625-34-3Relevant articles and documents
UV Photochemistry of Acetylacetaldehyde Trapped in Cryogenic Matrices
Coussan, S.,Ferré, N.,Rousselot-Pailley, P.,Sobanska, S.
, p. 4916 - 4928 (2020)
The broad band UV photochemistry of acetylacetaldehyde, the hybrid form between malonaldehyde and acetylacetone (the two other most simple molecules exhibiting an intramolecular proton transfer), trapped in four cryogenic matrices, neon, nitrogen, argon, and xenon, has been studied by IRTF spectroscopy. These experimental results have been supported by B3LYP/6-311G++(2d,2p) calculations in order to get S0 minima together with their harmonic frequencies. On those minima, we have also calculated their vibrationally resolved UV absorption spectra at the time-dependent DFT ωB97XD/6-311++G(2d,2p) level. After deposition, only the two chelated forms are observed while they isomerize upon UV irradiation toward nonchelated species. From UV irradiation effects we have identified several nonchelated isomers, capable, in turn, of isomerizing and fragmenting, even if this last phenomenon seems to be most unlikely due to cryogenic cages confinement. On the basis of these findings, we have attempted a first approach to the reaction path of electronic relaxation. It appeared that, as with acetylacetone, the path of electronic relaxation seems to involve triplet states.
Straightforward entry into 5-hydroxy-1-aminopyrrolines and the corresponding pyrroles from 1,2-diaza-1,3-butadienes
Attanasi, Orazio A.,De Crescentini, Lucia,Favi, Gianfranco,Filippone, Paolino,Mantellini, Fabio,Santeusanio, Stefania
, p. 8178 - 8181 (2002)
The synthesis of 5-hydroxy-1-aminopyrroline-3-carboxylic acid derivatives and 5-unsubstituted-1-aminopyrrole-3-carboxylic acid derivatives from 1,2-diaza-1,3-butadienes and aldehydes is presented. These domino reactions offer the advantage of executing multistep transformation without intermediate workup procedures. The stereoselectivity of ring closure to 5-hydroxy-1-aminopyrroline-3-carboxylic acid derivatives and phenyl transposition to 2,3-diphenyl-1-aminopyrrole-3-carboxylic acid derivatives are also studied.
Reaction of alkyl- and arylamines with 2-(hydroxyimino)-3-oxobutanal
Yarofeeva,Tsutsura,Frolenko,Semichenko,Kondrasenko,Suboch
, p. 1 - 5 (2017/03/16)
The condensation of 2-(hydroxyimino)-3-oxobutanal with primary aliphatic amines, cyclohexanamine, and amines containing an adamantane fragment afforded 4-(alkylamino)- and 4-(cyclohexylamino)-3- nitrosobut-3-en-2-ones. Analogous reaction with substituted anilines RC6H4NH2 (R = H, 4-Me, 4-OMe, 4-NH2, 4-Br, 4-I, 3-NO2) led to the formation of 4-aryl-3-hydroxyiminobutan-2-ones.
Thiamine pyrophosphate stimulates acetone activation by desulfococcus biacutus as monitored by a fluorogenic ATP analogue
Gutiérrez Acosta, Olga B.,Hardt, Norman,Hacker, Stephan M.,Strittmatter, Tobias,Schink, Bernhard,Marx, Andreas
, p. 1263 - 1266 (2014/07/08)
Acetone can be degraded by aerobic and anaerobic microorganisms. Studies with the strictly anaerobic sulfate-reducing bacterium Desulfococcus biacutus indicate that acetone degradation by these bacteria starts with an ATP-dependent carbonylation reaction leading to acetoacetaldehyde as the first reaction product. The reaction represents the second example of a carbonylation reaction in the biochemistry of strictly anaerobic bacteria, but the exact mechanism and dependence on cofactors are still unclear. Here, we use a novel fluorogenic ATP analogue to investigate its mechanism. We find that thiamine pyrophosphate is a cofactor of this ATP-dependent reaction. The products of ATP cleavage are AMP and pyrophosphate, providing first insights into the reaction mechanism by indicating that the reaction proceeds without intermediate formation of acetone enol phosphate.
