481-40-3

Usage

InChI:InChI=1/C10H8O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,11-13H

Upstream product

• 108-30-5 succinic acid anhydride 
• 108-95-2 phenol 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 6312-53-4 juglone 
• 83-56-7 1,5-dihydroxynaphthalene 

Downstream Products

• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 120-80-9 benzene-1,2-diol 
• 99-06-9 3-Carboxyphenol 
• 69-72-7 salicylic acid 
• 108-95-2 phenol 
• 860776-15-4 1-hydroxy-4,5-naphthylene phenylboronate 
• 481-42-5 5-hydroxy-2-methyl-1,4-naphthoquinone 
• 22266-99-5 2-methyl-5-methoxy-1,4-naphthoquinone 
• 51114-98-8 isosclerone 
• 39015-63-9 1,4,8-trihydroxynaphthalene-1-O-β-D-glucopyranoside 
• 4923-61-9 5-methoxynaphthoquinone 
• 86309-84-4 methyl 2-(4,5-isopropylidenedioxy-1-naphthyloxy)-4-phenylselenobutanoate 

Relevant academic research and scientific papers

Naphthalene diols: a new class of antioxidants intramolecular hydrogen bonding in catechols, naphthalene diols, and their aryloxyl radicals.

1,8-Naphthalenediol, 5, and its 4-methoxy derivative, 6, were found to be potent H-atom transfer (HAT) compounds on the basis of their rate constants for H-atom transfer to the 2,2-di(4-t-octylphenyl)-1-picrylhydrazyl radical (DOPPH*), k(ArOH/DOPPH)*, or as antioxidants during inhibited styrene autoxidation, k(ArOH/ROO)*, initiated with AIBN. The rate constants showed that 5 and 6 are more active HAT compounds than the ortho-diols, catechol, 1, 2,3-naphthalenediol, 2, and 3,5-di-tert-butylcatechol, 3. Compound 6 has almost twice the antioxidant activity, k(ArOH/ROO)* = 6.0 x 10(6) M(-)(1) s(-1), of that of the vitamin E model compound, 2,2,5,7,8-pentamethyl-6-chromanol, 4. Calculations of the O-H bond dissociation enthalpies compared to those of phenols, (deltaBDEs), of 1-6 predict a HAT order of reactivity of 2 alpha(ROO)* = 0.32, gave the expected order, since the ROO* reaction is more exothermic than the DOPPH* reaction. Compound 6 is sufficiently reactive to react directly with oxygen, and it lies off the log k(ArOH/ROO)* versus deltaBDE plot.

Synthesis of racemic frenolicin B and 5-epi-frenolicin B via intramolecular palladium-catalyzed aryloxycarbonylation

A synthesis of the pyranonaphthoquinone antibiotic (±)-frenolicin B [(±)-1] is described. Key step is the intramolecular palladium-catalyzed aryloxycarbonylation of the 2-allyl-1-naphthol derivatives 8a,b to give the tricyclic γ-lactones 6a,b. Only the former (6a) is converted successfully into (±)-deoxyfrenolicin, the immediate precursor of (±)-1.

Highly Efficient Synthesis and Structure–Activity Relationships of a Small Library of Substituted 1,4-Naphthoquinones

A platform of highly efficient synthetic methodologies has been established to access a focused library of substituted 1,4-naphthoquinones derivatives functionalized with a diversity of amino/hydroxy/alkyl groups. Furthermore, the structure–activity relationship deduced from antiproliferative activities and toxicities of this 1,4-naphthoquinone library and intracellular reactive oxygen species (ROS) level detections might warrant future potential of plumbagin (2) and compound 13 as promising basic structures to develop novel anti-cancer agents.

New synthetic method of plumbagin

The invention discloses a new synthetic method of plumbagin (PL), and relates to the technical field of medicine and chemical industry. The plumbagin becomes a study hot spot in treating rheumatoid arthritis and other domains. In recent years, literatures report that the plumbagin also has the effects of preventing bacterial and fungal and is used for the study of anticancer and anti-AIDS infection. However, the extraction rate of nature plumbagin is low, and the profit space is small; besides, the reported synthetic method of plumbagin is low in overall yield, high in cost, and not easy to acquire the raw material reagent, complex in post treatment process, and not friendly for environment; moreover, the purification process involves in column chromatography for many times. The raw material for the synthetic method of plumbagin is low in price and easy to acquire, and environment-friendly; the post treatment and purification process are simple, the yield is greatly promoted, the industrial production can be realized; meanwhile, the method provides an important reference basis for the subsequent scientific and research work.

New naphthoquinone derivatives against glioma cells

This work was aimed to the development of a set of new naphtoquinone derivatives that can act against glioma. The compounds were tested in order to find out their ability to inhibit the growth of glioma cells, and the results of these assays were correlated with electrochemical analysis and NMR-based reoxidation kinetic studies, suggesting that a redox mechanism underlies and may explain the observed biological behavior. In addition to a full description of the synthetic pathways, electrochemistry, NMR and single crystal X-ray diffraction data are provided.

An efficient multigram synthesis of juglone methyl ether

Based on the regioselective oxidation of 1,4,5-trimethoxynaphthalene by cerium (IV) ammonium nitrate, an efficient synthesis of juglone methyl ether has been achieved with high overall yield (74%) and good purity (98.6%). Compared with the reported methods, the reaction conditions are milder and the work-up of each step is much simpler. Moreover, the new strategy considerably reduces the cost in the synthesis of juglone methyl ether and is suitable for large-scale preparations.

Measurement of the Donor Strength of Substituted 1-Naphthols

The oxidation potential of various substituted naphthols is available by cyclovoltammetry.The donor strength of substituents on the oxidation potential may be explained on the base of substituent increments.When correlating the oxidation potential with the transition energy of charge transfer complexes with TCNE, 1-naphthols with 8-alkoxy substituents and naphthols without oxygen in position 8 are giving different correlation curves.The experimental values correlate well with semiempirically calculated HOMO energies.Our measurements allow to predict the oxidation potentials of hitherto unknown substituted 1-naphthols with high probality.Thus, it may be possible to synthesize 1-naphthols with a defined oxidation potential. - Key Words: Cyclovoltammetry / Charge-transfer complexes / HOMO energy / Naphthols