33440-68-5

Upstream product

• 35100-89-1 2-Benzyl-1,4-naphthalindiol 
• 63534-41-8 1a-benzylnaphtho[2,3-b]oxirene-2,7(1aH,7aH)-dione 
• 108-88-3 toluene 
• 130-15-4 [1,4]naphthoquinone 
• 103-45-7 acetic acid phenethyl ester 
• 103-82-2 phenylacetic acid 
• 36441-32-4 2-benzyl-1-naphthol 
• 68707-65-3 2-benzyl-1,4-dimethoxynaphthalene 
• 67-56-1 methanol 
• 613-59-2 2-benzylnaphthalene 
• 191598-16-0 2-benzyl-1,2,3,4-tetrahydro-1,4-dioxonaphthalene 
• 316801-21-5 benzyl p-methylphenyl telluride 
• 75965-83-2 1,4-dimethoxynaphthalene-2-carbaldehyde 
• 137789-68-5 2-Benzoyl-1,4-dimethoxynaphthalene 

Downstream Products

• 73377-80-7 (-)-2-Benzyl-1,4-naphthoquinone 2,3-epoxide 
• 52711-63-4 2,3-dibenzyl-1,4-naphthoquinone 
• 68749-83-7 2-Benzyl-3-ethyl-1,4-naphthochinon 
• 76055-26-0 6-benzyl-7,7a-dihydro-7,7a-dimethyldibenzofluorene-5,8,13-trione 
• 152535-74-5 2-Amino-4-benzyl-3-carbomethoxy-5-hydroxynaphtho[1,2-b]furan 
• 152535-60-9 2-amino-4-benzyl-3-cyano-5-hydroxynaphtho[1,2-b]furan 
• 150338-25-3 (2S,3R)-2-benzyl-2,3-epoxynaphthoquinone 
• 73377-80-7 (2R,3S)-2-benzyl-2,3-epoxynaphthoquinone 
• 52711-59-8 2‐benzyl‐3‐methylnaphthalene‐1,4‐dione 

Relevant academic research and scientific papers

Metal-free oxidative cross-dehydrogenative coupling of quinones with benzylic C(sp3)-H bonds

A metal-free cross-dehydrogenative coupling of quinones with toluene derivatives has been established. A series of quinones were subjected to reaction with toluene derivatives in the presence of di-tertbutyl peroxide (DTBP) for direct synthesis of benzylq

Radical Benzylation of Quinones via C-H Abstraction

Herein we report the development of radical benzylation reactions of quinones using Selectfluor and catalytic Ag(I) initiators. The reaction is believed to proceed via a C-H abstraction mechanism after Ag(I)-mediated reduction of Selectfluor. This reaction occurs under mild conditions and is effective for a variety of quinones and radical precursors bearing primary benzylic carbons. The use of preformed Ag(4-OMePy)2NO3 as a catalyst proved effective in improving the reaction efficiency by reducing unwanted degradation pathways available to Selectfluor.

The Application of 2-Benzyl-1,4-naphthoquinones as Pronucleophiles in Aminocatalytic Synthesis of Tricyclic Derivatives

This study demonstrates an unprecedented reactivity of 2-substituted-1,4-naphthoquinones. By applying the principle of vinylogy, they have been employed as vinylogous pronucleophiles in the organocatalytic cascade reaction for the first time. This novel catalytic activation of 1,4-naphthoquinones enables access to carboannulated naphthalen-1(4H)-one derivatives of biological importance. The site-selectivity and stereoselectivity of a process proved possible to control by the proper choice of reaction conditions.

Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells

Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, α- and β-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6-11.7 μM) compared to the current drug of choice cisplatin (IC 50 = 16.5 μM). This study also established that the two new synthetic halogenated compounds 12a and 16a (IC50 = 3.0 and 7.3 μM) and the previously reported compound 11a (IC50 = 3.9 μM), were non-toxic to NIH3T3 normal fibroblast cells. Cell death of oesophageal cancer cells by processes involving PARP cleavage caused by 11a was shown to be associated with elevated c-Jun levels, suggesting a role for this pathway in the mechanism of action of this cohort of naphthoquinone compounds.

