127660-84-8

Upstream product

• 67886-70-8 2-cyano-6-methoxynaphthalene 
• 1589-82-8 phenylmagnesium bromide 
• 93-04-9 2-Methoxynaphthalene 
• 103-80-0 phenylacetyl chloride 
• 3900-45-6 6-methoxy-2-acetylnaphthalene 
• 108-90-7 chlorobenzene 
• 3453-33-6 6-methoxynaphthalene-2-carbaldehyde 
• 6921-34-2 benzylmagnesium chloride 
• 158689-13-5 7-methoxy-1-naphthyl phenyl ketone 
• 5672-94-6 1-acetyl-2-methoxynaphthalene 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 4747-15-3 1-(2-methoxyvinyl)benzene 

Downstream Products

• 860196-52-7 6-bromo-2-(6-methoxy-[2]naphthyl)-3-phenyl-quinoline 

Relevant academic research and scientific papers

Engineering the Active Site of an (S)-Selective Amine Transaminase for Acceptance of Doubly Bulky Primary Amines

A protein engineering approach for expanding the substrate scope of the (S)-selective Chromobacterium violaceum amine transaminase is presented. Amino acid residues in the small binding pocket of the active site were targeted in order to increase the pocket size for acceptance of primary amines bearing two bulky groups. A highly sensitive fluorescence assay was then used to evaluate the generated enzyme variants for their activity towards propyl- and benzyl-substituted screening substrates. The best variant, L59A/F88A, was successfully applied in the kinetic resolution of 1,2-diphenylethylamine using different conditions and substrate loadings. The variant L59A/F88A generated enantiomerically pure (R)-1,2-diphenylethylamine with ee>99% under all tested conditions. The variant also holds great promise for synthesis of hydrophobic compounds as it shows optimum activity when 20-30% (v/v) DMSO is applied as cosolvent. The variant L59A/F88A provides a great addition to the available catalyst toolbox for synthesis of chiral amines, as it is the first published (S)-selective amine transaminase showing activity towards benzyl-substituted primary amines. (Figure presented.).

General and mild Ni0-catalyzed α-arylation of ketones using aryl chlorides

A general methodology for the α-arylation of ketones using a nickel catalyst has been developed. The new well-defined [Ni(IPr)(cin)Cl] (1c) pre-catalyst showed great efficiency for this transformation, allowing the coupling of a wide range of ketones, including acetophenone derivatives, with various functionalised aryl chlorides. This cinnamyl-based Ni-N-heterocyclic carbene (NHC) complex has demonstrated a different behaviour to previously reported NHC-Ni catalysts. Preliminary mechanistic studies suggest a Ni0/NiII catalytic cycle to be at play.

Environmentally benign contemporary Friedel-Crafts acylation of 1-halo-2-methoxynaphthalenes and its related compounds under conventional and nonconventional conditions

Environmentally benign simple and practical method has been developed in cationic micellar media for the selective acylations of 1-halo-2- methoxynaphthalenes, 2-methoxynaphthalene, anisole, 2-methoxypyridine, and 2-methoxypyrimidine. Developed protocols

Heck reactions of α- or β-substituted enol ethers with aryl bromides catalysed by a tetraphosphane/palladium complex - Direct access to acetophenone or 1-arylpropanone derivatives

cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphanylmethyl)cyclopentane/ [PdCl(C3H5)]2 efficiently catalyses the Heck reaction of α- and β-substituted enol ethers with aryl bromides. The arylation of 1-phenyl-1-(trimethylsilyloxy) ethylene led directly to the 2-aryl-1-phenylethanones. Similar reaction rates were observed with electron-rich, electron-deficient or sterically congested aryl bromides. Heck reaction with benzyl isopropenyl ether gave a mixture of isomers. However, this mixture gave selectively the 1-arylpropanones after hydrolysis. Employing β-methoxystyrene, 3-ethoxyacrylonitrile or methyl 3-methoxyacrylate, the regioselective α-arylation of these enol ethers was observed in all cases, but mixtures of (Z) and (E) isomers were generally obtained, which in many cases yielded a single ketone product after acid treatment. The stereoselectivity of this reaction depends on steric and electronic factors, and better stereoselectivities in favour of (Z) isomers were observed with electron-rich or sterically congested aryl bromides. Higher yields were obtained for this reaction with electron-rich or sterically congested aryl bromides than with electron-poor aryl bromides. These observations suggest that the rate-limiting step of the catalytic cycle is not the oxidative addition of the aryl bromide to the palladium complex with these substituted enol ethers. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Heck reactions of 2-substituted enol ethers with aryl bromides catalysed by a tetraphosphine/palladium complex

cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/ [PdCl(C3H5)]2 efficiently catalyses the Heck reaction of β-substituted enol ethers with aryl bromides. Employing β-methoxystyrene, 3-ethoxyacrylonitrile or methyl 3-methoxyacrylate, the regioselective α-arylation of these enol ethers was observed in all cases, and mixtures of Z and E isomers were generally obtained, which in many cases yielded a single ketone product after acid treatment. The stereoselectivity of this reaction depends on steric and electronic factors, and better stereoselectivities in favour of Z isomers were observed with electron-rich or sterically congested aryl bromides. Better yields were obtained for this reaction with electron-rich or sterically congested aryl bromides than with electron-poor aryl bromides. This observation suggests that with these β-substituted enol ethers the rate-limiting step of the catalytic cycle is not the oxidative addition of the aryl bromide to the palladium complex.

Acylation of 2-Methoxynaphthalene with Acyl Clorides in the Presence of a Catalytic Amount of Lewis Acids

The regiochemistry of the reaction of 2-methoxynaphthalene 1 with benzoyl chloride 2a using a catalytic amount of Lewis acid is strongly influenced by the identity of the acid catalyst employed as well as by the reaction temperature.By using InCl3, FeCl3, SnCl4 or ZnCl2 and heating at 160 deg C, 2-benzoyl-6-methoxynaphthalene 4a is selectively produced along with 1-benzoyl-7-methoxynaphthalene 5a, while in the case of AlCl3, SbCl5 or TiCl4, 1-benzoyl-2-methoxynaphthalene 3a is the major product. 2-Acyl-6-methoxynaphthalenes 4b-e can be selectively obtained using InCl3 and the corresponding acyl chlorides 2b-e in place of 2a.In the presence of a stoichiometric amount of InCl3, the reaction of 1 with 2a also gives 4a as the predominant product along with 5a even at 50 deg C.This reaction appears to involve isomerisation of 3a to 4a and 5a.

Mild and Reversible Friedel-Crafts Acylation: Synthesis of 6-Acyl-2-methoxynaphthalenes

A new practical method for large scale preparation of 2-acyl-6-methoxynaphthalenes 3 is reported.The selectivity toward 3 is due to reversibility of the Friedel-Crafts acylation and to the termodynamic stability of 3.