929879-02-7

Basic information

• Product Name: 3-(ethoxymethyl)-6,6-dimethyl-4-phenyl-5,6-dihydro-4H-1,2-oxazine
• Synonyms: 3-(ethoxymethyl)-6,6-dimethyl-4-phenyl-5,6-dihydro-4H-1,2-oxazine
• CAS NO: 929879-02-7
• Molecular Weight: 247.337
• Mol File: 929879-02-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-(ethoxymethyl)-6,6-dimethyl-4-phenyl-5,6-dihydro-4H-1,2-oxazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(ethoxymethyl)-6,6-dimethyl-4-phenyl-5,6-dihydro-4H-1,2-oxazine(929879-02-7)
• EPA Substance Registry System: 3-(ethoxymethyl)-6,6-dimethyl-4-phenyl-5,6-dihydro-4H-1,2-oxazine(929879-02-7)

Safety Data

• Hazardous Substances Data: 929879-02-7(Hazardous Substances Data)

Upstream product

• 638133-04-7 6,6-dimethyl-5,6-dihydro-3-methyl-4-phenyl-1,2-oxazine N-oxide 
• 64-19-7 acetic acid 
• 638133-16-1 6,6-dimethyl-3-methylene-4-phenyl-2-(trimethylsilyloxy)-2,3,5,6-tetrahydro-4H-[1,2]oxazine 
• 141-52-6 sodium ethanolate 
• 742062-86-8 3-(bromomethyl)-6,6-dimethyl-4-phenyl-5,6-dihydro-4H-1,2-oxazine 
• 100-52-7 benzaldehyde 
• 705-60-2 1-phenyl-2-nitroprop-1-ene 

Downstream Products

• 1003867-58-0 2-acetyl-3-(ethoxymethyl)-6,6-dimethyl-4-phenyl-5,6-dihydro-2H-1,2-oxazine 

Relevant articles and documents

Addition of HO-Acids to N,N-Bis(oxy)enamines: Mechanism, Scope and Application to the Synthesis of Pharmaceuticals

The regioselectivity of the addition of HO-acids to the activated π bond in N,N-bis(oxy)enamines has been found to be dramatically dependent upon the solvent. Mechanistic investigations and quantum-chemical calculations revealed that solvent affects the reaction pathway. In basic solvents (DMF, NMP, DMSO), N,N-bis(oxy)enamines were converted into nitrosoalkenes by a Lewis base promoted process followed by oxy-Michael addition of the HO-acid. In non-polar solvents (toluene, CH2Cl2), the reaction occurs by an acid-promoted SN′ substitution of the N-oxy-group via a highly reactive N-vinyl-N-alkoxynitrenium species. Based on these studies, general and efficient protocols for the oximinoalkylation of various HO-acids (carboxylic acids, phenols, hydroxamic, phosphoric and sulfonic acids) employing readily available N,N-bis(oxy)enamines were developed. These methods proved to be applicable to the post-modification of natural molecules bearing acidic OH groups (such as steroidal hormones, bile acids, protected amino acids and peptides) and ligands (BINOL). The resulting α-oxyoximes were demonstrated to be useful precursors of valuable 1,2-amino alcohol or 1,2-hydroxylamino alcohol derivatives, including the antiarrhythmic drug Mexiletine and a potent matrix metalloproteinase inhibitor.