67106-36-9

Usage

Uses

Used in Fragrance and Flavoring Industry:
Ethanone, 1-(3,4-dihydro-1-naphthalenyl)is used as a key ingredient in the fragrance and flavoring industry for its distinctive floral scent. It contributes to the creation of various perfumes, colognes, and food flavorings, enhancing the sensory experience of consumers.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 1-tetralone serves as an intermediate in the synthesis of various organic compounds and drugs. Its chemical properties make it a valuable component in the development of new medications, contributing to advancements in healthcare and medicine.
Used in Chemical Synthesis:
Ethanone, 1-(3,4-dihydro-1-naphthalenyl)is utilized as a versatile intermediate in chemical synthesis across different industries. Its unique structure allows for the production of a wide range of organic compounds, facilitating innovation and diversification in chemical manufacturing.

Upstream product

• 941-98-0 1'-naphthacetophenone 
• 24764-66-7 1-acetyl-4-methoxynaphthalene 
• 77103-90-3 1-(1-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)ethanone 
• 54470-97-2 3,4-dihydro-[1]naphthoyl chloride 
• 75-16-1 methylmagnesium bromide 
• 544-97-8 dimethyl zinc(II) 
• 506-82-1 dimethylcadmium 
• 7677-24-9 trimethylsilyl cyanide 
• 917-54-4 methyllithium 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 96945-09-4 1-(3,4-dihydronaphthalen-1-yl)-ethanol 
• 3333-23-1 3,4-dihydronaphthalene-1-carboxylic acid 
• 123994-49-0 3,4-dihydro-1-naphthyl triflate 
• 82720-23-8 2-ethynyl-1,2,3,4-tetrahydronaphthalen-2-ol 

Downstream Products

• 872809-12-6 2-methyl-4-oxo-1,4,4a,9,10,10a-hexahydro-phenanthrene-1-carboxylic acid ethyl ester 
• 781-19-1 4-methyl-3,4,4a,5,6,10b-hexahydrobenzoquinolin-1(2H)-one 
• 83669-12-9 13-Oxo-2,6-dimethyl-2,3,4,5,6,6a,7,8-octahydro-4,12b-methano-1H-naptho<2,1-b><1,5>diazocine 
• 92697-20-6 Acetat d. Enolform v. 1-Acetyl-3,4-dihydro-naphthalin 
• 883090-95-7 1-(α-trimethylsiloxyvinyl)-3,4-dihydronaphthalene 

Relevant academic research and scientific papers

Mild conversion of propargylic alcohols to α,β-unsaturated enones in ionic liquids (ILs); A new 'metal free' life for the Rupe rearrangement

A mild and selective transition metal free protocol for the conversion of propargylic alcohols to cyclic and acyclic α,β-unsaturated enones via the Rupe rearrangement is reported. The method utilizes the Br?nsted acidic ionic liquid [BMIM-SO3H][OTf] as catalyst and [BMIM][PF 6] as solvent and offers the potential for recycling and reuse of the IL solvent. The feasibility to synthesize bicyclic fused cyclopentenone derivatives via a Rupe → Aldol → Nazarov sequence utilizing this protocol has also been demonstrated.

Mild and efficient nickel-catalyzed heck reactions with electron-rich olefins

A new efficient protocol for the nickel-catalyzed Heck reaction of aryl triflates with vinyl ethers is presented. Mild reaction conditions that equal those of the corresponding palladium-catalyzed Heck reaction are applied, representing a practical and more sustainable alternative to the conventional regioselective arylation of vinyl ethers. A catalytic system comprised of Ni(COD)2 and 1,1″-bis(diphenylphosphino)ferrocene (DPPF) in combination with the tertiary amine Cy2NMe proved effective in the olefination of a wide range of aryl triflates. Both electron-deficient and electron-rich arenes proved compatible, and the corresponding aryl methyl ketone could be secured after hydrolysis in yields approaching quantitative. Good functional group tolerance was observed matching the characteristics of the analogous Pd-catalyzed Heck reaction. The high levels of catalytic activity were explained by the intermediacy of a cationic nickel(II) complex potentially responsible for the successive β-hydride elimination and base promoted catalyst regeneration. Although these elementary reactions are normally considered challenging, DFT calculations suggested this pathway to be favorable under the applied reaction conditions.

INHIBITORS OF CYSTEINE PROTEASES AND METHODS OF USE THEREOF

The present invention relates to semicarbazone or thiosemicarbazone inhibitors of cysteine proteases and methods of using such compounds to prevent and treat protozoan infections such as trypanosomiasis, malaria and leishmaniasis. The compounds also find use in inhibiting cysteine proteases associated with carcinogenesis, including cathepsins B and L.