Enantioselective epoxidation of 2-substituted 1,4-naphthoquinones using gem-dihydroperoxides

New gem-dihydroperoxides were successfully used for DBU-promoted enantioselective epoxidation of 2-substituted 1,4-naphthoquinones. The corresponding 1,4-naphthoquinone epoxides were obtained in yields up to 97% and ee's up to 82%.

A new synthetic route to substituted quinones by radical-mediated coupling of organotellurium compounds with quinones

Carbon-centered radicals generated from the corresponding organotellurium compounds react with a variety of quinones under photo-thermal conditions to give the monoaddition product in moderate to excellent yield. The reaction can be used for the synthesis of polyprenyl quinoid natural products and C-glycosides.

Electroorganic reactions. Part 56: Anodic oxidation of 2-methyl- and 2-benzylnaphthalenes: Factors influencing competing pathways

A systematic investigation of the anodic oxidation in nucleophilic media of 2-methyl and 2-benzylnaphthalenes, substituted at the 6-position in the naphthalene nucleus and at the 4-phenyl position of the benzylic side chain, has been carried out to identify factors favouring side-chain substitution. Cyclic voltammetry confirms that 6-substitution has a profound effect on the oxidation potentials of the naphthalene nucleus and 13C chemical shifts indicate polar effects at the benzylic carbon. However, little side-chain anodic oxidation is observed under any conditions tried; the radical-cations of electron-rich substrates preferentially dimerise and a strongly electron-withdrawing substituent at the 6-position (EtOSO2) promotes nuclear substitution. In contrast, oxidation with DDQ in aqueous acetic acid gives efficient side-chain oxidation for electron rich substrates, consistent with hydride transfer, possibly intramolecularly via a charge transfer complex.

Synthetic Studies on the Kinamycin Family of Antibiotics: Synthesis of 2-(Diazobenzyl)-p-naphthoquinone, 1,7-Dideoxy-3-demethylprekinamycin, and 1-Deoxy-3-demethylprekinamycin

2-(Diazobenzyl)-p-naphthoquinone was synthesized from 2-benzyl-1,4-dimethoxynaphthalene by cerric ammonium nitrate oxidation to 2-benzyl-p-naphthoquinone followed by diazo transfer with tosyl azide. 1,7-Dideoxy-3-demethylprekinamycin was prepared from 1,4-dimethoxynaphthalene by bromination, lithiation, and condensation with acetanthranil to give 2-(2′-N-acetaminobenzoyl)-1,4-dimethoxynaphthalene, which, following deacylation, was subjected to Pschorr cyclization to give 1,3,7-trihydro-O,O-dimethylkinafluorenone. This was then demethylated, subjected to hydrazinolysis, and then oxidized with Fetizon's reagent to complete the synthesis. 1-Deoxy-3-demethylprekinamycin was synthesized from 3-bromo-1,5-dimethoxy-4-naphthol by an identical route.

ELECTRON-TRANSFER PROCESSES: MECHANISMS OF OXIDATION OF ETHERS AND ESTERS BY SILVER-CATALYZED PEROXYDISULPHATE

Nucleophilic carbon-centred radicals, generated from the oxidation of diethyl ether, ethyl acetate, propyl acetate, ethyl propionate, diethyl oxalate and 2-phenylethyl acetate by silver-catalyzed decomposition of peroxydisulphate, have been trapped, mostly by naphthoquinone and in a few cases by protonated quinoline. Characterization of the intermediate radicals allows the rationalization of the mechanism of these oxidations, which are likely to occur through an initial electron-transfer step by Ag(II).

PHOTOCHEMICAL REACTION OF EPOXYNAPHTOQUINONE WITH AMINE. ITS DEPENDENCY ON SOLVENT STUDIED BY CIDNP TECHNIQUE

The oxirane ring of epoxynaphthoquinones was reductively opened upon irradiation in the presence of triethylamine and, in addition, a cross adduct was obtained in the reaction with N,N-dimethylaniline in benzene.CIDNP signals observed in the reaction with N,N-dimethylaniline were interpreted as evidence for hydrogen atom abstraction in benzene and for electron transfer in acetone and acetonitrile.