55077-80-0

Upstream product

• 67-56-1 methanol 
• 55077-79-7 5,8-dimethoxy-1,4-dihydronaphthalene 
• 124-41-4 sodium methylate 
• 4676-60-2 5,8-dimethoxy-1,2,3,4-tetrahydro-2H-1-naphthalenol 
• 83514-33-4 1,4-Dihydroxy-5,6-dihydronaphthalene 
• 77-78-1 dimethyl sulfate 
• 35043-92-6 cis-5,8,9,10-tetrahydronaphtho-1,4-quinone 
• 10075-62-4 1,4-dimethoxynaphthalene 
• 1015-55-0 5,8-dimethoxytetralone 
• 130-15-4 [1,4]naphthoquinone 

Downstream Products

• 74526-84-4 1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene 
• 75251-98-8 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene 
• 37464-90-7 5,8-dimethoxy-2-tetralone 
• 10075-62-4 1,4-dimethoxynaphthalene 
• 33628-85-2 (+/-)-2-acetyl-2-hydroxy-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene 
• 91575-96-1 Benzoic acid (S)-1-(5,8-dimethoxy-3,4-dihydro-naphthalen-2-yl)-ethyl ester 
• 41098-96-8 (R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

Simple and efficient synthesis of 4,7-dimethoxy-1(H)-indene

Stirring 4,7-dimethoxy-1-indanol in chloroform at room temperature in the presence of a catalytic amount of p-toluenesulfonic acid gave 4,7-dimethoxy-1(H)-indene in quantitative yield. Other solvents, including benzene, which was the most frequently used one for this reaction, gave mostly polymeric materials. The new method was also effective for dehydration of other electron-rich benzylic alcohols. Copyright Taylor & Francis Group, LLC.

Synthesis and adrenergic properties of new duplicated analogs of methoxamine

New duplicated analogs of the α1-selective agonist methoxamine and of its cyclic derivative 5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthylamine have been synthesized and tested for their adrenergic properties. All the compounds prepared, presenting a polymethylene spacer of varying length between two units of the active structure, turned out to be completely devoid of any α-stimulating activity. Surprisingly, some of them showed a marked β-adrenergic agonistic effect, being the most interesting compound active at nanomolar concentration.

Simple Preparation of β-Tetralones and β-Indanones by a 1,2-Carbonyl Group Transposition

By a four-step procedure, the ketones 3 are converted into the β-tetralones 7a-d and the β-indanones 7e, f via the intermediates 4, 5, and 6.

Total Synthesis of (+/-)-4-Demethoxydaunomycinone

2-Acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol (4), the key synthon for the total synthesis of various antitumor anthracyclinones, has been prepared either from 1,4-dimethoxynaphthalene and making use of metal-ammonia reduction or from benzoquinone and going through Diels-Alder reaction with 1,3-butadiene. 4 is then converted into (+/-)-4-demethoxydaunomycinone (3b).

A Stereoconvergent Synthesis of (+)-4-Demethoxydaunomycin

Sharpless kinetic asymmetric epoxidation on (+/-)-2-(1-hydroxyethyl)-5,8-dimethoxy-3,4-dihydronaphthalene followed by LiAlH4 reduction gave R-(-)-2-(S-1-hydroxyethyl)-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene and the undesired antipode: the former was converted into R-(-)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene while the latter was epimerized and recycled.

Synthesis and Demethylation of New 5,6,7,8-Tetrahydro-4,9-dimethoxy-1H-benzindole

The title compound 17 was prepared in good yield starting from 5,6,7,8-tetrahydro-1-naphthol (9) by an advantageous synthesis route consisting of eight steps, as indicated in Scheme 2.Demethylation by reflux heating with anhydrous aluminium chloride in dry benzene furnished 4,9-dihydroxy- and 4,9-dioxo-5,6,7,8-tetrahydro-1H-benzindoles (compounds 18 an 19, respectively).All new products were identified on the basis of spectral and analytical data.