66646-88-6

Usage

Uses

Used in Pharmaceutical Industry:
METHYL ((PHENYLMETHYLIDENE)AMINO ACETAT&) is used as a potential candidate for the development of new drugs for the treatment of various medical conditions due to its antioxidant and anti-inflammatory properties.
Used in Medical Research:
METHYL ((PHENYLMETHYLIDENE)AMINO ACETAT&) is used in research for its potential role in promoting muscle growth and improving exercise performance, with further studies needed to fully understand its potential uses and effects.

InChI:InChI=1/C10H11NO2/c1-13-10(12)8-11-7-9-5-3-2-4-6-9/h2-7H,8H2,1H3/b11-7+

Upstream product

• 5680-79-5 glycine ethyl ester hydrochloride 
• 100-52-7 benzaldehyde 
• 616-34-2 methoxycarbonylmethylamine 
• 6000-43-7 2-aminoethanoic acid hydrochloride 
• 922-68-9 Methyl glyoxylate 
• 100-46-9 benzylamine 

Downstream Products

• 70471-01-1 3-(3,4-Dimethoxy-phenyl)-2-{[1-phenyl-meth-(Z)-ylidene]-amino}-propionic acid methyl ester 
• 66646-70-6 2-amino-4-benzyloxy-3-hydroxy-butyric acid methyl ester 
• 111396-08-8 3-(4-Chloro-phenyl)-5-oxo-5-phenyl-2-{[1-phenyl-meth-(Z)-ylidene]-amino}-pentanoic acid methyl ester 
• 111836-48-7 4-(2-Phenyl-[1,3]dioxolan-2-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-butyric acid methyl ester 
• 113273-72-6 (2S,3R,4S,5R)-4-(4-Methyl-benzoyl)-3,5-diphenyl-pyrrolidine-2-carboxylic acid methyl ester 
• 131570-80-4 dimethyl t-3-dimethoxymethyl c-5-phenyl-r-2,c-4-pyrrolidinedicarboxylate 
• 111836-49-8 5-(2-Phenyl-[1,3]dioxolan-2-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-pentanoic acid methyl ester 
• 126616-58-8 2',3'-isopropylidene-5'-(6-(methoxycarbonyl)-6-(benzylideneamino)-1-phenyl-1-hexyn-3-yl)-5'-deoxyadenosine 
• 113273-67-9 (2SR,3RS,4SR,5RS)-2,4-dimethyl 3,5-diphenylpyrrolidine-2,4-dicarboxylate 
• 113273-69-1 (2R,4R,5S)-4-Acetyl-5-phenyl-pyrrolidine-2-carboxylic acid methyl ester 
• 104769-87-1 methyl benzylidene hex-5-enylglycine 
• 119111-69-2 1-{[1-Phenyl-meth-(E)-ylidene]-amino}-cyclopropanecarboxylic acid methyl ester 
• 113273-68-0 (2R,4R,5R)-4-Methyl-5-phenyl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester 
• 113273-71-5 (2S,3R,4S,5R)-4-Acetyl-3,5-diphenyl-pyrrolidine-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

A powerful azomethine ylide route mediated by TiO2photocatalysis for the preparation of polysubstituted imidazolidines

Lewis- and Br?nsted-acid catalyzed 1,3-dipolar cycloaddition between azomethine ylides and unsaturated compounds is an important strategy to construct five-membered N-heterocycles. However, such a catalytic route usually demands substrates with an electron-withdrawing group (EWG) to facilitate the reactivity. Herein, we report a TiO2photocatalysis strategy that can conveniently prepare five-membered N-heterocyclic imidazolidines from a common imine (N-benzylidenebenzylamine) and alcohols along the route of 1,3-dipolaron azomethine ylide but without pre-installed EWG substituents on the substrates. Our EPR results uncovered the previously unknown mutual interdependence between an azomethine ylide and TiO2photo-induced hvb+/ecb?pair. This transformation exhibited a broad scope with 21 successful examples and could be scaled up to the gram level.

Sequential [6+2], [2+2], and [3+2] annulations for rapid assembly of multiple fragments

Assembly of four components through sequential [6+2], [2+2], and [3+2] annulations on an azulenone manifold allows for five-step access to a natural product-inspired scaffold with exquisite control of the ten consecutive stereocenters. X-ray analysis was used to define the spatial arrangement of the three fragments and functional groups on this rigid scaffold. The Royal Society of Chemistry.

Highly diastereoselective multicomponent synthesis of unsymmetrical imidazolines.

