175416-53-2

Basic information

• Product Name: (5R)-3-tert-butyl-5-phenyl-3,4,5,6-tetrahydro-1,4-oxazin-2-one
• Synonyms: (5R)-3-tert-butyl-5-phenyl-3,4,5,6-tetrahydro-1,4-oxazin-2-one
• CAS NO: 175416-53-2
• Molecular Weight: 233.31
• Mol File: 175416-53-2.mol

Chemical Properties

• CAS DataBase Reference: (5R)-3-tert-butyl-5-phenyl-3,4,5,6-tetrahydro-1,4-oxazin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-3-tert-butyl-5-phenyl-3,4,5,6-tetrahydro-1,4-oxazin-2-one(175416-53-2)
• EPA Substance Registry System: (5R)-3-tert-butyl-5-phenyl-3,4,5,6-tetrahydro-1,4-oxazin-2-one(175416-53-2)

Safety Data

• Hazardous Substances Data: 175416-53-2(Hazardous Substances Data)

Upstream product

• 175226-69-4 (5R)-3-tert-butyl-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one 

Downstream Products

• 1009606-13-6 (3S,5R)-4-benzyl-3-(tert-butyl)-5-phenylmorpholin-2-one 
• 139163-43-2 (S)-2-amino-3,3-dimethylbutanoic acid hydrochloride 

Relevant articles and documents

An efficient entry to optically active anti- and syn-β-amino-α- trifluoromethyl alcohols

The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF 3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-β-amino-α- trifluoromethyl alcohols. The corresponding syn d

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.