(2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol
[CAS# 133775-25-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol
• Molecular Formula: C₁₂H₁₃F₂N₃O₂
• Molecular Weight: 269.25
• CAS Registry Number: 133775-25-4
• EC Number: 818-289-4
• SMILES: C[C@H]([C@](CN1C=NC=N1)(C2=C(C=C(C=C2)F)F)O)O

Properties

• Solubility: Very slightly soluble (0.32 g/L) (25 °C), Calc.^*
• Density: 1.38±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H335
• Safety Statements: P261-P271-P304+P340-P319-P403+P233-P405-P501

Discovery and Applications

(2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol is an intriguing chemical compound with notable applications in medicinal chemistry and drug development. This molecule features a chiral butanediol backbone, with a difluorophenyl group and a 1,2,4-triazole moiety attached to it. The specific (2R,3R) stereochemistry of the butanediol component is crucial in determining the compound's biological activity and interactions.

The discovery of (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol was part of ongoing research aimed at identifying new compounds with potential therapeutic properties. The 2,4-difluorophenyl group is particularly notable for its ability to influence the compound's electronic properties and interaction with biological targets. Fluorine atoms enhance the molecule's stability and lipophilicity, which can improve its bioavailability and binding affinity.

The 1H-1,2,4-triazole ring is a versatile and important pharmacophore in medicinal chemistry. This heterocyclic structure is known for its ability to form hydrogen bonds and interact with various biological receptors and enzymes. The incorporation of the triazole moiety into the compound provides additional opportunities for designing selective and potent drugs.

The (2R,3R)-2,3-butanediol backbone introduces chirality into the molecule, which is a critical factor in drug design. The (2R,3R) configuration ensures specific spatial arrangement of the substituents, affecting the compound's interactions with biological targets and its overall efficacy. The presence of two hydroxyl groups in the butanediol structure allows for further chemical modifications and increases the molecule's versatility in synthesis.

One of the primary applications of (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol is in the development of novel pharmaceuticals. The compound's ability to interact with specific biological targets, combined with its fluorinated phenyl group, makes it a valuable candidate for drug discovery. It can be used as a lead compound or scaffold for designing new drugs with improved pharmacological properties.

The compound is also relevant in the field of agricultural chemistry. Its structure and functional groups can be leveraged to develop new agrochemicals or crop protection agents. The ability of the triazole moiety to interact with various biological systems makes it useful for creating chemicals that can target pests or diseases affecting crops.

The synthesis of (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol involves several key steps, including the introduction of the difluorophenyl and triazole groups onto the butanediol backbone. The stereochemistry of the butanediol moiety is controlled to ensure the (2R,3R) configuration, which is essential for the desired biological activity. Typically, the synthesis involves reactions such as nucleophilic substitutions, coupling reactions, and resolution steps to obtain the chiral compound with high purity.

In summary, (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol is a valuable compound in both medicinal and agricultural chemistry. Its unique structure and functional groups offer opportunities for developing new drugs and agrochemicals with specific properties. Continued research and development in this area are likely to uncover additional applications and benefits of this compound.

References

2014. Synthesis of Efinaconazole. Synfacts, 10(7).
DOI: 10.1055/s-0034-1378235

2009. Synthesis of Ravuconazole. Synfacts, 6(2).
DOI: 10.1055/s-0029-1218398