175226-64-9

Basic information

• Product Name: 2H-1,4-Oxazin-2-one, 5,6-dihydro-5-phenyl-, (R)-
• CAS NO: 175226-64-9
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Mol File: 175226-64-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2H-1,4-Oxazin-2-one, 5,6-dihydro-5-phenyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1,4-Oxazin-2-one, 5,6-dihydro-5-phenyl-, (R)-(175226-64-9)
• EPA Substance Registry System: 2H-1,4-Oxazin-2-one, 5,6-dihydro-5-phenyl-, (R)-(175226-64-9)

Safety Data

• Hazardous Substances Data: 175226-64-9(Hazardous Substances Data)

Upstream product

• 56613-80-0 D-2-phenylglycinol 
• 116173-81-0 (R)-2-methyl-4-phenyl-Δ²-oxazoline 

Downstream Products

• 121269-45-2 (R)-5-phenyl-3,4,5,6-tetrahydro-2H-1,4-oxazin-2-one 

Relevant articles and documents

Oxidative rearrangement of 2-substituted oxazolines. A novel entry to 5,6-dihydro-2H-1,4-oxazin-2-ones and morpholin-2-ones

A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important 'chiral glycine' synthons for asymmetric synthesis of α-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of α-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a 'nitrilium to acylium' 1,2-migration.