(-)-Corey lactone 4-phenylbenzoate alcohol
[CAS# 31752-99-5]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Prostaglandins
• Name: (-)-Corey lactone 4-phenylbenzoate alcohol
• Synonyms: (3aalpha,4alpha,5beta,6aalpha)-(-)-Hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl 1,1'-biphenyl-4-carboxylate; (3aR,4S,5R,6aS)-(-)-Hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl 1,1'-biphenyl-4-carboxylate
• Molecular Formula: C₂₁H₂₀O₅
• Molecular Weight: 352.39
• CAS Registry Number: 31752-99-5
• EC Number: 608-667-5
• SMILES: C1[C@H]2[C@H](CC(=O)O2)[C@H]([C@@H]1OC(=O)C3=CC=C(C=C3)C4=CC=CC=C4)CO

Properties

• Melting point: 128-134 ºC
• alpha: -89 º (c=1, CHCl3)
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

(-)-Corey lactone 4-phenylbenzoate alcohol is a synthetic derivative of Corey lactone, which originates from the work of renowned chemist E.J. Corey. The discovery of this compound is closely tied to Corey's pioneering efforts in the field of organic synthesis, particularly in stereocontrolled reactions and enantioselective synthesis. (-)-Corey lactone itself serves as a versatile intermediate in synthesizing a range of biologically active compounds, and the modification to form the 4-phenylbenzoate ester introduces additional chemical functionality that enhances its reactivity and application potential.

The synthesis of (-)-Corey lactone 4-phenylbenzoate alcohol involves the esterification of Corey lactone with 4-phenylbenzoic acid, typically using a coupling agent such as dicyclohexylcarbodiimide (DCC) to form the ester bond. The alcohol group remains intact, providing a reactive site for further chemical modifications or interactions. The stereochemistry of the molecule, which originates from the chiral Corey lactone, plays a crucial role in determining its chemical properties and potential applications.

In terms of application, (-)-Corey lactone 4-phenylbenzoate alcohol has been used in asymmetric synthesis, particularly in the formation of complex natural products and pharmacologically relevant molecules. Its chiral nature and functional groups allow it to serve as a building block in constructing stereochemically rich molecules, which are essential in the development of drugs and other bioactive compounds. The 4-phenylbenzoate group introduces aromatic character to the molecule, which can influence its electronic properties and interactions in organic synthesis.

The compound is also studied in the context of catalysis, where its chiral core can induce enantioselectivity in reactions. This makes (-)-Corey lactone 4-phenylbenzoate alcohol a valuable tool in the field of asymmetric catalysis, where precise control over the stereochemistry of the products is required. It has been employed in the synthesis of several key intermediates in pharmaceuticals, including prostaglandins and other biologically active molecules.

The versatility of (-)-Corey lactone 4-phenylbenzoate alcohol in organic synthesis showcases its importance in modern chemistry. Its role as an intermediate in the production of complex natural products and its utility in asymmetric catalysis highlight its significant contribution to the advancement of synthetic methods.

References

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2024. Preservative-Free Fixed Combination of Tafluprost 0.0015% and Timolol 0.5% for Treatment-Naive Patients with Open-Angle Glaucoma. Korean journal of ophthalmology: KJO.
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