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

Description

3-Vinyloxazolidin-2-one is an organic compound characterized by its molecular formula C5H7NO2. It features a cyclic enamine structure with a five-membered ring that includes an oxygen atom and a vinyl group. 3-Vinyloxazolidin-2-one is recognized for its high versatility in chemical reactions, such as nucleophilic additions and ring-opening reactions, which makes it a valuable intermediate in the synthesis of a wide range of chemical compounds.

Uses

Used in Organic Synthesis:
3-Vinyloxazolidin-2-one serves as a reagent in organic synthesis, where its ability to participate in various chemical reactions allows for the creation of diverse chemical compounds.
Used in Pharmaceutical Production:
As a building block, 3-Vinyloxazolidin-2-one is utilized in the preparation of different pharmaceuticals. Its structural properties make it a key component in the development of new drugs.
Used in the Creation of Functional Materials:
Beyond its applications in organic synthesis and pharmaceuticals, 3-Vinyloxazolidin-2-one is also employed in the production of functional materials, where its unique chemical properties contribute to the performance of the end products.
Used in Research for Biological Activities and Pharmacological Properties:
3-Vinyloxazolidin-2-one has been the subject of studies exploring its potential biological activities and pharmacological properties, indicating its promise in various applications within the field of medicine and healthcare.

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) 
• 19853-36-2 3-(1-ethoxy-ethyl)-oxazolidin-2-one 
• 77987-49-6 benzyl 2-hydroxyethylcarbamate 
• 74-86-2 acetylene 
• 593-60-2 Vinyl bromide 
• 19853-35-1 3-(1-methoxy-ethyl)-oxazolidin-2-one 
• 108-05-4 vinyl acetate 
• 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 
• 72791-76-5 bis(2-chloroethyl)carbamic acid benzyl ester 
• 3493-62-7 3-(2-acetoxy-ethyl)-oxazolidin-2-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.