(3aR,4R,5R,6aS)-5-(Benzoyloxy)hexahydro-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-2-one
[CAS# 208111-98-2]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: (3aR,4R,5R,6aS)-5-(Benzoyloxy)hexahydro-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-2-one
• Synonyms: [(3aR,4R,5R,6aS)-2-oxo-4-[(E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] benzoate
• Molecular Formula: C₂₅H₂₁F₃O₆
• Molecular Weight: 474.43
• CAS Registry Number: 208111-98-2
• SMILES: C1[C@H]2[C@H](CC(=O)O2)[C@H]([C@@H]1OC(=O)C3=CC=CC=C3)/C=C/C(=O)COC4=CC=CC(=C4)C(F)(F)F

Properties

• Density: 1.38

Discovory and Applicatios

The compound (3aR,4R,5R,6aS)-5-(Benzoyloxy)hexahydro-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-2-one is a synthetic organic molecule belonging to the class of cyclopentafuran derivatives. The discovery of this compound can be linked to the growing interest in the development of highly functionalized cyclic structures for applications in medicinal chemistry and materials science. The combination of furan and cyclopentane moieties within the molecular framework, coupled with the presence of a trifluoromethyl group, indicates that this compound is designed to interact with biological systems or serve as a precursor in advanced materials.

The synthesis of this compound involves the cyclization of functionalized intermediates, typically utilizing strategies such as aldol condensation or Michael addition. The stereochemistry, represented by the (3aR,4R,5R,6aS) configuration, is crucial for its activity and application, as stereochemical arrangement can significantly affect molecular interactions with biological targets or catalytic environments. The introduction of a trifluoromethylphenoxy group suggests an interest in modifying the compound’s electronic properties, potentially enhancing its stability, bioavailability, or interaction with enzymes.

The application of (3aR,4R,5R,6aS)-5-(Benzoyloxy)hexahydro-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-2-one spans several areas. In medicinal chemistry, it can be explored for its potential as an inhibitor of key enzymes or as a scaffold for drug development. The trifluoromethyl group is known to increase metabolic stability and lipophilicity, which are valuable properties in drug design. This makes the compound a candidate for pharmacological studies aiming to discover new treatments for diseases where small, lipophilic molecules are effective.

Additionally, the presence of the benzoyloxy group and cyclopentafuran core suggests that the compound may be useful in materials science, particularly in the development of new polymers or coatings. Its rigid, yet functionalized structure could be applied in creating materials with specific electronic or mechanical properties.

In biological applications, the molecule’s trifluoromethylphenoxy group is of particular interest. Trifluoromethyl-containing compounds are widely studied for their ability to modulate the activity of proteins, enzymes, and other biomolecules. This could extend the compound’s application into biochemical research or as a probe for studying enzyme inhibition and receptor interactions.

Overall, (3aR,4R,5R,6aS)-5-(Benzoyloxy)hexahydro-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-2-one represents a complex, multifunctional compound with broad potential in medicinal chemistry and materials science. Its unique stereochemistry and functional groups allow for exploration in various scientific fields.