Cas no 1213923-45-5 ((2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol)

(2R)-2-Amino-2-(5-fluoropyridin-3-yl)ethan-1-ol is a chiral amino alcohol derivative featuring a fluoropyridine moiety, which imparts unique reactivity and selectivity in synthetic applications. The (R)-configuration ensures enantioselectivity, making it valuable for asymmetric synthesis and pharmaceutical intermediates. The fluorine substituent enhances metabolic stability and binding affinity in bioactive compounds, while the pyridine ring offers coordination potential for metal-catalyzed reactions. Its bifunctional structure—combining an amino group and a hydroxyl group—facilitits use in peptidomimetics and ligand design. This compound is particularly useful in medicinal chemistry for the development of fluorinated analogs with improved pharmacokinetic properties. High purity and well-defined stereochemistry ensure reproducibility in research and industrial applications.
(2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol structure
1213923-45-5 structure
Product Name:(2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol
CAS No:1213923-45-5
MF:C7H9FN2O
MW:156.157564878464
CID:2184448
PubChem ID:124222634
Update Time:2025-06-29

(2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol Chemical and Physical Properties

Names and Identifiers

    • (2R)-2-amino-2-(5-fluoro(3-pyridyl))ethan-1-ol
    • (2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol
    • (2R)-2-Amino-2-(5-fluoropyridin-3-yl)ethanol
    • Inchi: 1S/C7H9FN2O/c8-6-1-5(2-10-3-6)7(9)4-11/h1-3,7,11H,4,9H2/t7-/m0/s1
    • InChI Key: JTFJNWJSUFENLY-ZETCQYMHSA-N
    • SMILES: FC1=CN=CC(=C1)[C@H](CO)N

Computed Properties

  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 123
  • Topological Polar Surface Area: 59.1

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(2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol Related Literature

Additional information on (2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol

Introduction to (2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol (CAS No. 1213923-45-5)

(2R-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol) is a significant compound in the field of pharmaceutical chemistry, characterized by its unique structural and functional properties. This compound, identified by its CAS number CAS No. 1213923-45-5, has garnered attention due to its potential applications in the development of novel therapeutic agents. The presence of a fluorine substituent and a pyridine ring in its molecular structure imparts distinct chemical and biological characteristics, making it a valuable scaffold for drug discovery.

The compound's stereochemistry, specifically the (2R) configuration, plays a crucial role in determining its biological activity. Chiral centers are often pivotal in pharmaceuticals, as they can significantly influence the efficacy and selectivity of a drug. The research on stereospecific compounds like (2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol has been a focal point in medicinal chemistry, aiming to optimize drug design for better pharmacokinetic profiles.

In recent years, there has been a surge in interest regarding fluorinated pyridines in drug development. These motifs are known for their ability to enhance metabolic stability, improve binding affinity, and modulate pharmacological properties. The incorporation of a fluorine atom at the 5-position of the pyridine ring in (2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol contributes to its unique chemical behavior, making it an attractive candidate for further investigation.

The compound's potential applications extend to various therapeutic areas. For instance, fluorinated pyridines have been explored in the development of antiviral and anticancer agents due to their ability to interact with biological targets in a specific manner. The amine group in (2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol provides a versatile site for further functionalization, allowing chemists to design derivatives with enhanced biological activity.

Recent studies have highlighted the importance of fluorinated pyridines in modulating enzyme inhibition. For example, compounds containing this moiety have shown promise in inhibiting kinases and other enzymes involved in cancer pathways. The stereochemistry of (2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol may play a critical role in determining its selectivity for these targets, thereby minimizing off-target effects.

The synthesis of (2R)-2-amino-2-(5-fluoropyridin-3-yl)ethan-1-ol presents unique challenges due to its complex structure. Advanced synthetic methodologies, such as asymmetric hydrogenation and cross-coupling reactions, are often employed to achieve the desired stereochemical purity. These techniques require meticulous optimization to ensure high yields and enantiomeric excess, which are crucial for pharmaceutical applications.

In conclusion, (2R)-2-amino-2-(5-fluoropyridin-3-ylenthananol) represents a promising compound with significant potential in drug discovery. Its unique structural features, including the (2R) stereochemistry and the presence of a fluorinated pyridine moiety, make it an attractive scaffold for developing novel therapeutic agents. Further research is warranted to explore its full pharmacological profile and to optimize its synthesis for industrial-scale production.

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