cas 1611-03-6, 3,5-DI-TERT-BUTYL-4-HYDROXYPHENYLACETIC ACID | Articles data ｜lookchem

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1611-03-6

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Mechanism of photosolvolytic rearrangement of p-hydroxyphenacyl esters: Evidence for excited-state intramolecular proton transfer as the primary photochemical step
The photosolvolytic rearrangement of a variety of p-hydroxyphenacyl esters and related compounds 7-16 has been studied in solutions with up to 50% aqueous content, using product studies, triplet quenchers, and nanosecond laser flash photolysis. The p-hydroxyphenacyl moiety has recently been proposed as a new and efficient photoactivated protecting group in aqueous solution. Practical applications have been demonstrated, but much less is known about the mechanism of photoreaction. Our data support a novel mechanism in which the primary photochemical step from the singlet excited state is formal intramolecular proton transfer from the phenolic proton to the carbonyl oxygen of the distal ketone, mediated by solvent water, to generate the corresponding p-quinone methide phototautomer. This reactive intermediate (most likely in its excited state) subsequently expels the carboxylic acid with concerted rearrangement to a spiroketone intermediate, which subsequently leads to the final observed product, p- hydroxyphenylacetic acid. An alternative mechanism is deprotonation of the phenolic proton, loss of the carboxylate, and rearrangement to the spiroketone, all in one concerted primary photochemical step from S1.
Zhang, Kai,Corrie, John E. T.,Munasinghe, V. Ranjit N.,Wan, Peter
p. 5625 - 5632
(2007/10/03)

Dual inhibition of human leukocyte elastase and lipid peroxidation: In vitro and in vivo activities of azabicyclo[2.2.2]octane and perhydroindole derivatives
A series of potent and selective human leukocyte elastase (HLE) inhibitors of the Val-Pro-Val type has been developed. Initially, the central proline residue was replaced by nonnatural amino acids Phi ((2S,3aS,7aS)- perhydroindole-2-carboxylic acid) and A
Portevin, Bernard,Lonchampt, Michel,Canet, Emmanuel,De Nanteuil, Guillaume
p. 1906 - 1918
(2007/10/03)

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Chemical Properties

Melting Point: 157 °C
Boiling Point: 348.9°Cat760mmHg
Flash Point:179°C
Density: 1.063g/cm³
Vapor Pressure: 1.83E-05mmHg at 25°C
PKA: 4.51±0.10(Predicted)
PSA: 57.53000
LogP: 3.61430

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