4271-26-5

Basic information

• Product Name: 3-vinyloxazolidin-2-one
• Synonyms: 3-vinyloxazolidin-2-one;3-Ethenyl-2-oxazolidinone;3-Vinyl-2-oxazolidinone;N-Vinyl-2-oxazolidinone;N-Vinyl-2-oxazolidone;N-Vinyloxazolidinone;3-ethenyl-1,3-oxazolidin-2-one
• CAS NO: 4271-26-5
• Molecular Formula: C₅H₇NO₂
• Molecular Weight: 113.11458
• EINECS: 224-260-1
• Mol File: 4271-26-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 132.3°Cat760mmHg
• Flash Point: 33.8°C
• Appearance: /
• Density: 1.282g/cm³
• Vapor Pressure: 8.93mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: 3-vinyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-vinyloxazolidin-2-one(4271-26-5)
• EPA Substance Registry System: 3-vinyloxazolidin-2-one(4271-26-5)

Safety Data

• Hazardous Substances Data: 4271-26-5(Hazardous Substances Data)

Usage

General Description

3-Vinyloxazolidin-2-one is an organic compound with the molecular formula C5H7NO2. It is a cyclic enamine that contains a five-membered ring with an oxygen atom and a vinyl group. 3-Vinyloxazolidin-2-one is used as a reagent in organic synthesis and as a building block for the preparation of various pharmaceuticals and functional materials. It is a highly versatile compound that can undergo a variety of chemical reactions, including nucleophilic additions and ring-opening reactions, making it an important intermediate in the production of diverse chemical compounds. In addition, 3-Vinyloxazolidin-2-one has been studied for its potential biological activities and pharmacological properties, showing promising results in various applications.

InChI:InChI=1/C5H7NO2/c1-2-6-3-4-8-5(6)7/h2H,1,3-4H2

Upstream product

• 497-25-6 dimethylenecyclourethane 
• 111-34-2 -butyl vinyl ether 
• 101973-67-5 (2-chloro-ethyl)-carbamic acid-(2-chloro-ethyl ester) 
• 74-86-2 acetylene 
• 77987-49-6 benzyl 2-hydroxyethylcarbamate 
• 593-60-2 Vinyl bromide 
• 19853-35-1 3-(1-methoxy-ethyl)-oxazolidin-2-one 
• 3356-88-5 N-(2'-hydroxyethyl)-2-oxazolidone 
• 660866-28-4 3-[(trimethylsilyl)ethynyl]-1,3-oxazolidin-2-one 
• 660866-29-5 3-ethynyl-1,3-oxazolidin-2-one 
• 19853-36-2 3-(1-ethoxy-ethyl)-oxazolidin-2-one 
• 72791-76-5 bis(2-chloroethyl)carbamic acid benzyl ester 
• 3493-62-7 3-(2-acetoxy-ethyl)-oxazolidin-2-one 
• 2508-01-2 3-(2-chloroethyl)-2-oxazolidinone 

Downstream Products

• 1101366-47-5 phenyl (E)-4-(2-oxooxazolidin-3-yl)but-3-enoate 
• 1454311-72-8 2-(3-methoxy-2-phenylcyclopent-2-en-1-yl)isoxazolidin-3-one 

Relevant articles and documents

N-Vinyl-2-oxazolidinone: New preparation methods and first uses as a dienophile

N-Vinyloxazolidinone was conveniently prepared in 73% overall yield by an easy two-step procedure based on the dehydroalkoxylation of an intermediate hemiaminal using trimethylsilyl trifluoromethanesulfonate and triethylamine. The good dienophilicity of this enecarbamate was demonstrated in several [4+2] stereo-controlled processes involving activated 1-oxabutadienes under appropriate Lewis-acid catalyzed conditions. In addition, an unexpected amido-alkylation of the title compound is described under mild conditions.

Photoredox Approach to N-Acyl-N′-aryl-N,N′-aminals Using Enamides and Their Conversion to γ-Lactams

A photoredox catalytic approach to synthetically valuable N-acyl-N′-aryl-N,N′-aminals is described. This method uses the addition of a radical precursor to enamides, with subsequent interception of the cationic iminium intermediate with an arylamine. The reaction has been shown to be compatible with electron-rich and electron-deficient arylamines, and moderate to good levels of diastereoselectivity can be attained using a chiral enamide. Furthermore, the N-acyl-N′-aryl-N,N′-aminal reaction products can be readily cyclized, providing a novel synthetic route to valuable γ-lactams.

Synthesis of N-vinyloxazolidinones and morpholines from amino alcohols and vinylsulfonium salts: Analysis of the outcome's dependence on the N-protecting group by nanospray mass spectrometry

The effect of the nature of the N-protecting group on 1,2-amino alcohols in annulation reactions with diphenylvinylsulfonium triflate has been investigated. Although tosyl and sulfinamide groups give morpholines in high yields, the use of N-Cbz leads to a high-yielding synthesis of N-vinyloxazolidinones. The reactions were monitored by nanospray MS/MS, which revealed why reactions are successful and the fate of reactive intermediates in the unsuccessful reactions.

1,3-Dipolar cycloaddition of N-substituted dipolarophiles and nitrones: Highly efficient solvent-free reaction

(Chemical Equation Presented) New isoxazolidines were synthesized in good to excellent yields by 1,3-dipolar cycloaddition of N-vinylamide dipolarophiles and nitrones. Strikingly, solvent-free conditions gave high conversion and yields, shortened reaction time, and minimized degradation products. N-Vinyloxazolidin-2-one and its analogues used in these cycloaddition reactions were conveniently prepared in excellent yields by a modified version of Buchwald's one-step copper-catalyzed vinylation using vinyl bromide. From the adducts, a two-step access to various unsymmetric aspartate derivatives was also described.