-(pentafluorophenyl)-)
• 229015-32-1(3-Butyn-2-ol,4-(4-fluorophenyl)-)
• 229015-35-4(3-Butyn-2-ol,4-(4-fluorophenyl)-, (2S)-)
• 273938-11-7(Benzene,1-fluoro-3-(3-methoxy-1-propyn-1-yl)-)
• 220708-01-0(2-Propyn-1-ol,3-(4-fluoro-3-methylphenyl)-)
• 80151-28-6(3-(4-Fluoro-Phenyl)-Prop-2-Yn-1-Ol)