17016-85-2

Basic information

• Product Name: (S)-4-Isobutyl-2-Oxazolidinone
• Synonyms: (4S)-4-Isobutyl-2-oxazolidinone;(S)-4-Isobutyloxazolidin-2-one
• CAS NO: 17016-85-2
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.18
• Mol File: 17016-85-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 300.9±9.0 °C(Predicted)
• Appearance: /
• Density: 0.999±0.06 g/cm3(Predicted)
• PKA: 12.84±0.40(Predicted)
• CAS DataBase Reference: (S)-4-Isobutyl-2-Oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-Isobutyl-2-Oxazolidinone(17016-85-2)
• EPA Substance Registry System: (S)-4-Isobutyl-2-Oxazolidinone(17016-85-2)

Safety Data

• Hazardous Substances Data: 17016-85-2(Hazardous Substances Data)

Usage

General Description

(S)-4-Isobutyl-2-Oxazolidinone is a chemical compound that belongs to the oxazolidinone class. It is an enantiomer of 4-Isobutyl-2-Oxazolidinone and is commonly used as a chiral auxillary in organic synthesis. (S)-4-Isobutyl-2-Oxazolidinone is known for its ability to facilitate asymmetric reactions, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. It is also used as a resolving agent and as a chiral ligand in various catalytic processes. Additionally, (S)-4-Isobutyl-2-Oxazolidinone has applications in the pharmaceutical industry as a key intermediate in the synthesis of chiral pharmaceuticals and agrochemicals. Overall, this compound plays a crucial role in the advancement of asymmetric synthesis and the production of important chemicals and pharmaceuticals.

Upstream product

• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 
• 124-38-9 carbon dioxide 
• 332-25-2 4-(trifluoromethoxy)benzonitrile 
• 616-38-6 carbonic acid dimethyl ester 
• 530-62-1 1,1'-carbonyldiimidazole 
• 6216-61-1 (S)-(-)-N-(benzyloxycarbonyl)leucinol 
• 2018-66-8 Z-Leu-OH 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 61-90-5 L-leucine 
• 98-59-9 p-toluenesulfonyl chloride 
• 105-58-8 Diethyl carbonate 

Downstream Products

• 204718-93-4 (S)-4-Isobutyl-3-phenylacetyl-oxazolidin-2-one 
• 155727-84-7 (4S)-4-isobutyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 
• 1542980-49-3 3-[(1R,2S,4S)-7-benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carbonyl]-(4S)-(2-methylpropyl)-2-oxazolidinone 
• 1542980-63-1 3-[(1S,2R,4R)-7-benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carbonyl]-(4S)-(2-methylpropyl)-2-oxazolidinone 
• 1232977-24-0 (S)-4-isobutyl-3-(phenylethynyl)oxazolidin-2-one 
• 110577-91-8 (S)-3-((R)-2-Hydroxy-2-p-tolyl-pent-4-enoyl)-4-isobutyl-oxazolidin-2-one 
• 204718-94-5 (2S,3S)-1,4-Bis-((S)-4-isobutyl-2-oxo-oxazolidin-3-yl)-2,3-diphenyl-butane-1,4-dione 

Relevant articles and documents

Sequencing of Sequence-Defined Oligourethanes via Controlled Self-Immolation

Sequence-defined polymers show promise for biomimetics, self-assembly, catalysis, and information storage, wherein the primary structure begets complex chemical processes. Here we report the solution-phase and the high-yielding solid-phase syntheses of discrete oligourethanes and methods for their self-immolative sequencing, resulting in rapid and robust characterization of this class of oligomers and polymers, without the use of MS/MS. Crucial to the sequencing is the inherent reactivity of the terminal alcohol to "unzip" the oligomers, in a controlled and iterative fashion, releasing each monomer as a 2-oxazolidinone. By monitoring the self-immolation reaction via LC/MS, an applied algorithm rapidly produces the sequence of the oligourethane. Not only does this process provide characterization of structurally complex molecules, it works as a reader of molecular information.

N-Acylation of Oxazolidinones via Aerobic Oxidative NHC Catalysis

The first N-acylation of synthetically useful oxazolidinones with aldehydes using aerobic oxidative NHC catalysis is reported. The reaction offers a broad scope of functionalized oxazolidinones in good to excellent yields. Careful choice of electron transfer mediators proved pivotal to achieve efficient aerobic N-acylation, which has previously proven difficult using NHC catalysis. The methodology allows a mild entry to acylated oxazolidinones, avoiding the use of hazardous and reactive prefunctionalized substrates.

Catalytic fluoride triggers dehydrative oxazolidinone synthesis from CO2

Herein, catalytic fluoride (F-) is demonstrated to be a trigger for dehydrative immobilization of atmospheric pressure CO2, such that reaction of CO2 with β-amino alcohols derived from natural amino acids gives optically pure oxazolidinones in high yields. A synergistic combination of fluoride and organosilicon agents (e.g., Bu4NF + Ph3SiF or siloxanes) enhances the catalytic activity and functional group compatibility. This system lies at the interface between homogenous and heterogeneous catalysis, and may prove useful for the development of recoverable/reusable siloxane-based CO2 immobilization materials. This journal is