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Usage

Uses

Used in Pharmaceutical Research:
5,8-DiMethoxy-2-acetyl-3,4-dihydronaphthalene is used as a research compound for its potential applications in the development of new drugs. Its unique structure and properties make it a promising candidate for further exploration and synthesis of bioactive compounds.
Used in Organic Synthesis:
In the field of organic synthesis, 5,8-DiMethoxy-2-acetyl-3,4-dihydronaphthalene is used as a precursor in the synthesis of various pharmaceuticals and bioactive compounds. Its versatility as a chemical intermediate allows for the creation of a wide range of molecules with potential therapeutic applications.
Used in Medicinal Chemistry:
5,8-DiMethoxy-2-acetyl-3,4-dihydronaphthalene is utilized in medicinal chemistry as a key intermediate for the synthesis of drug candidates. Its structure and properties contribute to the development of innovative therapeutic agents with improved efficacy and safety profiles.
Used in Drug Discovery:
As a component of drug discovery efforts, 5,8-DiMethoxy-2-acetyl-3,4-dihydronaphthalene plays a crucial role in identifying and optimizing new chemical entities with potential therapeutic benefits. Its unique characteristics make it an essential tool in the search for novel treatments and pharmaceutical advancements.

Upstream product

• 69031-42-1 2-Ethynyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene 
• 76437-10-0 (+/-)-2-(1-hydroxy-ethyl)-5,8-dimethoxy-3,4-dihydronaphthalene 
• 82407-71-4 2-(5,8-Dimethoxy-3,4-dihydro-naphthalen-2-yl)-2-methyl-[1,3]dithiolane 
• 88928-58-9 5.8-diacetoxy-3-acetyl-1,2-dihydronaphthalene 
• 77-78-1 dimethyl sulfate 
• 37464-90-7 5,8-dimethoxy-2-tetralone 
• 79060-58-5 5,8-dimethoxy-3,4-dihydro-2-naphthaldehyde 
• 1083-11-0 4-(2,5-dimethoxyphenyl)butyric acid 
• 82407-70-3 5,8-Dimethoxy-2-(2-methyl-[1,3]dithiolan-2-yl)-3,4-dihydro-2H-naphthalen-1-one 
• 71366-26-2 2-acetyl-5,8-dimethoxytetralone 
• 1015-55-0 5,8-dimethoxytetralone 
• 3090-45-7 5,8-dihydro-1,4-naphthalenediol 
• 10075-62-4 1,4-dimethoxynaphthalene 
• 35043-92-6 cis-5,8,9,10-tetrahydronaphtho-1,4-quinone 

Downstream Products

• 76527-48-5 (+/-)-2-acetyl-6-(2-methoxycarbonylbenzoyl)-5,8-dimethoxy-1,2,3,4-tetrahydro-2ol 
• 76527-49-6 (+/-)-2-acetyl-6-(2-carboxybenzoyl)-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol 
• 33628-85-2 (+/-)-2-acetyl-2-hydroxy-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene 
• 41098-96-8 (R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

SIMPLE SYNTHESIS OF 2-ACETYL-5,8-DIMETHOXY-3,4-DIHYDRONAPHTHALENE, A KEY INTERMEDIATE FOR THE SYNTHESIS OF OPTICALLY ACTIVE ANTHRACYCLIONES

2-Acetyl-5,8-dimethoxy-3,4-dihydronaphthalene is synthesised easily, starting from 2-acetyl-5,8-dimethoxytetralone.

Simple synthesis of 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene: A key intermediate for the synthesis of 4-demethoxydaunomycinone

2-Acetyl-5,8-dimethoxy-3,4-dihydronaphthalene is prepared by using a 1,3-dipolar cycloaddition of nitrile oxide to the corresponding dihydronaphthalene.

Efficient enantioselective synthesis of (R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, the key intermediate in the synthesis of anthracycline antibiotics

A simple, efficient, enantioselective synthesis of (R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, the key intermediate in the synthesis of anthracycline antibiotics, is described. The synthetic procedure starts with the Sharpless asymmetric dihydroxylation of 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene: the diol obtained is regioselectively transformed into the corresponding chloroacetate which is dehalogenated and saponified to give the desired title compound in four steps with satisfactory yield (52%). No separation step is necessary at any point of the synthetic process. An efficient procedure for the synthesis of the starting enone and the stereoselectivity of the methanolysis of the intermediate chloroacetate are also reported.

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 HIGH YIELD SYNTHESIS OF (+/-)-5,8-DIMETHOXY-2-α-HYDROXYETHYL-3,4-DIHYDRONAPHTHALENE, A KEY INTERMEDIATE IN ANTRACYCLINONE SYNTHESIS

The dimethoxytetralol (2) gives on Vilsmeier reaction the dihydronaphthaldehyde (3) (yield, 92percent), which on Grignard reaction with MeMgI affords the title compound (6) (yield, ca. 100percent), the reactions constituting a high yield synthesis of this important antracyclinone intermediate.

4-DEMETHOXY-9-DEOXY-9-METHYLDAUNORUBICIN

The synthesis of the α-daunosaminyl derivatives of (+)- and (-)-4-demethoxy-9-deoxy-9-methyldaunomycinone is reported.The new compounds are inactive in the P 388 lymphocytic leukemia test.

A NOVEL SYYNTHESIS OF (+/-)-2-ACETYL-5,8-DIMETHOXY-1,2,3,4-TETRAHYDRO-2-NAPHTHOL, A KEY INTERMEDIATE FOR THE SYNTHESIS OF ANTHRACYCLINONES

The title compound ((+/-)-3) was prepared from readily available 5,8-dimethoxy-3,4-dihydro-2-naphthoic acid(4), according to the novel synthetic route visuelized in Scheme I.