76149-14-9

Upstream product

• 120-80-9 benzene-1,2-diol 
• 1344113-45-6 C₁₄H₂₃IO₂Si 
• 540-38-5 p-Iodophenol 
• 71573-24-5 4-amino-1,2-benzenediol diacetate 

Downstream Products

• 3843-74-1 Methyl caffeate 

Relevant academic research and scientific papers

CYCLIC COMPOUNDS AND METHODS OF MAKING AND USING THE SAME

The present invention provides compounds, or pharmaceutically acceptable salts thereof, for inhibiting the growth of a microbe; treating a mammal having a microbial infection, mucositis, an ophthalmic infection, an otic infection, a cancer, or a Mycobacterium infection; inhibiting the growth of a Mycobacterium species; modulating an immune response in a mammal; or antagonizing unfractionated heparin, low molecular weight heparin, or a heparin/low molecular weight heparin derivative.

Hydroxylation of p-substituted phenols by tyrosinase: Further insight into the mechanism of tyrosinase activity

A study of the monophenolase activity of tyrosinase by measuring the steady state rate with a group of p-substituted monophenols provides the following kinetic information: kcatm and the Michaelis constant, KMm. Analysis of these data taking into account chemical shifts of the carbon atom supporting the hydroxyl group (δ) and σp+, enables a mechanism to be proposed for the transformation of monophenols into o-diphenols, in which the first step is a nucleophilic attack on the copper atom on the form Eox (attack of the oxygen of the hydroxyl group of C-1 on the copper atom) followed by an electrophilic attack (attack of the hydroperoxide group on the ortho position with respect to the hydroxyl group of the benzene ring, electrophilic aromatic substitution with a reaction constant ρ of -1.75). These steps show the same dependency on the electronic effect of the substituent groups in C-4. Furthermore, a study of a solvent deuterium isotope effect on the oxidation of monophenols by tyrosinase points to an appreciable isotopic effect. In a proton inventory study with a series of p-substituted phenols, the representation of kcatfn/kcatf0 against n (atom fractions of deuterium), where kcatfn is the catalytic constant for a molar fraction of deuterium (n) and kcatf0 is the corresponding kinetic parameter in a water solution, was linear for all substrates. These results indicate that only one of the proton transfer processes from the hydroxyl groups involved the catalytic cycle is responsible for the isotope effects. We suggest that this step is the proton transfer from the hydroxyl group of C-1 to the peroxide of the oxytyrosinase form (Eox). After the nucleophilic attack, the incorporation of the oxygen in the benzene ring occurs by means of an electrophilic aromatic substitution mechanism in which there is no isotopic effect.

Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C-H oxygenation

A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon-protected catechol. A routine desilylation of the silacyle with TBAF uncovers the catechol product.

Selective iodination of some phenols, anilines and methoxyarenes by molecular iodine in the presence of 1-butyl-3-methylimidazolium hydrogen sulphate

A simple, mild and regioselective method for the iodination of some phenols, anilines and methoxyarenes by using molecular iodine in presence of 1-butyl-3-methylimidazolium hydrogen sulphate ([bmim]-HSO4) in acetonitrile as solvent is reported. One-pot synthesis, mild reaction conditions, short reaction times and excellent yields of the products are noteworthy.

A green reagent for the iodination of phenols

A new reagent (I2/NaNO2) for the iodination of the aromatic ring of phenols has been discovered. The reaction proceeds at room temperature in 1.5-6 hours. In the presence of this reagent, iodinated compounds are regioselectively formed in significant yields from the corresponding substrates. Georg Thieme Verlag Stuttgart.