156686-47-4

Upstream product

• 4480-47-1 t-butylglyoxal 
• 40040-81-1 2-amino-3-benzyl-5-(4-methoxyphenyl)-pyrazine 
• 123437-73-0 3-benzyl-5-(4-methoxy-phenyl)-1-oxy-pyrazin-2-ylamine 
• 151427-04-2 2-(p-methoxyphenyl)ethan-1,2-dion-1-oxime sodium salt 
• 93554-83-7 α-aminophenylpropiononitrile hydrochloride 
• 75-97-8 3,3-dimethyl-butan-2-one 

Downstream Products

• 156686-48-5 2-tert-butyl-5-(tert-butyldimethylsilylperoxy)-6-(p-methoxyphenyl)-8-benzyl-3,5-dihydroimidazo<1,2-a>pyrazin-3-one 
• 124-38-9 carbon dioxide 
• 185252-83-9 8-Benzyl-2-tert-butyl-5-hydroperoxy-6-(4-methoxy-phenyl)-5H-imidazo[1,2-a]pyrazin-3-one 

Relevant academic research and scientific papers

Low-temperature photooxygenation of coelenterate luciferin analog synthesis and proof of 1,2-dioxetanone as luminescence intermediate

Coelenterate luciferin analog having bulky tert-butyl group at the 2-position was suitable for studies on chemiluminescence under various conditions. Photooxygenation of the analog(s) at low temperature (-78°C) afforded luminous intermediates which were proved as peroxides by reduction with PPh3 with resultant loss of luminescence ability. In order to clarify these structures of accumulated luminous intermediates by means of 13C NMR, three 13C enriched analogs were synthesized at the 2, 3 and 5 positions of 3,7-dihydroimidazo[1,2-a]pyrazin-3-one skeleton in 99% enrichment with site-specificity. These 13C-enriched coelenterate luciferin analogs were photooxygenated at -78°C to form two peroxidic products as luminescent intermediates. Structures of these unstable intermediates were deduced by means of 13C NMR spectra at low temperature using substrates enriched at three sites by 13C. Photooxygenation in a mixture of CF3CD2OD and CD3OD as highly protic solvents afforded the dioxetanone and 2-hydroperoxide. These two peroxides emitted light independently at different temperatures either at 400 nm (neutral species) and/or 475 nm (anionic species) after diluting to 10-5 M in diglyme (DGM) containing acid or base.

Synthesis of a Model for the Functional Part of Photoprotein Aequorin

The unstable tert-butyl peroxide of a coeleterazine (Oplophorus luciferin) homologue was synthesized by a radical reaction.This compound is a model for a key intermediate in the bioluminescence of photoprotein aequorin.

Synthesis of silyl peroxide of coelenterazine (Oplophorus luciferin) analogue for precursor of luminescence

Unstable tert-butyldimethylsilyl peroxide of coelenterazine (Oplophorus luciferin) analogue has been synthesized by radical reaction of tert-butyldimethylsilyl hydroperoxide. This compound may be a key intermediate model in the bioluminescence and chemiluminescence of coelenterazine.