58149-89-6

Usage

Class

Aromatic ketones

Explanation

Aromatic ketones are a class of organic compounds that contain a carbonyl group (C=O) attached to an aromatic ring. 1-(6-methoxy-1-naphthyl)ethan-1-one belongs to this class due to its structure.

Explanation

Naphthalene is a polycyclic aromatic hydrocarbon (PAH) from which 1-(6-methoxy-1-naphthyl)ethan-1-one is derived. The compound is formed by modifying the naphthalene structure.

Explanation

The methoxy group (-OCH3) is attached to the 6th position of the naphthalene ring in the compound.

Explanation

Due to its aromatic properties, 1-(6-methoxy-1-naphthyl)ethan-1-one is commonly used in the production of scented products, such as fragrances, flavors, and perfumes.

Explanation

The compound has potential uses in the pharmaceutical industry as a building block for the synthesis of various bioactive compounds, which can be used for therapeutic purposes.

Explanation

The primary role of 1-(6-methoxy-1-naphthyl)ethan-1-one is in the manufacturing of scented products, and it also has potential applications in the development of therapeutic compounds.

Derivation

Naphthalene

Methoxy group position

6

Applications

Fragrances, flavors, and perfumes

Potential applications

Pharmaceutical industry

Role

Manufacturing of scented products and potential therapeutic uses

InChI:InChI=1/C13H12O2/c1-9(14)12-5-3-4-10-8-11(15-2)6-7-13(10)12/h3-8H,1-2H3

Upstream product

• 87700-72-9 6-methoxy-1-naphthoyl chloride 
• 506-82-1 dimethylcadmium 
• 36112-61-5 6-methoxy-1-naphthoic acid 
• 35227-78-2 diethyl (ethoxymagnesio)malonate 
• 42200-95-3 4,6-dimethoxy-1-naphthylmethyl ketone 
• 917-54-4 methyllithium 
• 5309-18-2 1,7-dimethoxynaphthalene 
• 6398-50-1 6-methoxy-3,4-dihydronaphthalene-1-carbonitrile 
• 77029-01-7 6-methoxy-[1]naphthonitrile 
• 88-14-2 2-furanoic acid 
• 100-66-3 methoxybenzene 
• 83669-11-8 1-(6-methoxy-3,4-dihydronaphthalen-1-yl)ethanone 
• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 
• 2437-17-4 6-hydroxy-1-naphthoic acid 

Downstream Products

• 77029-02-8 2-(6-methoxy-1-naphthyl)-1-phenyl-2-propanol 

Relevant academic research and scientific papers

Development of new highly potent imidazo[1,2-b[pyridazines targeting Toxoplasma gondii calcium-dependent protein kinase 1

Using a structure-based design approach, we have developed a new series of imidazo[1,2-b]pyridazines, targeting the calcium-dependent protein kinase-1 (CDPK1) from Toxoplasma gondii. Twenty derivatives were thus synthesized. Structure-activity relationships and docking studies confirmed the binding mode of these inhibitors within the ATP binding pocket of TgCDPK1. Two lead compounds (16a and 16f) were then identified, which were able to block TgCDPK1 enzymatic activity at low nanomolar concentrations, with a good selectivity profile against a panel of mammalian kinases. The potential of these inhibitors was confirmed in vitro on T. gondii growth, with EC50 values of 100 nM and 70 nM, respectively. These best candidates also displayed low toxicity to mammalian cells and were selected for further in vivo investigations on murine model of acute toxoplasmosis.

Regioselective acylation of 2-methoxy naphthalene catalyzed by supported 12-Phosphotungstic acid

12-Phosphotungstic acid supported on silica gel, zirconium sulfate, and a combination of silica gel and zirconium sulfate (50% w/w) were employed as solid acid catalysts for regioselective acylation of 2-methoxynaphtalene with acetic anhydride. 1-(6-Methoxynaphthalen-2-yl)ethanone (2,6-AMN), a commercially important intermediate for production of Naproxen, was obtained with excellent selectivity (>98%) at 67-68% conversion using 12-phosphotungstic acid supported on silica gel 20% (w/w) in refluxing tetrachloroethane. The unreacted starting material can be easily separated from the product by a simple crystallization from nonane.

Asymmetric transfer hydrogenation of 1-naphthyl ketones by an ansa-Ru(II) complex of a DPEN-SO2N(Me)-(CH2)2(η 6-p-tol) combined ligand

The first second-generation designer Ru(II) catalyst 1b featuring an enantiopure N,C-(N-ethylene-N-methyl-sulfamoyl)-tethered (DPEN- κ2N,N′)/η6-toluene hybrid ligand is introduced. Using an S/C = 1000 in HCO2H-Et3N 5:2 transfer hydrogenation medium, secondary 1-naphthyl alcohols are obtained in up to >99.9% ee under mild conditions. Mechanistic factors are discussed.

A convenient conversion of substituted cyclohexenones into aryl methyl ketones

This work describes a straightforward multistep conversion of substrates containing a cyclohexenone moiety into mono-, bi- and tricyclic aryl methyl ketones in one single working process. Crucial steps are the addition of 1-ethoxyvinyllithium to the carbonyl group, followed by acid-catalyzed enol ether hydrolysis, dehydration, and dehydrogenation. Georg Thieme Verlag Stuttgart · New York.

Efficient syntheses of some 1-naphthylalkyl ketones and studies on their autooxidation in basic medium

Birch reductions of 4,6-dimethoxy-1-naphthylalkyl ketones 1 provided in fair to good yields the demethoxylated products, 6-methoxy-1-naphthylalkyl ketones 2(a-g), not easily accessible by other procedures. Autooxidation of these ketones in basic medium afforded the diketones 6(a-c), the acid 2h, and interestingly the phenol 5. Extension of this reduction to the related tricyclic ketone 8 afforded 9a, the phenolic ketone 9b; and significantly the dihydrocoumarin derivative 10 as a result of autooxidation of 9a. The mechanisms for demethoxylation and autooxidation have been discussed.