1147391-02-3

Basic information

• Product Name: (R)-4-(4-chlorophenyl)oxazolidin-2-one
• Synonyms: (R)-4-(4-chlorophenyl)oxazolidin-2-one
• CAS NO: 1147391-02-3
• Molecular Formula: C₉H₈ClNO₂
• Molecular Weight: 197.61832
• Mol File: 1147391-02-3.mol

Chemical Properties

• Boiling Point: 432.0±44.0 °C(Predicted)
• Appearance: /
• Density: 1.331±0.06 g/cm3(Predicted)
• PKA: 11.86±0.40(Predicted)
• CAS DataBase Reference: (R)-4-(4-chlorophenyl)oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-(4-chlorophenyl)oxazolidin-2-one(1147391-02-3)
• EPA Substance Registry System: (R)-4-(4-chlorophenyl)oxazolidin-2-one(1147391-02-3)

Safety Data

• Hazardous Substances Data: 1147391-02-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-4-(4-chlorophenyl)oxazolidin-2-one is used as an active pharmaceutical ingredient for its antibacterial and antifungal properties, targeting various pathogens and contributing to the development of new treatments for infectious diseases.
Used in Organic Synthesis:
(R)-4-(4-chlorophenyl)oxazolidin-2-one is used as a chiral building block in the synthesis of chiral drugs and pharmaceuticals, playing a crucial role in the development of enantiomerically pure compounds with improved therapeutic effects and reduced side effects.
Used in Asymmetric Catalysis:
(R)-4-(4-chlorophenyl)oxazolidin-2-one is used as a ligand in metal-catalyzed reactions, enhancing the selectivity and efficiency of asymmetric catalysis processes, which are essential for the production of enantiomerically pure compounds in the pharmaceutical and chemical industries.
Used in Research and Development:
(R)-4-(4-chlorophenyl)oxazolidin-2-one is used as a research compound for exploring its potential applications in various fields, including medicinal chemistry, synthetic chemistry, and materials science, contributing to the advancement of scientific knowledge and the development of innovative technologies.

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 43189-37-3 (R)-2-amino-2-(4-chlorophenyl)acetic acid 
• 1073-67-2 4-vinylbenzyl chloride 
• 917-61-3 sodium isocyanate 

Downstream Products

• 1147391-11-4 (R)-4-(4-chlorophenyl)-3-isopropyl-oxazolidin-2-one 
• 1147391-40-9 (R)-4-(4'-(2-((R)-2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)oxazolidin-2-one 

Relevant articles and documents

Stereoselective Synthesis of Enantiopure Oxazolidinones via Biocatalytic Asymmetric Aminohydroxylation of Alkenes

Chiral oxazolidinones are of significance in both medicinal and synthetic chemistry, while preparing these compounds usually involves using expensive starting materials and harsh reaction conditions. Herein, a one-pot biocatalytic cascade process was developed for stereo- and regioselective aminohydroxylation of diverse alkenes by combining styrene monooxygenase and halohydrin dehalogenase, providing an approach to enantiopure oxazolidinones. (Figure presented.).

Catalytic enantioselective synthesis of β-amino alcohols by nitrene insertion

Chiral β-amino alcohols are important building blocks for the synthesis of drugs, natural products, chiral auxiliaries, chiral ligands and chiral organocatalysts. The catalytic asymmetric β-amination of alcohols offers a direct strategy to access this class of molecules. Herein, we report a general intramolecular C(sp3)-H nitrene insertion method for the synthesis of chiral oxazolidin-2-ones as precursors of chiral β-amino alcohols. Specifically, the ring-closing C(sp3)-H amination of N-benzoyloxycarbamates with 2 mol% of a chiral ruthenium catalyst provides cyclic carbamates in up to 99% yield and with up to 99% ee. The method is applicable to benzylic, allylic, and propargylic C-H bonds and can even be applied to completely non-activated C (sp3)-H bonds, although with somewhat reduced yields and stereoselectivities. The obtained cyclic carbamates can subsequently be hydrolyzed to obtain chiral β-amino alcohols. The method is very practical as the catalyst can be easily synthesized on a gram scale and can be recycled after the reaction for further use. The synthetic value of the new method is demonstrated with the asymmetric synthesis of a chiral oxazolidin-2-one as intermediate for the synthesis of the natural product aurantioclavine and chiral β-amino alcohols that are intermediates for the synthesis of chiral amino acids, indane-derived chiral Box-ligands, and the natural products dihydrohamacanthin A and dragmacidin A.[Figure not available: see fulltext.].

BIPHENYL DERIVATIVES AS MODULATORS OF THE HISTAMINE-H3 RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO

Biphenyl derivatives of Formula (Ia) and pharmaceutical compositions thereof that modulate the activity of the H3 histamine receptor. (Ia) Compounds of the present invention and pharmaceutical compositions thereof are directed to methods useful in the treatment of histamine H3-associated disorders, such as cognitive disorders, epilepsy, brain trauma, depression, obesity, disorders of sleep and wakefulness, such as narcolepsy, shift-work syndrome, drowsiness as a side effect from a medication, maintenance of vigilance to aid in completion of tasks and the like, cataplexy, hypersomnia, somnolence syndrome, jet lag, sleep apnea and the like, attention deficit hyperactivity disorder (ADHD), schizophrenia, allergies, allergic responses in the upper airway, allergic rhinitis, nasal congestion, dementia, Alzheimer's disease, pain and the like.