5309-18-2

Usage

Uses

Used in Organic Synthesis:
1,7-Dimethoxynaphthalene is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, facilitating the production of dyes and pigments.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical industry, 1,7-Dimethoxynaphthalene is utilized as a key component in the synthesis of certain drugs, contributing to the development of new medicinal compounds.
Used in Fragrance Industry:
As a fragrance ingredient, 1,7-Dimethoxynaphthalene is used in perfumes and cosmetics for its aromatic properties, enhancing the scent profiles of these products.
Used in Organic Light-Emitting Diodes (OLEDs):
1,7-Dimethoxynaphthalene is studied for its potential use in OLEDs due to its light-emitting capabilities when subjected to an electrical current, indicating its possible role in the advancement of display and lighting technologies.

InChI:InChI=1/C12H12O2/c1-13-10-7-6-9-4-3-5-12(14-2)11(9)8-10/h3-8H,1-2H3

Upstream product

• 105901-89-1 4,6-Dimethoxy-naphthalin-carbonsaeure-(2) 
• 575-38-2 1,7-Dihydroxynaphthalene 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 67-56-1 methanol 
• 108-24-7 acetic anhydride 
• 77746-22-6 1,7-Dimethoxy-naphthalen-2-ol 
• 67247-13-6 7-methoxynaphth-1-ol 
• 2059-68-9 4-bromo-1,7-dimethoxynaphthalene 
• 6836-19-7 7-Methoxy-1-tetralone 
• 15822-95-4 4,6-dimethoxy-[2]naphthoic acid methyl ester 

Downstream Products

• 5309-19-3 8-methoxy-2-tetralone 
• 98410-68-5 3,5-dimethoxy-2-naphthoic acid 
• 92891-05-9 5,7-Dimethoxy-3-phenyl-2,3-dihydro-cyclopenta[a]naphthalen-1-one 
• 126403-50-7 (Z)-2-(4,6-Dimethoxy-naphthalen-1-yl)-1,4-diphenyl-but-2-ene-1,4-dione 
• 69769-74-0 4,6-dimethoxy-1-naphthylbenzyl ketone 
• 58149-89-6 1-(6-methoxynaphthalen-1-yl)ethanone 
• 69769-77-3 6-methoxy-1-naphthylbenzyl ketone 
• 1449306-18-6 methyl 5-methoxy-2-[(1E,3E)-3-(5-fluoro-1,3-dimethyl-2-oxo-1,3-dihydropyrimidin-4-ylidene)-1-propenyl]benzoate 
• 1449306-19-7 methyl 5-methoxy-2-[(1E,3Z)-3-(5-fluoro-1,3-dimethyl-2-oxo-1,3-dihydropyrimidin-4-ylidene)-1-propenyl]benzoate 
• 1092963-99-9 2-acetoxymethyl-9-methoxy-1-(phenylcarbamoyl)naphtho[2,1-b]furan 

Relevant academic research and scientific papers

A New Practical Route for the Manufacture of (4aR, 10aR)-9-Methoxy-1- methyl-6-trimethylsilanyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline

Different synthetic routes to the enantiomerically pure octahydrobenzo[g]quinoline derivative JNZ092 were evaluated for their suitability to rapidly prepare a first clinical batch on a kilogram scale. On the basis of the experience of previous octahydrobenzo[g]quinoline projects a new linear synthesis of JNZ092 was established and scaled up successfully. The overall yield was increased by a factor 10 and the preparation time shortened significantly as compared to those of the medicinal chemistry route. As the key strategy all atoms of the octahydrobenzo[g]quinoline skeleton were introduced early by the reaction of the 6-lithiated 1,7-dimethoxynaphthalene with ethyl-2-cyano-3-ethoxyacrylate. As a valuable technological refinement the practicability of a chromatographic technique with repetitive feed injection for the problematic separation of the enantiomers was demonstrated.

