19519-86-9

Basic information

• Product Name: 1H-Azepine-2,7-dione, tetrahydro-1-methyl-
• CAS NO: 19519-86-9
• Molecular Formula: C7H11NO2
• Molecular Weight: 141.17
• Mol File: 19519-86-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Azepine-2,7-dione, tetrahydro-1-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Azepine-2,7-dione, tetrahydro-1-methyl-(19519-86-9)
• EPA Substance Registry System: 1H-Azepine-2,7-dione, tetrahydro-1-methyl-(19519-86-9)

Safety Data

• Hazardous Substances Data: 19519-86-9(Hazardous Substances Data)

Upstream product

• 2556-73-2 1-methyl-2-azepanone 

Relevant articles and documents

Chemical and microsomal oxidation of tertiary amides: Regio- and stereoselective aspects

The conformationally restricted tertiary amides N-methyl-2-pyrrolidone 6, N-methyl-2-piperidone 7 and N-methyl-ε-caprolactam 8 were oxidised by 5,10,15,20-tetraphenylporphyrinatoiron(III) chloride/tert-butyl hydroperoxide (TPPFe/ButOOH) and by phenobarbital-induced rat liver microsomes. The products were the N-demethylated lactams together with the analogous N-methylimides and norimides. For the TPPFe/ButOOH reaction ring oxidation is preferred to N-demethylation, paralleling the relative stabilities of the corresponding intermediate carbon-centred radicals as calculated by the AM1 semi-empirical method. In contrast, the microsomal reaction of the N-methyllactams strongly favours N-demethylation, demonstrating that hydrogen atom abstraction from the alkyl group Z to the amide carbonyl oxygen atom is preferred. The chiral tertiary amides N-methyl-N-(1-phenylethyl)benzamide 9 and N-methyl-5-phenyl-2-pyrrolidone 10 were also oxidised by TPPFe/ButOOH and by phenobarbital-induced rat liver microsomes. Using TPPFe/ButOOH, loss of the secondary alkyl group of 9 is preferred by a factor of ca. 6. Similarly, ring oxidation of 10 is favoured over demethylation by a factor of 9. For the microsomal reaction of (R)-9 dealkylation is preferred over demethylation by a factor of 1.7, whereas for (S)-9 demethylation is favoured by a factor of 1.25. For the microsomal reaction of (R)-10 and (S)-10 ring oxidation at the 5-position of the pyrrolidone ring is preferred over demethylation by factors of ca. 4 and 9 for the two isomers, respectively, and the (S)-enantiomer undergoes ring oxidation 2-3 times more readily than the (R)-enantiomer. For both 9 and 10 there is negligible stereochemical influence of the chiral centre upon the N-demethylation reaction. The results show that the stereochemical preference of the microsomal N-dealkylation reaction is modest.

RUTHENIUM TETROXIDE OXIDATION OF N-ALKYL-LACTAMS

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