55077-79-7

Usage

Uses

Used in Organic Synthesis:
5,8-DIMETHOXY-1,4-DIHYDRO-NAPHTHALENE is used as a synthetic building block for the creation of various organic compounds. Its chemical structure allows it to be a versatile intermediate in the synthesis of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Fragrance Industry:
5,8-DIMETHOXY-1,4-DIHYDRO-NAPHTHALENE is used as a fragrance ingredient for its distinct orange oil scent. It is employed in the formulation of perfumes, colognes, and other fragrance products to provide a unique and pleasant aroma.
Used in Chemical Research:
5,8-DIMETHOXY-1,4-DIHYDRO-NAPHTHALENE is used as a research compound in academic and industrial laboratories. Its properties make it an interesting subject for studying various aspects of organic chemistry, such as reaction mechanisms, stereochemistry, and the development of new synthetic methods.
Used in Pharmaceutical Industry:
5,8-DIMETHOXY-1,4-DIHYDRO-NAPHTHALENE is used as a key intermediate in the synthesis of certain pharmaceutical compounds. Its unique structure can be modified to create new drug candidates with potential therapeutic applications.
Used in Dye and Pigment Industry:
5,8-DIMETHOXY-1,4-DIHYDRO-NAPHTHALENE is used as a starting material for the production of dyes and pigments. Its chemical properties allow for the creation of a variety of colored compounds that can be used in various applications, such as inks, paints, and plastics.

Upstream product

• 3090-45-7 5,8-dihydro-1,4-naphthalenediol 
• 113575-83-0 4-[Methyl(1,2,3,4-tetrahydro-2-naphthalenyl)amino]phenol, acetate ester 
• 106-51-4 p-benzoquinone 
• 6271-40-5 4a,5,8,8a-tetrahydro-1,4-naphthoquinone 
• 77-78-1 dimethyl sulfate 
• 106-99-0 buta-1,3-diene 
• 35043-92-6 cis-5,8,9,10-tetrahydronaphtho-1,4-quinone 
• 10075-62-4 1,4-dimethoxynaphthalene 
• 651777-83-2 2,3-diallylhydroquinone dimethyl ether 

Downstream Products

• 37464-90-7 5,8-dimethoxy-2-tetralone 
• 64831-69-2 (2S,3S)-3-(2-Hydroxy-ethylamino)-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ol 
• 58851-65-3 (2S,3S)-3-Isopropylamino-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-ol 
• 75251-98-8 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene 
• 33628-85-2 (+/-)-2-acetyl-2-hydroxy-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene 
• 612096-62-5 2-benzenesulfonyl-5,8-dimethoxy-1,2-dihydro-naphthalene 
• 28693-86-9 1,4-diallyl-2,5-bis-allyloxy-benzene 
• 137833-39-7 2,3,5,6-Tetraallyl-benzene-1,4-diol 
• 612096-61-4 2-benzenesulfonyl-3-chloro-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalene 
• 10075-62-4 1,4-dimethoxynaphthalene 
• 58851-64-2 6,7-epoxy-5,6,7,8-tetrahydro-1,4-dimethoxynaphthalene 
• 55077-80-0 1,4-Dimethoxy-5,6-dihydronaphthalene 
• 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

Studies in the cycloproparene series: Oxygen-containing 1H-cyclopropa[b]naphthalenes and their methylidene derivatives

3,6-Dimethoxy-1H-cyclopropa[b]naphthalene 4 is available from 1,4-benzoquinone in four steps in 27-28% overall yield. The diether 4 provides a range of methylidene derivatives 15a-e by way of the disilyl compound 14, and is efficiently demethylated by cerium(IV) ammonium nitrate to provide 1H-cyclopropa[b]naphthalene-3,6-dione 16 (85%) whose crystal structure is reported. Quinone 16 is the first stable cyclopropaquinone but it resists conversion into a 1-C exocyclic olefin. The chemistry of the compounds is described, their spectral data are discussed, and the cyclic voltammetry of 16 is provided.

