80467-87-4

Upstream product

• 27829-46-5 N,N-diethylcinnamide 
• 60-29-7 diethyl ether 
• 33609-25-5 3-bromo-1,1-diphenylpropan-2-one 
• 109-89-7 diethylamine 
• 27829-46-5 (E)-N,N-diethyl-3-phenylacrylamide 
• 71-43-2 benzene 
• 621-82-9 Cinnamic acid 
• 102-92-1 cinnamoyl chloride 
• 637-44-5 phenylpropyolic acid 
• 85241-00-5 N,N-diethyl-3-phenyl-2-propynamide 
• 102-92-1 Cinnamoyl chloride 
• 140-10-3 (E)-3-phenylacrylic acid 

Relevant academic research and scientific papers

Synthesis method of N,N-dialkyl diphenyl propionamide

The invention discloses a synthesis method of N,N-dialkyl diphenyl propionamide. The method is characterized by accelerating coupling reaction of diphenylketone and N,N-dialkyl acetamide under the action of p-toluenesulfonic acid in the absence of solvent

One-pot tandem hydrophenylation and ionic hydrogenation of 3-phenylpropynoic acid derivatives under superelectrophilic activation

The reactions of esters and amides of 3-phenylpropynoic acid with strong Lewis acids AlX3 (X = Cl, Br) or conjugate Br?nsted-Lewis superacids HX-AlX3 (X = Cl, Br) in benzene and cyclohexane at room temperature afforded 3,3-diphenylpropanoic acid derivatives in up to 94% yield. This tandem reaction of the acetylene bond proceeded by hydrophenylation followed by ionic hydrogenation.

Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals

Cinnamides ArCHCHCONRR′ in reactions with arenes Ar′H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1-2 h give CC bond hydroarylation products ArAr′CHCH2CONRR′ in yields of 63-98%. Reduction (LiAlH4/Et2O) of carbonyl group in the latter results in the formation of 3,3-diarylpropylamines ArAr′CHCH2CH2NRR′, valuable drugs. The reaction intermediates, superelectrophilic dications ArC+H-CH2C(OH+)NRR′, have been characterized by DFT calculations in terms of global electrophilicity index, natural charges, and atomic orbitals contributions.

Superelectrophilic activation of polyfunctional organic compounds using zeolites and other solid acids

Zeolites and other available solid acids have been successfully applied to initiate reactions, which were earlier recognised to involve superelectrophilic intermediates and thus required excess of superacids to be carried out.

Friedel-Crafts alkylation of benzene with α,β-unsaturated amides

A variety of α,β-unsaturated amides (RHC=CH 2CONR′2, R=H, Me, Ar; R′=H or Et) readily condense with benzene at room temperature in the presence of an excess of aluminum chloride to give the corresponding 3-phenylpropionamides in excellent yields. This simple, one-pot procedure proved to be efficient and very clean. The mechanism of these and related reactions is discussed and the participation of superelectrophilic dicationic intermediates is suggested.

Superacidic activation of α,β-unsaturated amides and their electrophilic reactions

The electrophilic reactivity of α,β-unsaturated amides towards weak nucleophiles such as arenes and cyclohexane, initiated either with triflic acid (CF3SO3H) or with excess AlCl3, has been studied. The amides generally condense readily with aromatics in the presence of AlCl3 to give 3-arylpropionamides and related compounds in excellent yields, while some amides also undergo selective ionic hydrogenation with cyclohexane to give saturated amides. The proposed mechanism of these reactions involves dicationic intermediates (superelectrophiles). The direct observation of a dicationic species (by low-temperature NMR) is reported. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.