(3aR,4R,5R,6aS)-5-(Benzoyloxy)-4-[(1E)-3,3-difluoro-4-phenoxy-1-butenyl]hexahydro-2H-cyclopenta[b]furan-2-one
[CAS# 209861-00-7]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: (3aR,4R,5R,6aS)-5-(Benzoyloxy)-4-[(1E)-3,3-difluoro-4-phenoxy-1-butenyl]hexahydro-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₂₄H₂₂F₂O₅
• Molecular Weight: 428.43
• CAS Registry Number: 209861-00-7
• SMILES: C1[C@H]2[C@H](CC(=O)O2)[C@H]([C@@H]1OC(=O)C3=CC=CC=C3)/C=C/C(COC4=CC=CC=C4)(F)F

Properties

• Solubility: Insoluble (1.7E^-3 g/L) (25 °C), Calc.^*
• Density: 1.31±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H319
• Safety Statements: P280-P305+P351+P351

Discovery and Applications

The chemical compound (3aR,4R,5R,6aS)-5-(Benzoyloxy)-4-[(1E)-3,3-difluoro-4-phenoxy-1-butenyl]hexahydro-2H-cyclopenta[b]furan-2-one represents a structurally complex molecule that has captured interest in organic synthesis and pharmaceutical research. This compound is part of a broader class of lactone derivatives, often associated with biologically active compounds, particularly those used in medicinal chemistry for drug development.

The discovery of this specific compound stems from efforts to modify cyclopentanoid structures with functional groups that enhance biological activity. Researchers have focused on adding difluoroalkyl and phenoxy substituents to lactones, as these modifications are known to improve the compound’s bioavailability, metabolic stability, and receptor binding affinity. The inclusion of the benzoyloxy and difluoro-phenoxy moieties in this compound provides both steric and electronic characteristics that make it valuable for probing receptor interactions in biological systems.

Applications of this compound, or structurally similar analogs, are primarily in the realm of drug design, particularly in the development of anti-inflammatory, antiviral, or anticancer agents. Its structural features enable selective interaction with biological targets such as enzymes or receptors involved in key metabolic pathways. In preclinical studies, similar compounds have been used as scaffolds to develop drugs with enhanced therapeutic properties, including increased potency and reduced side effects.

The combination of a difluoro-substituted alkenyl group and a phenoxy moiety offers specific advantages, such as improved lipophilicity, which allows for better membrane penetration. Additionally, these structural elements can stabilize the compound against metabolic degradation, making it a promising candidate for further drug optimization. The cyclopentanoid framework, present in many naturally occurring bioactive molecules, contributes to the molecule’s overall stability and potential biological activity.

In synthetic chemistry, this compound serves as an intermediate in multistep organic synthesis. Its stereochemistry and functional groups offer versatility for further chemical transformations, making it an important molecule for developing complex, bioactive compounds. The application of this compound in organic synthesis highlights its potential to serve as a building block for more intricate molecular architectures with therapeutic potential.

References

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