124049-62-3

Upstream product

• 41526-55-0 2-phenylmethylene-7-methoxy-1-tetralone 
• 6836-19-7 7-Methoxy-1-tetralone 
• 100-39-0 benzyl bromide 
• 108-18-9 diisopropylamine 
• 32820-10-3 7-methoxy-1,2,3,4-tetrahydro-1-naphthol 
• 100-51-6 benzyl alcohol 
• 89496-35-5 2-benzyl-4-(4-methoxyphenyl)-4-oxo-butyric acid 

Downstream Products

• 1255327-15-1 2-benzyl-7-methoxy-1-trimethylsilyloxytetral-1-ene 
• 1314305-88-8 2-benzyl-7-methoxy-1-(trifluoroacetoxy)tetral-1-ene 
• 360767-01-7 (2-benzyl-1-hydroxy-7-methoxy-1,2-dihydro-naphthalen-1-yl)-acetonitrile 
• 360767-03-9 2-benzyl-7-methoxy-1-naphthylacetonitrile 
• 360766-97-8 1-hydroxy-2-benzyl-7-methoxy-1,2,3,4-tetrahydro-1-naphthylacetonitrile 

Relevant academic research and scientific papers

Nickel-Catalyzed Selective Synthesis of α-Alkylated Ketones via Dehydrogenative Cross-Coupling of Primary and Secondary Alcohols

Herein, we describe an isolable, air-stable, homogeneous, nickel catalyst that performs dehydrogenative cross-coupling reaction between secondary and primary alcohols to result α-alkylated ketone products selectively. The sequence of steps involve in this one-pot reaction is dehydrogenation of both alcohols, condensation between the ketone and the aldehyde, and hydrogenation of the in situ-generated α,β-unsaturated ketone. Preliminary mechanistic investigation hints a radical mechanism following borrowing hydrogen reaction. (Figure presented.).

Iron-Catalyzed Ligand Free α-Alkylation of Methylene Ketones and β-Alkylation of Secondary Alcohols Using Primary Alcohols

Herein, we demonstrate a general and broadly applicable catalytic cross coupling of methylene ketones and secondary alcohols with a series of primary alcohols to disubstituted branched ketones. A simple and nonprecious Fe2(CO)9 catalyst enables one-pot oxidations of both primary and secondary alcohols to a range of branched gem-bis(alkyl) ketones. A number of bond activations and formations selectively occurred in one pot to provide the ketone products. Coupling reactions can be performed in gram scale and successfully applied in the synthesis of an Alzehimer's drug. Alkylation of a steroid hormone can be achieved. A single catalyst enables sequential one-pot double alkylation to bis-hetero aryl ketones using two different alcohols. Preliminary mechanistic studies using an IR probe, deuterium labeling, and kinetic experiments established the participation of a borrowing-hydrogen process using Fe catalyst, and the reaction produces H2 and H2O as byproducts.

Nickel-Catalyzed Hydrogen-Borrowing Strategy for α-Alkylation of Ketones with Alcohols: A New Route to Branched gem-Bis(alkyl) Ketones

The α-alkylation of ketones using an earth-abundant and nonprecious NiBr2/L1 system is reported. This nickel-catalyzed reaction could be performed in gram scale and successfully applied in the synthesis of donepezil (Alzheimer's drug) and functionalization of steroid hormones and fatty acid derivatives. Synthesis of N-heterocycles, methylation of ketones, and one-pot double alkylation to bis-hetero aryl ketones using two different alcohols with a single catalyst broadens the scope of the catalytic protocol. Preliminary mechanistic studies using defined Ni-H species and deuterium-labeling experiments established the participation of the borrowing-hydrogen strategy.

Mn(ii)-catalysed alkylation of methylene ketones with alcohols: Direct access to functionalised branched products

Herein an operationally simple alkylation of methylene ketones with primary alcohols is reported. Use of an inexpensive and earth abundant Mn/1,10-phenanthroline system enables direct access to a series of functionalised branched ketones including one-pot sequential double alkylation and Alzheimer's drug donepezil. Preliminary mechanistic investigation, determination of the rate and order of reactions and deuterium labeling experiments support the participation of the hydrogen-borrowing strategy for the ketone alkylation.

Organocatalyzed enantioselective protonation of silyl enol ethers: Scope, limitations, and application to the preparation of enantioenriched homoisoflavones

In the present work, enantioselective protonation of silyl enol ethers is reported by means of a variety of chiral nitrogen bases as catalysts, mainly derived from cinchona alkaloids, in the presence of various protic nucleophiles as proton source. A detailed study of the most relevant reaction parameters is disclosed allowing high enantioselectivities of up to 92% ee with excellent yields to be achieved under mild and eco-friendly conditions. The synthetic utility of this organocatalytic protonation was demonstrated during the preparation of two homoisoflavones 4a and 4b, isolated from Chlorophytum Inornatum and Scilla Nervosa, which were obtained with 81% and 78% ee, respectively.

Synthesis of naphthalenic melatonin receptor ligands

A highly efficient and versatile synthetic approach to the synthesis of naphthalenic analogs of melatonin, compound 7, and its 2-alkyl substituted analog 8 is described. This approach features the novel synthesis of substituted 1-naphthyl acetonitrile 12 and 19 by nucleophilic addition of LiCH2CN to substituted 1-tetralone, followed by aromatization via a 2-step reaction sequence, dehydrogenation with DDQ and TsOH catalyzed dehydration.

Substituted tetralins, chromans and related compounds in the treatment of asthma, arthritis and related diseases

Substituted tetralins, chromans and related compounds which, by inhibiting 5-lipoxygenase enzyme and/or blocking leukotriene receptors, are useful in the prevention or treatment of asthma, arthritis, psoriasis, ulcers, myocardial infarction and related disease states in mammals, pharmaceutical compositions thereof, a method of treatment therewith, and to intermediates useful in the synthesis thereof.