Design of New Photoactivatable Amino Acids: Stereoselective Synthesis of N-Protected Phenylalanine Derivatives as Precursors of p-Diazocyclohexadienone-Containing Peptides was written by Dugave, C.. And the article was included in Journal of Organic Chemistry in 1995.Electric Literature of C7H7NO4 This article mentions the following:
4-Diazocyclohexa-2,5-dienone-based amino acids I were designed for building up photoactivatable peptides. Their stable precursors II [R = Me3CO2C (Boc), 9-fluorenylmethoxycarbonyl (Fmoc)] were synthesized by stereoselective alkylation of the corresponding benzyloxynitrobenzyl iodides by a chiral glycine equivalent Alkylation was carried out using either butyllithium in dry organic solvents or a phase transfer procedure. Alkylation, hydrolysis of the adduct, and protection as Boc and Fmoc derivatives were achieved in 57-73% overall yields and led to 97-99% optically pure material. II were inserted in model dipeptides by a homogeneous solution procedure and by solid-phase peptide synthesis. Deprotection and diazotization of the resulting p-hydroxyanilines gave the corresponding photoactivatable 4-diazocyclohexa-2,5-dienone-containing peptides in quant. yields. Such photoprobes are stable for several hours in the dark but are rapidly photolyzed at 350 nm or at 295 nm by a tryptophan-mediated energy transfer activation process. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9Electric Literature of C7H7NO4).
3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Electric Literature of C7H7NO4
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts