644-17-7

Usage

InChI:InChI=1/C7H6O3/c8-4-5-3-6(9)1-2-7(5)10/h1-3,8H,4H2

Upstream product

• 495-08-9 gentisyl alcohol 
• 41951-76-2 2-hydroxy-5-methoxybenzyl alcohol 
• 39510-96-8 2-(2,4-dioxapentyl)-p-benzoquinone 
• 90-01-7 salicylic alcohol 
• 620-24-6 3-Hydroxybenzyl alcohol 
• 150-76-5 4-methoxy-phenol 
• 27060-75-9 4-bromo-3-methylanisole 
• 1447933-44-9 2-(2-bromomethyl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 33524-31-1 2,5-dimethoxybenzyl alcohol 

Downstream Products

• 495-08-9 gentisyl alcohol 
• 50827-59-3 Methyl-carbamic acid 3,6-dioxo-cyclohexa-1,4-dienylmethyl ester 

Relevant academic research and scientific papers

Regioselective synthesis of gentisyl alcohol-type marine natural products

Gentisyl alcohol-type natural products, possessing various important biological properties, have been synthesized from 4-methoxyphenol by using a selective phenol monohydroxymethylation/monochlorination, a CAN oxidation and a sodium dithionite reduction as the key steps. The natural product synthesis is efficient, atom- and step-economical, and requires no protecting groups.

Preparation method of sateripol compounds

The invention relates to a preparation method of sateripol compounds, and belongs to the field of chemical synthesis. 4-alkoxy saligenol compounds are prepared by carrying out a reaction of 4-alkoxy phenol compounds and aldehyde ketone compounds, the gent

Substituent effects on oxidation-induced formation of quinone methides from arylboronic ester precursors

A series of arylboronic esters containing different aromatic substituents and various benzylic leaving groups (Br or N+Me3Br -) have been synthesized. The substituent effects on their reactivity with H2O2 and formation of quinone methide (QM) have been investigated. NMR spectroscopy and ethyl vinyl ether (EVE) trapping experiments were used to determine the reaction mechanism and QM formation, respectively. QMs were not generated during oxidative cleavage of the boronic esters but by subsequent transformation of the phenol products under physiological conditions. The oxidative deboronation is facilitated by electron-withdrawing substituents, such as aromatic F, NO2, or benzylic N+Me 3Br-, whereas electron-donating substituents or a better leaving group favor QM generation. Compounds containing an aromatic CH 3 or OMe group, or a good leaving group (Br), efficiently generate QMs under physiological conditions. Finally, a quantitative relationship between the structure and activity has been established for the arylboronic esters by using a Hammett plot. The reactivity of the arylboronic acids/esters and the inhibition or facilitation of QM formation can now be predictably adjusted. This adjustment is important as some applications may benefit and others may be limited by QM generation. Tunable quinone methide formation: Aromatic substituents and the benzylic leaving group strongly affect the H 2O2-induced formation of quinone methides (QMs) from arylboronic esters (see scheme). The reactivity of arylboronic esters can be predictably adjusted by varying substituents. Copyright

SYNTHETIC NANOCARRIERS WITH REACTIVE GROUPS THAT RELEASE BIOLOGICALLY ACTIVE AGENTS

This invention relates to compositions, and related compounds and methods, of conjugates of synthetic nanocarriers, or components thereof, and biologically active agents, such as immunomodulatory agents, antigens, anticancer agents or antiviral agents. The biologically active agents are released from the synthetic nanocarriers in the presence of a reducing agent or by reaction with a thiol.

μ-oxo-bridged hypervalent iodine(III) compound as an extreme oxidant for aqueous oxidations

We have found that in aqueous oxidations the -oxo-bridged hypervalent iodine trifluoroacetate reagent 1 {[(PhI(OCOCF]} is generally more reactive than the corresponding monomeric reagent, especially toward phenolic substrates. -Oxo-bridged 1 in aqueous media thus provided dearomatized quinones 3 in excellent yields in most cases compared to conventional phenyliodine(III) diacetate and bis(trifluoroacetate), as a result of the rapid oxidation of both phenols and naphthols 2. Furthermore, the oxidation reactions proceeded even in water using water-soluble -oxo oxidant 1, which has promise for -oxo-bridged reagent 1 to become the favored reagent over hydrophobic phenyliodine(III) diacetate and bis(trifluoroacetate). Georg Thieme Verlag Stuttgart New York.

An efficient catalytic oxidation of p-alkoxypenols to p-quinones using tetrabutylammonium bromide and oxone

A catalytic oxidation of p-alkoxyphenols was developed using tetrabutylammonium bromide (TBAB) and Oxone. The reaction of p-alkoxyphenol (1) with a catalytic amount of TBAB in the presence of Oxone as a cooxidant in acetonitrile-water (2 : 1) gave the corresponding p-quinone (2) in excellent yield without special treatment.

Access to functionalized quinones via the aromatic oxidation of phenols bearing an alcohol or olefinic function catalyzed by supported iron phthalocyanine

The controlled oxidation at only one position of compounds with several oxidizable sites, while keeping the other sites intact, has been demonstrated for phenols bearing alcohol or olefinic functional groups. Iron tetrasulfophthalocyanine supported on silica was found to be an efficient catalyst for the preparation of functionalized quinones under mild conditions, with tert-butylhydroperoxide as the oxidant. A novel rapid and mild one-pot procedure for the covalent grafting of iron tetrasulfophthalocyanine onto silica has been developed. The supported catalyst was characterized by chemical analysis, a specific surface study, UV-vis spectroscopy and XPS. A non-radical mechanism for this unusual selective oxidation has been revealed by 18O labelling experiments. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Anodic Oxidation of Mono- and Disubstituted 1,4-Dimethoxybenzenes

The electrochemical oxidation of mono- and disubstituted 1,4-dimethoxybenzene derivatives with zero, one, and two benzylic CH2X groups (X = OAc, Cl, OH) (5a-c and 6a-c) has been carried out by using both constant-current and controlled-potential techniques in methanol and in the presence of different electrolytes and working electrodes. Constant-current electrolysis in KOH-methanol solutions yielded mostly the corresponding 1,4-quinone derivatives from 5a-c and 6b, whereas the disubstituted 1,4-dimethoxybenzenes 6a,c underwent side-chain oxidation to form 2,5-dimethoxyterephthalaldehydes. Upon alteration of the medium from the commonly used basic KOH-methanol to neutral LiClO4-methanol, a new spectrum of products was achieved in most cases, involving novel coupling products from monosubstituted substrates and quinone derivatives from disubstituted ones. Controlled-potential oxidation at the glassy carbon anodes and in a neutral LiClO4-methanol medium led to more complex mixtures of products, namely, polymers and new coupling products from monosubstituted substrates and quinones and side-chain oxidation (or substitution) products from the disubstituted ones. Three new coupling products were isolated and characterized by X-ray measurements.

Development of new and efficient polymer-supported hypervalent iodine reagents

The aminomethylpolystyrene-supported (diacetoxyiodo)benzene reagents 4a and 4b were prepared for the first time. Using these reagents several hydroquinones and phenols can be oxidized to the corresponding quinones. Spirocyclization of phenylacetic acid and of N-protected tyrosine derivatives could also be accomplished.

Polymer-supported hypervalent iodine reagents in 'clean' organic synthesis with potential application in combinatorial chemistry

A clean oxidation reaction of a variety of substrates using polymer-supported (diacetoxyiodo)benzene (PSDIB) which proceeds in high to excellent yield with maximum purity is described including isolation and regeneration of the polymer reagent.