7474-19-3

Usage

InChI:InChI=1/C15H15NO/c16-15(17)11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H,11H2,(H2,16,17)

Upstream product

• 2286-54-6 3,3-diphenyl-propionitrile 
• 591-50-4 iodobenzene 
• 621-79-4 cinnamamide 
• 890-35-7 3,3-Diphenylpropionamidoxime 
• 5661-55-2 4-phenylazetidin-2-one 
• 71-43-2 benzene 
• 1073-67-2 4-vinylbenzyl chloride 
• 174876-28-9 C₁₈H₁₄ 
• 21161-19-3 (+/-)-4-(p-tolyl)-2-azetidinone 
• 21161-20-6 1-tert-butoxycarbonyl-2-(4'-chloro)phenylazetidine 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 18166-64-8 4-chlorocinnamide 
• 18254-00-7 (E)-3-(4-Methylphenyl)-2-propenamide 
• 130973-06-7 p-bromocinnamamide 

Downstream Products

• 2286-54-6 3,3-diphenyl-propionitrile 
• 149553-65-1 2-(2,2-diphenylethyl)-3-isopropylidene-5,5-dimethylpyrrolidine 
• 149553-59-3 2-(2,2-diphenylethyl)-3-isopropylidene-5,5-dimethyl-1-pyrroline 
• 46969-60-2 2-(2,2-diphenyl-ethyl)-thiazole 
• 66192-30-1 N-hydroxymethyl-3,3-diphenyl-propionamide 
• 3963-62-0 2,2-Diphenylethylamine 
• 5586-73-2 3-diphenylpropyl amine 

Relevant academic research and scientific papers

Palladium-catalyzed regiodivergent hydroaminocarbonylation of alkenes to primary amides with ammonium chloride

Palladium-catalyzed hydroaminocarbonylation of alkenes for the synthesis of primary amides has long been an elusive aim. Here, we report an efficient catalytic system which enables inexpensive NH4Cl to be utilized as a practical alternative to gaseous ammonia for the palladium-catalyzed alkene-hydroaminocarbonylation reaction. Through appropriate choice of the palladium precursors and ligands, either branched or linear primary amides can be obtained in good yields with good to excellent regioselectivities. Primary mechanistic studies were conducted and disclosed that electrophilic acylpalladium species were capable of capturing the NH2-moiety from ammonium salts to form amides in the presence of CO with NMP as a base.

Primary fatty acid amide preparation method

The present invention provides a primary fatty acid amide preparation method. According to the present invention, under the action of a single auxiliary agent phosphine-containing transition metal catalyst or a combined auxiliary agent comprising a phosphine-free transition metal catalyst and a phosphine-containing ligand, terminally substituted olefin or cyclo-olefin, carbon monoxide and an ammonium salt are subjected to a hydrogen carboamidation reaction so as to prepare the primary fatty acid amide compound in one step; the raw material and the catalyst of the reaction are inexpensive and easy to obtain, and the synthesis process is simple, such that the synthesis cost is substantially reduced; the preparation method has characteristics of mild reaction condition and high yield, and issuitable for industrial production; and the raw material and the catalyst of the reaction are clean, non-toxic and low environment pollution.

Pd(II)/bipyridine catalyzed conjugate addition of arylboronic acids to α,β-unsaturated amides

The Pd(II)/bipyridine-catalyzed conjugate addition of arylboronic acid to α,β-unsaturated amides was developed and optimized, and the reaction was proceeded smoothly in air. A series of arylboronic acid and α,β-unsaturated amide substrates were surveyed, and modest to excellent yields were given.

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.

The acid-mediated ring opening reactions of α-aryl-lactams

4-Aryl-azetidin-2-ones (β-lactams) undergo ring opening with triflic acid to give cinnamamides which, in benzene, react further to give 3-aryl-3-phenyl-propionamides. Prolonged reaction times in benzene give 3,3-diphenyl-propionamide via an aryl/phenyl ex

Facile synthesis of γ-alkenylbutenolides from Baylis-Hillman adducts: Consecutive in-mediated Barbier allylation, PCC oxidation, isomerization, and Zn-mediated Barbier allylation

Alkenylbutenolides were synthesized regioselectively in good to moderate yields from Baylis-Hillman adducts via a consecutive indium-mediated Barbier type reaction between Baylis-Hillman bromide and aldehyde, PCC oxidation of the homoallylic alcohol, doub

Dicationic intermediates involving protonated amides: Dual modes of reactivity including the acylation of arenes

Matrix presented. In the Bronsted superacid CF3SO 3H (triflic acid), amides are able to form reactive, dicationic electrophiles. It is shown that these dicationic intermediates participate in two distinctly different types of electrophilic reactions. The protonated amide increases the reactivity of an adjacent electrophilic group, and the protonated amide group itself shows enhanced reactivity arising from an adjacent cationic charge. In the latter case, several types of amides are even capable of reacting with benzene by Friedel-Crafts acylation.

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.

Histaprodifens: Synthesis, pharmacological in vitro evaluation, and molecular modeling of a new class of highly active and selective histamine H1-receptor agonists

A new class of histamine analogues characterized by a 3,3-diphenylpropyl substituent at the 2-position of the imidazole nucleus has been prepared outgoing from 4,4-diphenylbutyronitrile (4b) via cyclization of the corresponding methyl imidate 5b with 2-oxo-4-phthalimido-1-butyl acetate or 2-oxo-1,4-butandiol in liquid ammonia, followed by standard reactions. The title compounds displayed partial agonism on contractile H1 receptors of the guinea-pig ileum and endothelium-denuded aorta, respectively, except 10 (histaprodifen; 2-[2-(3,3-diphenylpropyl)1H-imidazol-4-yl]ethanamine) which was a full agonist in the ileum assay. While 10 was equipotent with histamine (1), methylhistaprodifen (13) and dimethylhistaprodifen (14) exceeded the functional potency of 1 by a factor of 3-5 (13) and 2-3 (14). Compounds 10 and 13-17 relaxed precontracted rat aortic rings (intact endothelium) with relative potencies of 3.3- up to 28-fold (compared with 1), displaying partial agonism as well. Agonist effects were sensitive to blockade by the selective H1-receptor antagonist mepyramine (pA2 ? 9 (guinea-pig) and pA2 ? 8 (rat aorta)). The affinity of 10 and 13-17 for guinea-pig H1 receptors increased 20- to 100-fold compared with 1. Two lower homologues of 10 were weak partial H1-receptor agonists while two higher homologues of 10 were silent antagonists endowed with micromolar affinity for rat and guinea-pig H1 receptors. In functional selectivity experiments, 10, 13, and 14 did not stimulate H2, H3, and several other neurotransmitter receptors. They displayed only low to moderate affinity for these sites (pA2 1 receptor were studied using molecular dynamics simulations. Remarkable differences were found between the binding modes of 10, 13, and 14 and that of 1. The imidazole ring of 10, 13, and 14 was placed 'upside down' compared with 1, making the interaction of the N(π)-atom with Tyr431 possible. This new orientation was mainly caused by the space filling substitution at the 2-position of the imidazole ring and influenced the location of the protonated N(α)-atom which was positioned more between TM III and TM VI. This orientation can explain both the increased relative potency and the maximum effect of 10, 13, and 14 compared with 1. Compound 13 (methylhistaprodifen; N(α)-methyl-2-[2-(3,3-diphenylpropyl)-1H-imidazol-4- yl]ethanamine) is the most potent histamine H1-receptor agonist reported so far in the literature and may become a valuable tool for the study of physiological and pathophysiological H1-receptor-mediated effects.