We report here a highly diastereoselective multicomponent synthesis of imidazolines. These low molecular weight scaffolds contain a four-point diversity applicable to alkyl, aryl, acyl, and hetereocyclic substitutions. [structure: see text]

Novel asymmetric synthesis of spiroindene-1,3dione-pyrrolidines via CoII/amino acids complex catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides and 2-arylidenindane-1,3-diones

Cobalt II(L-phenylalanine)2 was used effectively for the first time in a catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with 2-arylidenindane-1,3-diones, affording a series of novel spiropyrrolidine derivatives with good to

Copper/GanPhos-Catalyzed 1,3-Dipolar Cycloaddition of Azo?-methine Ylides: An Efficient Access to Chiral Pyrrolidine Spirocycles

A highly efficient copper/GanPhos-catalyzed 1,3-dipolar cyclo?-addition?-of azomethine ylides is reported. This viable transformation provides a series of optically active spiro[dihydronaphthalene-2,3′-pyrrolidine]s, bearing one spiro quaternary and three tertiary stereogenic centers, in good yields and with high ee values. This protocol features high diastereo- A nd enantioselectivity, broad substrate scope and mild reaction conditions.

Silver-Mediated [3 + 2] Cycloaddition of Azomethine Ylides with Trifluoroacetimidoyl Chlorides for the Synthesis of 5-(Trifluoromethyl)imidazoles

A silver-mediated [3 + 2] cycloaddition of azomethine ylides with trifluoroacetimidoyl chlorides for the rapid assembly of 5-(trifluoromethyl)imidazoles has been developed. Notable features of the reaction include readily accessible reagents, a broad substrate scope, and high efficiency. The protocol can be successfully applied to construct the analogue of the specific allosteric modulator of GABAA receptors. The silver species could be recycled by a simple operation.

Boron Dipyrromethene (BODIPY) as Electron-Withdrawing Group in Asymmetric Copper-Catalyzed [3+2] Cycloadditions for the Synthesis of Pyrrolidine-Based Biological Sensors

In this work, we describe the use of Boron Dipyrromethene (BODIPY) as electron-withdrawing group for activation of double bonds in asymmetric copper-catalyzed [3+2] cycloaddition reactions with azomethine ylides. The reactions take place under smooth conditions and with high enantiomeric excess for a large number of different substituents, pointing out the high activation of the alkene by using a boron dipyrromethene as electron-withdrawing group. Experimental, theoretical studies and comparison with other common electron-withdrawing groups in asymmetric copper-catalyzed [3+2] cycloadditions show the reasons of the different reactivity of the boron dipyrromethene derivatives, which can be exploited as a useful activating group in asymmetric catalysis. Additional experiments show that the so obtained pyrrolidines can be employed as biocompatible biosensors, which can be located in the endosomal compartments and do not present toxicity in three cell lines. (Figure presented.).

Copper(i)/Ganphos catalysis: enantioselective synthesis of diverse spirooxindoles using iminoesters and alkyl substituted methyleneindolinones

A copper-catalyzed asymmetric 1,3-dipolar cycloaddition of glycine iminoesters with alkyl substituted 3-methylene-2-oxindoles is described. By usingde novodesign of P-stereogenic phosphines as ligands, spiro[pyrrolidin-3,3'-oxindole]s are generated in good to excellent yields with high asymmetric induction. A further reduced catalyst loading of 0.1 mol% is sufficient to achieve a satisfactory enantioselectivity of 90% ee. The DFT calculations suggest the second Michael addition of the 1,3-dipole to be the rate- andenantio-determining step. A key feature of this 1,3-dipolar cycloaddition is the wide substrate applicability, even with alkyl aldehyde-derived azomethine ylide; thus it has streamlined a highly enantioselective access to a new class of antiproliferative agents, MDM2-p53.

Tunable Synthesis of α-Amino Boronic Esters from Available Aldehydes and Amines through Sequential One-Pot Dehydration and Copper-Catalyzed Borylacylation

Copper-catalyzed multicomponent borylacylation of imines with acid chlorides and bis(pinacolato)diboron was developed for the preparation of synthetically useful and pharmacologically relevant α-amino boronic acid derivatives. Starting from a range of acid chlorides and imines with aryl, heteroaryl, and alkyl substituents, most of these ligand-free reactions proceeded smoothly at room temperature in moderate to good yields. Furthermore, a facile and convenient one-pot, multistep access to the direct synthesis of α-amino boronic acid derivatives from available aldehydes and amines was also developed.

Silver/palladium relay catalyzed 1,3-dipole annulation/allylation reactions to access fully substituted allyl imidazolidines

A silver/palladium relay catalyzed 1,3-dipole annulation/allylation reaction of iminoesters and Baylis-Hillman acetates for the construction of fully substituted allyl imidazolidines is reported. The reaction of both iminoesters and Baylis-Hillman acetate