(S)-4-Benzyl-2-oxazolidinone
[CAS# 90719-32-7]

Identification

• Classification: Biochemical >> Peptide
• Name: (S)-4-Benzyl-2-oxazolidinone
• Synonyms: (4S)-4-benzyl-1,3-oxazolidin-2-one
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.20
• CAS Registry Number: 90719-32-7
• EC Number: 618-632-6
• SMILES: C1[C@@H](NC(=O)O1)CC2=CC=CC=C2

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 86-88 °C (Expl.)
• alpha: -64 ° (C=1, CHCl3) (Expl.)
• Melting point: 131-133 °C (Expl.)
• alpha: -55 ° (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;GHS08 Warning
• Risk Statements: H302-H373
• Safety Statements: P260-P264-P270-P273-P301+P317-P319-P330-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

(S)-4-Benzyl-2-oxazolidinone is a chiral organic compound that belongs to the class of oxazolidinones, characterized by a five-membered heterocyclic ring containing one nitrogen atom and one oxygen atom. The (S)-enantiomer refers to the specific stereochemistry of the compound, indicating the configuration at the chiral center. The addition of the benzyl group at the 4-position of the oxazolidinone ring introduces an aromatic character to the molecule, enhancing its potential reactivity and solubility. The development and application of (S)-4-benzyl-2-oxazolidinone are primarily focused on its use in synthetic chemistry and the pharmaceutical industry.

The discovery of (S)-4-benzyl-2-oxazolidinone is rooted in the ongoing interest in chiral molecules, particularly those that can be used to create optically active intermediates in synthetic processes. The chirality of the compound plays an important role in its reactivity and interaction with other molecules, which makes it a valuable building block in the synthesis of various biologically active compounds. Chiral oxazolidinones like (S)-4-benzyl-2-oxazolidinone are particularly sought after for their role in asymmetric synthesis, where they can be used to induce the formation of a specific enantiomer in a chemical reaction.

One of the main applications of (S)-4-benzyl-2-oxazolidinone is in the pharmaceutical industry, where oxazolidinones serve as key intermediates for the synthesis of a variety of bioactive molecules, including antibiotics. While (S)-4-benzyl-2-oxazolidinone itself may not directly exhibit antimicrobial activity, its structure is closely related to oxazolidinone antibiotics such as linezolid, which is used to treat multi-drug-resistant bacterial infections. The (S)-enantiomer of the oxazolidinone ring, like that found in (S)-4-benzyl-2-oxazolidinone, often demonstrates enhanced biological activity and selectivity when incorporated into therapeutic agents, making it an important chiral building block for drug development.

(S)-4-benzyl-2-oxazolidinone also plays a role as a chiral ligand in asymmetric catalysis. In this application, it is used to facilitate chemical reactions that require the selective formation of one enantiomer over another. The presence of the benzyl group enhances the steric and electronic properties of the ligand, allowing for greater control over the reaction mechanism and the stereochemistry of the products. Asymmetric catalysis is a powerful tool in organic chemistry, enabling the efficient and selective synthesis of complex molecules, including those with pharmaceutical applications.

Furthermore, the compound has potential uses in the field of materials science. The unique properties of the oxazolidinone ring and the aromatic benzyl group could lend themselves to the development of chiral materials such as liquid crystals or advanced materials with specific optical or electronic properties. Additionally, (S)-4-benzyl-2-oxazolidinone has been explored for its role in the development of molecular sensors and other functional materials where chirality plays a significant role in performance.

In conclusion, (S)-4-benzyl-2-oxazolidinone is a versatile compound with significant applications in the pharmaceutical, chemical, and materials science industries. Its importance as a chiral intermediate for the synthesis of biologically active molecules, as a ligand in asymmetric catalysis, and its potential uses in materials science underscore its relevance in modern synthetic chemistry.

References

2024. Synthesis of chiral 2-(N-Boc-azetidin-3-yl)-2-alkylpropanoic acids as novel GABA derivatives. Monatshefte für Chemie - Chemical Monthly, 155(1).
DOI: 10.1007/s00706-023-03149-1

2021. Enantioselective Synthesis of the Sex Pheromone of Lichen Moth, Miltochrista calamine, and Its Diastereomer. Synlett, 32(15).
DOI: 10.1055/s-0040-1719835

2020. Synthesis of Chiral N-Nitro-oxazolidin-2-ones and O-(β-Nitraminoalkyl) Carbamates in Liquefied 1,1,1,2-Tetrafluoroethane Medium. Synthesis, 52(16).
DOI: 10.1055/s-0040-1706762