Oxidative dimerization of 4-methoxynaphthylamines in the presence of semiconductors

Three types of 4-methoxynaphthylamines 4a-c were oxidized by treatment with metal oxides under molecular oxygen (O2). 4-Methoxy-1-naphthylamine 4a and 4,6-dimethoxy-1-naphthylamine 4b, on treatment with TiO2 under O2, gave mainly 2-amino-1,4-naphthoquinone derivatives 5a and 5b, respectively whereas 4,8-dimethoxy-1-naphthylamine 4c afforded an unique carbazole 6c as the major product.

Synthesis and antifungal activities of novel 2-aminotetralin derivatives

Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoline ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14α-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.

Synthesis and biological activity of some known and putative duloxetine metabolites

Several putative phase I duloxetine metabolites, 4-hydroxy-, 5-hydroxy-, 6-hydroxy-, 5-hydroxy-6-methoxy-, 6-hydroxy-5-methoxy-, 5,6-dihydroxy-, and 4,6-dihydroxyduloxetine were synthesized, and their phase II metabolite as glucuronide or sulfate conjugates were also synthesized. Their in vitro binding activities were compared to that of parent compound duloxetine.

Baker's Yeast Mediated Reduction of Aromatic Ring Substituted 2-Tetralones

2-Tetralones mono- and disubstituted with methoxy or hydroxy groups in the aromatic ring are hydrogenated to 2-tetralols in good yields by non-fermenting baker's yeast.The prevalent enantioform of the reduction product and its e.e. were found to depend on the substitution pattern.In one case, i.e. the biotransformation of 5-methoxy-2-tetralone into the corresponding 2-tetralol, an e.e. >/= 98percent was observed.A simple abstract model for explaining and predicting the stereochemical outcome in the yeast-mediated carbonyl reduction of 2-tetralones is proposed.

Regioselective Monomethylation of Unsymmetrical Naphthalenediols with Methanolic HCl

Treatment of naphthalene-1,3-diol and naphthalene-1,7-diol with methanol containing dry hydrogen chloride at room temperature gives exclusively 3-methoxy-1-naphthol and 7-methoxy-1-naphthol, respectively.Of the other two unsymmetrical naphthalenediols, the 1,2-isomer was unreactive and the 1,6-isomer gave a mixture of regioisomers under the same conditions.Two symmetrical diols (the 1,5- and 2,7-isomers) examined by the same procedure gave the monomethyl ethers in 60-70percent yields.

2-Amido-8-methoxytetralins: A Series of Nonindolic Melatonin-like Agents

A series of unsubstituted and methoxy-substituted 2-amidotetralins (4a-q) was prepared and evaluated for their ability to complete for 2-iodomelatonin binding to chicken retinal membranes and for their potency to inhibit the calcium-dependent release of dopamine from rabbit retina.The lead compound, 2-acetamido-8-methoxytetralin (4j), showed a moderate affinity (Ki = 46 nM) and potency (IC50 = 1.4 nM) at the melatonin receptor.The structural requirements necessary for optimal agonistic activity at the melatonin receptor are as follows.First, the amido group, which should have a small, nonbranched alkyl group, is essential for affinity, and second, the methoxy substituent at the 8-position of the 2-amidotetralin ring is essential for optimal agonistic activity at the melatonin receptor.We concluded that this series of unsubstituted and methoxy-substituted 2-amidotetralins constitutes a class of nonindolic melatonin-like agents that can be used as pharmacological tools to further characterize melatonin receptors and to elucidate the mode of action of melatonin.

Synthesis of Novel Methoxy and Hydroxy Derivatives of 2-Phenyl-1H-benzindoles

The synthesis of novel methoxy-derivatives of 2-phenyl-1H-benzindole 3 by condensation of α-naphthylamines 1 with N-phenacyl-pyridinium salts 2 is described, as well as their conversion into the corresponding hydroxy-derivatives 5.Unexpected quinoxaline derivatives 4 were obtained when in the condensation reaction the N-nitrophenacylpyridinium salts 2d,e have been used.