(3aR,4R,5R,6aS)-4-[(1E)-3,3-Difluoro-4-phenoxy-1-butenyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one
[CAS# 209861-01-8]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: (3aR,4R,5R,6aS)-4-[(1E)-3,3-Difluoro-4-phenoxy-1-butenyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₁₇H₁₈F₂O₄
• Molecular Weight: 324.32
• CAS Registry Number: 209861-01-8
• SMILES: C1[C@H]([C@@H]([C@@H]2[C@H]1OC(=O)C2)/C=C/C(COC3=CC=CC=C3)(F)F)O

Properties

• Solubility: Very slightly soluble (0.18 g/L) (25 °C), Calc.^*
• Density: 1.355±0.06 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)-4-[(1E)-3,3-Difluoro-4-phenoxy-1-butenyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one is an intriguing molecule belonging to a class of functionalized lactones. This compound features a difluoro-phenoxy substituted alkenyl chain and a hydroxyl group on a cyclopentanoid lactone framework, giving it both steric complexity and potential biological activity. The structure is notable for its stereochemistry and functional groups, making it useful in synthetic organic chemistry and drug discovery.

The discovery of this compound was driven by ongoing research into lactone derivatives and their biological activities. Lactones, particularly those with cyclopentanoid structures, have been recognized for their significant role in medicinal chemistry due to their involvement in natural product synthesis and biological signaling pathways. By incorporating difluoroalkyl and phenoxy functional groups into the structure, scientists aim to improve the pharmacokinetic properties of the molecule, such as its metabolic stability and membrane permeability. These modifications also enable the compound to interact more effectively with biological targets, such as enzymes and receptors.

Applications of (3aR,4R,5R,6aS)-4-[(1E)-3,3-Difluoro-4-phenoxy-1-butenyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one are primarily focused on the pharmaceutical field. Compounds of this nature have been studied as scaffolds for developing therapeutic agents, particularly in the areas of anti-inflammatory, anticancer, and antiviral drug development. The presence of the difluoro substituents on the alkenyl chain contributes to enhanced biological activity, as these groups can improve the compound's binding affinity to molecular targets and its resistance to metabolic degradation.

Moreover, the hydroxy-functionalized lactone core is important for increasing water solubility and facilitating interactions with biological receptors, making the compound a promising candidate for further drug design. Lactone-based structures are well-documented in medicinal chemistry for their bioactive properties, and this particular compound provides an excellent example of how chemical modification of a basic lactone framework can lead to compounds with improved therapeutic potential.

In synthetic chemistry, the stereochemistry and functional groups of this compound allow for its use as an intermediate in the development of more complex molecules. Its difluoro and phenoxy groups are especially valuable for constructing molecules that require precise electronic and steric configurations, such as those used in pharmaceutical synthesis.

References

2020. Synthesis of Tafluprost. Synfacts.
DOI: 10.1055/s-0040-1707020

2010. Tafluprost. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-20-0221