(1S,5R)-2-Oxabicyclo[3.3.0]oct-6-en-3-one
[CAS# 43119-28-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: (1S,5R)-2-Oxabicyclo[3.3.0]oct-6-en-3-one
• Synonyms: (3aR,6aS)-3,3a,6,6a-tetrahydrocyclopenta[b]furan-2-one
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.14
• CAS Registry Number: 43119-28-4
• EC Number: 610-106-4
• SMILES: C1C=C[C@@H]2[C@H]1OC(=O)C2

Properties

• Density: 1.196
• Melting point: 46.5 °C
• Boiling point: 263.1 °C
• Flash point: 104.0 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

(1S,5R)-2-Oxabicyclo[3.3.0]oct-6-en-3-one is an organic compound with a bicyclic structure that has been widely used in synthetic organic chemistry. The discovery of this compound and its unique molecular framework originated from studies into the synthesis of oxygen-containing bicyclic systems, which are known for their high reactivity and usefulness in constructing complex molecular architectures. These compounds, due to their strained ring systems, provide valuable intermediates in both total synthesis and medicinal chemistry.

The synthesis of (1S,5R)-2-Oxabicyclo[3.3.0]oct-6-en-3-one typically involves cyclization reactions that form the bicyclic ring system, often employing intramolecular condensation or other ring-closing strategies. The stereochemistry of the compound, indicated by the (1S,5R) designation, plays a critical role in its reactivity and application. Control over the stereochemistry is achieved through asymmetric synthesis techniques, which have been refined through decades of research into chiral reagents and catalysts.

In organic synthesis, (1S,5R)-2-Oxabicyclo[3.3.0]oct-6-en-3-one is highly valued as a building block for constructing more complex molecules. Its strained bicyclic structure makes it an ideal candidate for ring-opening reactions, which can lead to the formation of various linear or cyclic compounds. This reactivity is particularly useful in the synthesis of natural products and biologically active molecules, where intricate ring systems and precise stereochemical control are often required.

The compound is also used in pharmaceutical research, where its bicyclic core can be modified to explore new biologically active derivatives. By introducing different functional groups at strategic positions, chemists can fine-tune the physicochemical properties and biological activities of the resulting compounds. This approach has been used in the development of potential drug candidates targeting a range of therapeutic areas, including anti-inflammatory and anti-cancer agents.

In addition to its use in drug discovery, (1S,5R)-2-Oxabicyclo[3.3.0]oct-6-en-3-one has applications in material science, where it can be employed in the synthesis of polymers or as a monomer in copolymerization reactions. The rigidity and defined stereochemistry of the bicyclic structure impart desirable mechanical and thermal properties to the resulting materials, making them suitable for various industrial applications.

References

1991. Total synthesis and properties of prostaglandins 30. Modification of (1S,5R)-2-oxabicyclo[3.3.0]-6-octen-3-one at the α-carbon atom. Chemistry of Heterocyclic Compounds.
DOI: 10.1007/bf00515573

2019. Organocatalytic Baeyer-Villiger Oxidation for the Synthesis of Prostaglandins. Synfacts.
DOI: 10.1055/s-0039-1689892

2013. Cloning, overexpression and biocatalytic exploration of a novel Baeyer-Villiger monooxygenase from Aspergillus fumigatus Af293. AMB Express.
DOI: 10.1186/2191-0855-3-33