31108-44-8

Basic information

• Product Name: 2-Oxazolidinone, 4-methylene-3-phenyl-
• CAS NO: 31108-44-8
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Mol File: 31108-44-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 4-methylene-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 4-methylene-3-phenyl-(31108-44-8)
• EPA Substance Registry System: 2-Oxazolidinone, 4-methylene-3-phenyl-(31108-44-8)

Safety Data

• Hazardous Substances Data: 31108-44-8(Hazardous Substances Data)

Upstream product

• 3422-02-4 N-(benzyloxycarbonyl)aniline 
• 103-71-9 phenyl isocyanate 
• 25209-81-8 2,3-dibromopropyl phenylcarbamate 
• 25209-80-7 2,3-dichloropropyl phenylcarbamate 
• 107-19-7 propargyl alcohol 
• 5416-67-1 2-propynyl phenylcarbamate 

Downstream Products

• 1127518-02-8 3,6-diphenyl-1,8-dioxa-2,6-diazaspiro[4.4]non-2-en-7-one 
• 29200-05-3 4-(4-nitro-benzoyloxymethyl)-3-phenyl-3H-oxazol-2-one 
• 29200-07-5 4-acetoxymethyl-4-benzoyloxy-3-phenyl-oxazolidin-2-one 
• 29200-06-4 3-phenyl-4-(phenylcarbamoyloxy-methyl)-3H-oxazol-2-one 
• 29200-01-9 4-benzoyloxymethyl-3-phenyl-3H-oxazol-2-one 
• 29200-00-8 4-benzoyloxymethyl-4-hydroxy-3-phenyl-oxazolidin-2-one 
• 52512-35-3 4-hydroxy-4-phenethyl-3-phenyl-oxazolidin-2-one 
• 52512-32-0 6a-methyl-2,6-diphenyl-3ξ-(2,4,6-trimethyl-phenyl)-(3ar,6ac)-tetrahydro-oxazolo[5,4-d]isoxazol-5-one 
• 52512-34-2 3t-benzoyl-6a-methyl-2,6-diphenyl-(3ar,6ac)-tetrahydro-oxazolo[5,4-d]isoxazol-5-one 
• 52512-30-8 6a-methyl-2,3t,6-triphenyl-(3ar,6ac)-tetrahydro-oxazolo[5,4-d]isoxazol-5-one 
• 52512-37-5 4-(2-oxo-2-phenyl-ethyl)-3-phenyl-3H-oxazol-2-one 
• 52512-38-6 5-benzoyl-4-methyl-3-phenyl-3H-oxazol-2-one 
• 56412-91-0 4H-5,13-dimethyl-1-phenyl-1-aza-3,7-dioxa-dicyclopenta--quinolin-2,8-diene 
• 56412-92-1 4-methyl-3-phenyl-5-<4'-methyl-3'-phenyl-oxazolidin-2'-on-4'-il>-Δ⁴-oxazolin-2-one 

Relevant articles and documents

Comparison between Conventional and Nonconventional Methods for the Synthesis of Some 2-Oxazolidinone Derivatives and Preliminary Investigation of Their Inhibitory Activity Against Certain Protein Kinases

A series of propargyl and allyl carbamates were prepared directly from propargyl and allyl alcohols and phenyl or cyclohexyl isocyanate or indirectly by generating the isocyanates in situ from the corresponding Cbz-protected amines. The obtained carbamate

Base catalyzed cyclization of N-aryl and N-alkyl-O-propargyl carbamates to 4-alkylidene-2-oxazolidinones

The base catalyzed cyclization of N-aryl and N-alkyl-O-propargyl carbamates is studied in detail. The effect of various bases and solvents on the efficacy of this cyclization reaction is analyzed and a new base-solvent system (LiOH in DMF) for effective cyclization of these carbamates is reported. A number of differentially substituted O-propargyl carbamates were cyclized to the corresponding 2-oxazolidinones under these conditions. The reaction conditions reported here are mild and no side reactions were observed in any of the substrates studied. A propargyl carbonate group was unaffected during the course of the cyclization of the O-propargyl carbamate group. The propargyl carbamates were prepared from the corresponding alkyl or aryl amines and the corresponding propargyl chloroformate, resulting in oxazolidinones diversely substituted at the nitrogen atom. N-Aryl-O-propargyl carbamates cyclized readily to the corresponding oxazolidinones with LiOH in DMF, whereas N-alkyl-O-propargyl carbamates reacted slowly under the same conditions. O-Propargyl carbamates substituted at the 1-position tend to cyclize faster whereas those substituted at 3-position cyclize considerably slower than the unsubstituted carbamates.

Convenient synthesis of 4-methylene-2-oxazolidinones and 4-methylenetetrahydro-1,3-oxazin-2-ones via transition-metal catalyzed intramolecular addition of nitrogen atom to actylenic triple bond

2-Propynyl tosylcarbamates 1 undergo cyclization smoothly by the catalysis of CuCl/Et3N or AgNCO/Et3N to furnish 4-methylene-2-oxazolidinones 2 in good yields. The similar cyclization of the N-acyl derivatives of 1 (PhCO, MeCO, EtOCO, etc.) is catalyzed effectively by AgNCO/t-BuOK. These reactions accommodate a variety of substituents at C1 and C3 of 2-propyn-1-ol and provide (Z)-2 as single stereoisomers. The scope of the cyclization of 3-butynyl carbamates is rather limited, and in general only N-tosyl derivatives of terminally unsubstituted 3-butyn-1-ols undergo cyclization to give 4-methylenetetrahydro-1,3-oxazin-2-ones in synthetically useful yields by the catalysis of AgNCO/Et3N or AgNCO/t-BuOK.