(S)-(+)-4-Phenyl-2-oxazolidinone
[CAS# 99395-88-7]

Identification

• Classification: Biochemical >> Peptide
• Name: (S)-(+)-4-Phenyl-2-oxazolidinone
• Synonyms: (4S)-4-phenyl-1,3-oxazolidin-2-one
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• CAS Registry Number: 99395-88-7
• EC Number: 619-429-5
• SMILES: C1[C@@H](NC(=O)O1)C2=CC=CC=C2

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 129-132 °C (Expl.)
• alpha: 52 ° (c=2, CHCl3) (Expl.)
• Index of Refraction: 1.548, Calc.^*
• Boiling Point: 407.0±25.0 °C (760 mmHg), Calc.^*
• Flash Point: 200.0±23.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

(S)-(+)-4-Phenyl-2-oxazolidinone is a chiral organic compound that belongs to the class of oxazolidinones, which are characterized by a five-membered heterocyclic ring containing nitrogen and oxygen atoms. The (S)-enantiomer of this compound, denoted as (S)-(+)-4-phenyl-2-oxazolidinone, is specifically distinguished by its stereochemistry, where the chiral center at the 2-position of the oxazolidinone ring has a particular configuration. The presence of a phenyl group at the 4-position contributes to the compound's unique properties, making it valuable in various fields of organic chemistry, particularly in asymmetric synthesis, catalysis, and medicinal chemistry.

The discovery of (S)-(+)-4-phenyl-2-oxazolidinone is part of the broader interest in the synthesis and application of chiral molecules. Oxazolidinones are a versatile class of compounds, and their enantiomers often exhibit different physical, chemical, and biological properties. The (S)-(+)-enantiomer, with its specific stereochemistry, is of particular interest because of its potential for inducing selectivity in chemical reactions and its utility in the synthesis of complex chiral molecules. The compound was first synthesized as part of a larger effort to develop chiral building blocks for asymmetric synthesis, which aims to create molecules with a specific handedness (chirality) for applications in pharmaceuticals and other fields.

One of the primary applications of (S)-(+)-4-phenyl-2-oxazolidinone is in the field of asymmetric catalysis. As a chiral ligand, it can be used to facilitate the formation of a single enantiomer in chemical reactions that would otherwise produce a racemic mixture. The presence of the phenyl group at the 4-position enhances the steric and electronic properties of the oxazolidinone ring, enabling it to coordinate with metal centers in catalysts, such as those used in transition-metal-catalyzed reactions. This allows for greater control over reaction outcomes and the selective formation of desired chiral products. Asymmetric catalysis has become an essential tool in the synthesis of fine chemicals, pharmaceuticals, and agrochemicals, and (S)-(+)-4-phenyl-2-oxazolidinone is a valuable component in this process.

In medicinal chemistry, (S)-(+)-4-phenyl-2-oxazolidinone and its derivatives are of interest as potential intermediates in the development of bioactive molecules. Oxazolidinones are well known for their role in the synthesis of antibiotics, particularly in the development of linezolid, a drug used to treat multi-drug-resistant Gram-positive bacterial infections. While (S)-(+)-4-phenyl-2-oxazolidinone itself may not exhibit antibiotic activity, it is closely related to compounds with significant therapeutic potential. The (S)-enantiomer is often preferred in the synthesis of certain bioactive molecules due to its enhanced biological activity, making it a key building block in drug discovery and development.

The compound also finds application in materials science, particularly in the development of chiral materials for use in electronic devices and sensors. The specific molecular structure of (S)-(+)-4-phenyl-2-oxazolidinone, with its aromatic phenyl group and oxazolidinone ring, could enable the creation of materials with unique optical and electronic properties. This makes it a promising candidate for the design of advanced functional materials, such as those used in liquid crystal displays (LCDs) or other optoelectronic devices, where chirality plays a critical role in the material's properties.

In conclusion, (S)-(+)-4-phenyl-2-oxazolidinone is a highly versatile compound with important applications in asymmetric synthesis, medicinal chemistry, and materials science. Its unique chiral structure allows it to serve as a valuable building block in the synthesis of bioactive compounds and as a ligand in asymmetric catalysis, with potential uses in the development of chiral materials for advanced technologies.

References

2007. Chiral Resolution of Racemic 4-Phenyl(benzyl)-2-Oxazolidone by Use of Molecularly Imprinted Polymers. Chromatographia, 65(7).
DOI: 10.1365/s10337-007-0209-7

2009. New Generation of Modular Nucleophilic Glycine Equivalents for the General Synthesis of α-Amino Acids. Synlett, 2009(4).
DOI: 10.1055/s-0028-1087929

2013. Synthesis of the Structure Proposed for Natural Meliloester. Synthesis, 44(22).
DOI: 10.1055/s-0032-1316776