6315-96-4

Usage

Uses

Used in Organic Synthesis:
1-(2-naphthyl)propan-1-one is used as an intermediate in the synthesis of organic compounds and pharmaceuticals, leveraging its aromatic ketone structure to facilitate the creation of a range of products.
Used in Perfumery:
In the fragrance industry, 1-(2-naphthyl)propan-1-one is used as a key ingredient in perfumes, capitalizing on its strong, sweet, and floral scent to enhance the olfactory profiles of various fragrances.
Used in Flavoring Agents:
1-(2-naphthyl)propan-1-one is also employed in the production of flavoring agents, where its aromatic properties contribute to the taste and smell of different food products and beverages.
Used in Chemical Research:
1-(2-naphthyl)propan-1-one serves as a valuable compound in chemical research, particularly in studies involving the properties and reactions of aromatic ketones and their derivatives.
It is important to handle and store 1-(2-naphthyl)propan-1-one with care due to its potential health and safety hazards, which include irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C13H12O/c1-2-13(14)12-8-7-10-5-3-4-6-11(10)9-12/h3-9H,2H2,1H3

Upstream product

• 613-46-7 2-naphthalenecarbonitrile 
• 925-90-6 ethylmagnesium bromide 
• 91-20-3 naphthalene 
• 79-03-8 propionyl chloride 
• 123-62-6 propionic acid anhydride 
• 93-08-3 methyl 2-naphthyl ketone 
• 592-02-9 diethylcadmium 
• 2243-83-6 2-naphthaloyl chloride 
• 74-88-4 methyl iodide 
• 580-13-2 2-bromonaphthalene 
• 3857-83-8 2-naphthyl triflate 
• 1067-52-3 tributyltin methoxide 
• 3249-50-1 1-propenyl acetate 
• 113443-62-2 N-methoxy-N-methylnaphthalene-2-carboxamide 

Downstream Products

• 861038-47-3 (3-methyl-2-[2]naphthyl-[4]quinolyl)-phenyl-amine 
• 93-09-4 naphthalene-2-carboxylate 
• 154667-96-6 α(RS)-ethyl-2-naphthalenemethylamine 
• 57221-66-6 (E)-1-Naphthalen-2-yl-3-(2-nitro-phenyl)-propenone 
• 3042-57-7 2-(pentan-3-yl)naphthalene 
• 6241-75-4 1-(2-naphthyl)-1-phenyl-1-propene 

Relevant academic research and scientific papers

Photoredox/nickel-catalyzed hydroacylation of ethylene with aromatic acids

We report a general, practical and scalable hydroacylation reaction of ethylene with aromatic carboxylic acids with the synergistic combination of nickel and photoredox catalysis. Under ambient temperature and pressure, feedstock chemicals such as ethylene can be converted into high-value-added aromatic ketones in moderate to good yields (up to 92%) with reaction time of 2-6 hours.

Nickel-Mediated Enantiospecific Silylation via Benzylic C-OMe Bond Cleavage

Benzylic stereocenters are found in bioactive and drug molecules, as enantiopure benzylic alcohols have been used to build such a stereogenic center, but are limited to the construction of a C-C bond. Silylation of alkyl alcohols has the potential to build bioactive molecules and building blocks; however, the development of such a process is challenging and unknown. Herein, we describe an unprecedented AgF-assisted nickel catalysis in the enantiospecific silylation of benzylic ethers.

SUBSTITUTED DIHYDROPYRAZOLO PYRAZINE CARBOXAMIDE DERIVATIVES

The invention relates to substituted dihydropyrazolo pyrazine carboxamide derivatives and to processes for their preparation, and also to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular cardiovascular disorders, preferably thrombotic or thromboembolic disorders, and diabetes, and also urogenital and ophthalmic disorders.

Isomerization of Allylic Alcohols to Ketones Catalyzed by Well-Defined Iron PNP Pincer Catalysts

[Fe(PNP)(CO)HCl] (PNP=di-(2-diisopropylphosphanyl-ethyl)amine), activated in situ with KOtBu, is a highly active catalyst for the isomerization of allylic alcohols to ketones without an external hydrogen supply. High reaction rates were obtained at 80 °C, but the catalyst is also sufficiently active at room temperature with most substrates. The reaction follows a self-hydrogen-borrowing mechanism, as verified by DFT calculations. An alternative isomerization through alkene insertion and β-hydride elimination could be excluded on the basis of a much higher barrier. In alcoholic solvents, the ketone product is further reduced to the saturated alcohol.

Ligand-Controlled Chemoselective C(acyl)-O Bond vs C(aryl)-C Bond Activation of Aromatic Esters in Nickel Catalyzed C(sp2)-C(sp3) Cross-Couplings

A ligand-controlled and site-selective nickel catalyzed Suzuki-Miyaura cross-coupling reaction with aromatic esters and alkyl organoboron reagents as coupling partners was developed. This methodology provides a facile route for C(sp2)-C(sp3) bond formation in a straightforward fashion by successful suppression of the undesired β-hydride elimination process. By simply switching the phosphorus ligand, the ester substrates are converted into the alkylated arenes and ketone products, respectively. The utility of this newly developed protocol was demonstrated by its wide substrate scope, broad functional group tolerance and application in the synthesis of key intermediates for the synthesis of bioactive compounds. DFT studies on the oxidative addition step helped rationalizing this intriguing reaction chemoselectivity: whereas nickel complexes with bidentate ligands favor the C(aryl)-C bond cleavage in the oxidative addition step leading to the alkylated product via a decarbonylative process, nickel complexes with monodentate phosphorus ligands favor activation of the C(acyl)-O bond, which later generates the ketone product.

Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents

The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.

Highly chemoselective and versatile method for direct conversion of carboxylic acids to ketones utilizing zinc Ate complexes

Various carboxylic acids were directly transformed into the corresponding ketones by utilizing organozinc ate complexes, which provide high chemoselectivity without any overreaction to the undesired tertiary carbinol, owing to formation of a stable tetrahedral zincioketal intermediate. This method offers good overall atom/step/pot economy and operational simplicity. No need to overreact: Various carboxylic acids were directly transformed to the corresponding ketones by utilizing organozinc ate complexes, which provide high chemoselectivity without any overreaction to undesired tertiary carbinol, owing to formation of a stable tetrahedral zincioketal intermediate. This method offers good overall atom/step/pot economy and operational simplicity.

Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the SRN1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

Direct conversion of allyl arenes to aryl ethylketones via a TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes

A TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes was developed. This methodology provides a new efficient and simple route for conversion of a range of allyl arenes directly into aryl ethylketones in good yields with high chemoselectivity.

Ruthenium-catalyzed tandem-isomerization/asymmetric transfer hydrogenation of allylic alcohols

A one-pot procedure for the direct conversion of racemic allylic alcohols to enantiomerically enriched saturated alcohols is presented. The tandem-isomerization/ asymmetric transfer hydrogenation process is efficiently catalyzed by [{Ru(p-cymene)Cl2}2] in combination with the a-amino acid hydroxyamide ligand 1, and performed under mild conditions in a mixture of ethanol and THF. The saturated alcohol products are isolated in good to excellent chemical yields and in enantiomeric excess up to 93%.