(R)-4-Benzyl-3-propionyl-2-oxazolidinone, CAS No. 131685-53-5

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131685-53-5

Catalog No. EBD219618

CAS 131685-53-5

Name (R)-4-Benzyl-3-propionyl-2-oxazolidinone

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Basic Information

Synonyms: (r)-(-)-4-benzyl-3-propionyl-2-oxazolidinone n-propionyl-(4r)-benzyl-2-oxazolidinone n-3-propionyl-(4r)-benzyl-2-oxazolidinone (r)-(-)-4-benzyl-3-propiomyl-2-oxazolidinone (4r)-4-benzyl-3-propanoyl-1,3-oxazolidin-2-one (-)-4-benzyl-3-propionyl-2-oxazolidinone (4r)-4-benzyl-3-propionyl-1,3-oxazolidin-2-one (R)-4-Benzyl-3-propionyl-2-oxazolidinone (R)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone

Molecular Formula: C13H15NO3

Molecular Weight: 233.26

MDL Number: MFCD00269687

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks

Product Description:

(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone is a chiral Evans auxiliary, a class of compounds widely used in asymmetric synthesis. It is a white to off-white crystalline solid with a molecular formula of C13H15NO3. Its key structural feature is the oxazolidinone ring substituted with a benzyl group at the 4-position and a propionyl group at the 3-position, which provides a rigid framework for stereocontrol. This compound serves as a highly effective chiral auxiliary in organic synthesis, particularly for the enantioselective alkylation, aldol, and Diels-Alder reactions. It is used to introduce chirality during the synthesis of complex molecules, enabling the production of single enantiomers of pharmaceutical intermediates and active pharmaceutical ingredients (APIs). Its primary application is in the research and development of chiral drugs, where it helps construct stereogenic centers with high diastereoselectivity. As a specialized chiral building block, it is not a commodity chemical but a high-value reagent for method development and small-scale synthesis in medicinal chemistry. Proper handling is required as it may cause skin and eye irritation.

Physical Properties

Melting Point: 44-46 °C(lit.)

Boiling Point: 396.639 °C at 760 mmHg

Flash Point: 193.681 °C

Density: 1.206 g/cm3

Refractivity: -103 ° (C=1, EtOH)

Analytical Data

Appearance: white to light yellow crystal powder