Design, synthesis, and biochemical evaluation of novel cruzain inhibitors with potential application in the treatment of Chagas' disease

A series of compounds bearing tetrahydronaphthalene, benzophenone, propiophenone, and related rigid molecular skeletons functionalized with thiosemicarbazone or unsaturated carbonyl moieties were prepared by chemical synthesis and evaluated for their ability to inhibit the enzyme cruzain. As potential treatment agents for Chagas' disease, three compounds from the group demonstrate potent inhibition of cruzain with IC50 values of 17, 24, and 80 nM, respectively.

Azasteroids. synthesis by Diels-Alder reaction between maleimides, citraconimide, and triazolindiones and 1-(1-trialkylsiloxyvinyl)-3,4- dihydronaphthalene derivatives

18-Nor-16-azaestrane derivatives with 8β, 13β, and 14β orientation were isolated from Diels-Alder reactions between maleimides or citraconimide and 1-(1-siloxyvinyl)naphthalene derivatives. (8RS)-13,14,16- Triazaestrane derivatives were synthesized from 1,2,4-triazolin-3,5-diones. The parent 11-oxo derivatives were obtained by desilylation, and they were transformed into 11-hydroxyimino derivatives. 3-Hydroxy derivatives, finally were synthesized by cleavage of the 3-methoxy group with BBr3. During these transformations the stereochemistry of the steroidal skeleton was not changed. The stereochemistry of these "unnatural" steroids was elucidated by spectroscopic methods, and compared with results from calculations, and with the configuration of natural estrane derivatives. Finally, an improved method for the synthesis of the starting material, 6-methoxy-1-[(1-trialkylsiloxy)-vinyl]-3,4-dihydronaphthalene was developed. Springer-Verlag 2005.

Calcium metal in liquid ammonia for selective reduction of organic compounds

Selective reduction of functional groups by use of dissolving calcium metal was performed, and the results are in comparison with those by lithium and sodium metals. Reduction with 2.0-2.2 equiv of calcium led chromone (1) to 4-chromanone (2, 75% yield), coumarin (4) to dihydrocoumarin (5, 76% yield) and 3-(2-hydroxyphenyl)-1-propanol (6, 6% yield), α-tetralone (7) to 1,2,3,4-tetrahydro-1-naphthol (8, 81% yield), and β-methoxystyrene (12) to methyl phenethyl ether (13, 85% yield). Performance of reductions on the same substrates by use of 4.0 equiv of lithium or sodium metal gave over-reduced products. Reduction of indole-3-carboxaldehyde (15) to 3-indolemethanol (16), 1-acetylnaphthalene (17) to 1-acetyl-3,4-dihydronaphthalene (18), and trans-4-phenyl-3-buten-2-one (19) to 4-phenyl-2-butanone (20) were accomplished by use of calcium, lithium, and sodium metals, among which calcium gave the highest yields (80-90%). Being a milder reducing agent than lithium and sodium, calcium metal in liquid ammonia offered a better selectivity.

SELECTIVE BIRCH REDUCTION OF 1-ACYL-4,6-DIMETHOXYNAPHTHALENES

By the action of sodium and alcohol in liquid ammonia on 1 compound 3 was obtained in a preparatively useful manner.The same reagent caused demethoxylation and ring reduction of 1-acetyl-4-methoxynaphthalene and a similar transformation of 2 to 7.It was shown on the basis of the experimental data how the course of these reactions is influenced by the structural features of 1-acylnaphthalene derivative and by the applied experimental procedure.

Studies on Simplified Ergoline Derivatives. A General Six-Step Synthesis of Phenyl-Substituted 4-Methyl-3,4,4a,5,6,10b-hexahydrobenzoquinolin-1-(2H)-one Analogs (1)

This communication outlines the development of a novel, general synthetic route to substituted α-tetralones 5, their subsequent conversion to the α,β-unsaturated ketones 11, and an improved, one-step transformation of 11 to the tricyclic title compounds 1.Thus, substituted derivatives of 1 can be prepared in six steps from simple benzaldehydes, or, in three steps from more readily available α-tetralones.

Studies in Metal-Ammonia Reduction. Part 3. Reduction and Reductive Methylation of Some Acylnaphthalenes with Metal-Ammonia Solutions

Birch reduction and reductive methylation of 1- and 2-acetylnaphthalenes have been examined.It has been found that, while 1-acetylnaphthalene is reduced to the 3,4-dihydro-compound, the 2-acetylnaphthalene gives the corresponding 1,2,3,4-tetrahydro-compound.However, anhydrous ferric chloride has been found to limit the reduction and reductive methylation to the dihydro-stage with 2-acetylnaphthalene.The factors influencing the mechanism of the reduction process have been discussed.Some of the intermediate compounds are useful substrates in synthesis.