Construction of a tube-like molecule via sequential cyclopropylidene dimerisation and intramolecular [π2s+π2s] cycloaddition reactions

The syn-cyclopropylidene dimer 5, obtained by reaction of compound 4 with methyllithium, is readily elaborated to the bis-p-benzoquinone 7 which undergoes intramolecular [π2s+π2s] cycloaddition to give the tube-like molecule 8.

Synthesis and luminescence of soluble meso-unsubstituted tetrabenzo- and tetranaphtho[2,3]porphyrins

Syntheses of soluble tetrabenzoporphyrins (TBP) and tetranaphtho[2,3] porphyrins (TNP), with multiple substituents in the conjugated aromatic rings but bearing no substituents in the meso-positions, is reported. Both types of porphyrins were obtained by direct aromatization of precursor porphyrins, annealed with either cyclohexene or dihydronaphthalene fragments. TBPs and TNPs possess powerful absorption bands in the near-infrared (λ = 610-710 nm, ε = 100,000-300,000 M-1 cm-1) and exhibit strong luminescence. Free bases and Zn complexes fluoresce with quantum yields of up to 50%, whereas Pd and Pt complexes phosphoresce in solutions at ambient temperatures. Remarkably, the phosphorescence quantum yields of Pd and Pt TBPs reach as high as 20-50%, which places them among the brightest near-infrared phosphors known to date.

Synthesis of anthracyclinone precursor: 5,12-dihydroxy-1,3,4- trihydronaphthacene-2,6,11-quinone

Two practical and efficient approaches for preparing large quantities of 5,12-dihydroxy-1,3,4-trihydronaphthacene-2,6,11-quinone 9 are described. Both synthetic approaches involve a simple route with a fewer number of steps and utilize readily available and inexpensive starting materials. Large-scale production of this precursor may prove to be useful for further research involving the synthesis of antineoplastic anthracyclines and development of their analogs with increased activity and decreased toxicity.

Combined Multiple Claisen Rearrangement and Ring-closing Metathesis as a Route to Naphthalene, Anthracene, and Anthracycline Ring Systems

A new route involving double Claisen rearrangement of a suitable 1,4-diallyloxyarene system followed by ring-closing metathesis of the resulting diene has been developed for the synthesis of various benzannulated cyclohexenes. An important demonstration of this methodology is the construction of the tetracyclic quinophenolic ring system of the clinically important anthracyclines.

Methylidenecycloproparenes: Novel Compounds with Fascinating Properties

Proton abstraction from the methylene position of a cycloproparene provides the corresponding C1 anion that can be intercepted by a carbonyl-containing compound to provide a wide range of novel methylidenecycloproparenes. The physical and chemical aspects of this comparatively new class of surprisingly stable, strained compounds have been explored. The present account provides a perspective on these developments from the initial experiments in the Utah laboratories.

1H-Cyclopropanaphthalene-3,6-dione

Cerium ammonium nitrate demethylation and oxidation of 3,6-dimethoxy-1H-cyclopropanaphthalene 6 provides 1H-cyclopropanaphthalene-3,6-dione 8 as the first stable cyclopropaquinone.

THE SYNTHESIS AND IDENTIFICATION OF ISOMERIC PRODUCTS OF ENZYMATIC O-DEMETHYLATION OF THE SYMPATHOMIMETIC TETRAMINOL - trans-3-(2-HYDROXYETHYLAMINO)-5,8-DIMETHOXY-1,2,3,4-TETRAHYDRO-2-NAPHTHOL

The structure of the positional isomers of mono-O-demethylated metabolites (V and VI) of Tetraminol - trans-3-(2-hydroxyethylamino)-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol (XIX) - and the pairs of related derivatives was determined.

P-aminophenols, derivatives thereof and method of use

p-Aminophenols are provided having the structure STR1 wherein m is 0, 1 or 2; n is 0, 1, 2 or 3; R1 and R2 may be the same or different and are H, hydroxy or alkoxy; R3 is H, lower alkyl, alkanoyl or aroyl and R4 is H, lower alkyl or alkanoyl, and including acid-addition salts thereof. These compounds are useful as inhibitors of leukotriene production and as such are useful as antiallergy, anti-inflammatory and anti-psoriatic agents.