102441-95-2

Basic information

• Product Name: dibenzyl 3,6-dimethylpyrazine-2,5-dicarboxylate
• Synonyms: dibenzyl 3,6-dimethylpyrazine-2,5-dicarboxylate
• CAS NO: 102441-95-2
• Molecular Weight: 376.412
• Mol File: 102441-95-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: dibenzyl 3,6-dimethylpyrazine-2,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dibenzyl 3,6-dimethylpyrazine-2,5-dicarboxylate(102441-95-2)
• EPA Substance Registry System: dibenzyl 3,6-dimethylpyrazine-2,5-dicarboxylate(102441-95-2)

Safety Data

• Hazardous Substances Data: 102441-95-2(Hazardous Substances Data)

Upstream product

• 99855-38-6 2-amino-acetoacetic acid benzyl ester; hydrochloride 
• 13984-53-7 methyl 4-acetyl-5-oxohexanoate 
• 5396-89-4 benzyl acetoacetate 
• 27331-98-2 benzyl (Z/E)-2-hydroxyimino-3-oxobutanoate 

Relevant articles and documents

CaC-Ene-Reductases Reduce the CaN Bond of Oximes

Although enzymes have been found for many reactions, there are still transformations for which no enzyme is known. For instance, not a single defined enzyme has been described for the reduction of the CaN bond of an oxime, only whole organisms. Such an enzymatic reduction of an oxime may give access to (chiral) amines. By serendipity, we found that the oxime moiety adjacent to a ketone as well as an ester group can be reduced by ene-reductases (ERs) to an intermediate amino group. ERs are well-known enzymes for the reduction of activated alkenes, as of α,β-unsaturated ketones. For the specific substrate used here, the amine intermediate spontaneously reacts further to tetrasubstituted pyrazines. This reduction reaction represents an unexpected promiscuous activity of ERs expanding the toolkit of transformations using enzymes.

Synthesis of pyrazine via chemoselective reduction of β-keto-α-oximino ester using baker's yeast

The synthesis of pyrazines by the baker's yeast-mediated reaction of β-keto-α-oximino esters and amides is described. Baker's yeast reduced oximes selectively over ketones of β-keto-α-oximino esters to give the corresponding β-keto-α-amino ester intermediates, which underwent spontaneous dimerization followed by air-induced aromatization to yield pyrazines. The chemoselective reduction of β-keto-α-oximino amides using baker's yeast also afforded the corresponding pyrazines. Interestingly, both hydroximes and alkoximes gave the pyrazines by the baker's yeast-mediated reduction via the corresponding amino ketones, the known precursors of pyrazines. The reaction was strongly dependent upon pH of reaction medium, and gave optimum yields at pH 5. These results demonstrate that pyrazines were synthesized efficiently and eco-friendly using a whole-cell biocatalytic system as an alternative to chemical reduction.