163837-32-9

Usage

Uses

Used in Recreational Drug Use:
(S)-PCP is used as a recreational drug for its hallucinogenic and dissociative effects. However, its use can result in unpredictable and dangerous outcomes, including hallucinations, delusions, and disorientation.

Upstream product

• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 474654-19-8 (S)-(-)-N-[(4-chlorophenyl)(phenyl)methyl]formamide 
• 134-85-0 4-chlorobenzophenone 
• 28022-43-7 p-chlorobenzhydrylamine 
• 1309582-68-0 N,N'-sulfonyl bis-[(4-chlorophenyl)(phenyl)methanamine] 
• 104-88-1 4-chlorobenzaldehyde 
• 934-56-5 trimethyl(phenyl)stannane 
• 336105-23-8 (R)-(-)-N-[(1E)-(4-chlorophenyl)methylene]-2-methyl-2-propanesulfinamide 
• 186249-76-3 (R,E)-2-methyl-N-(phenylmethylene)-2-propanesulfinamide 
• 100-52-7 benzaldehyde 
• 357417-22-2 N-(4-chlorobenzylidene)-4-methylbenzenesulfonamide 
• 260997-38-4 N-(4-chloro-benz-(E)-ylidene)-4-nitro-benzenesulfonamide 
• 3262-89-3 triphenylboroxine 
• 796966-17-1 (S)-N-((4-chlorophenyl)(phenyl)methyl)-4-methylbenzenesulfonamide 

Downstream Products

• 292066-77-4 [(S)-(4-Chloro-phenyl)-phenyl-methyl]-(2,2-dimethoxy-ethyl)-amine 
• 163837-58-9 1-[(S)-(4-Chloro-phenyl)-phenyl-methyl]-4-(toluene-4-sulfonyl)-piperazine 
• 1246755-20-3 (S)-(+)-N-[(4-chlorophenyl)(phenyl)methyl]pivalamide 
• 41839-60-5 p-chlorobenzophenone imine 
• 134-85-0 4-chlorobenzophenone 
• 1198162-46-7 (-)-1-[(4-chloro-phenyl)-phenyl-methyl]-4-(4-methoxy-benzyl)piperazine 
• 292066-78-5 N-[(4-chloro-phenyl)-phenyl-methyl]-N-(2,2-dimethoxy-ethyl)-formamide 
• 246870-46-2 (S)-(-)-cetirizine ethyl ester 
• 439858-21-6 1-[(S)-(4-chlorophenyl)(phenyl)methyl]piperazine 
• 130018-87-0 (+)-Cetirizine dihydrochloride 

Relevant academic research and scientific papers

C2-symmetric bicyclo[2.2.2]octadienes as chiral ligands: Their high performance in rhodium-catalyzed asymmetric arylation of N-tosylarylimines

Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95-99% ee) was realized by use of a new C2-symmetric diene ligand, (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (Ph-bod*), for the rhodium-catalyzed asymmetric arylati

Isopropylamine as Amine Donor in Transaminase-Catalyzed Reactions: Better Acceptance through Reaction and Enzyme Engineering

Amine transaminases (ATA) have now become frequently used biocatalysts in chemo-enzymatic syntheses including industrial applications. They catalyze the transfer of an amine group from a donor to an acceptor leading to an amine product with high enantiopurity. Hence, they represent an environmentally benign alternative for waste intensive chemical amine synthesis. Isopropylamine (IPA) is probably one of the most favored amine donors since it is cheap and achiral, but nevertheless there is no consistency in literature concerning reaction conditions when IPA is best to be used. At the same time there is still a poor understanding which structural properties in ATA are responsible for IPA acceptance. Herein, we demonstrate, on the basis of the 3FCR enzyme scaffold, a substantial improvement in catalytic activity towards IPA as the amine donor. The asymmetric synthesis of industrial relevant amines was used as model reaction. A systematic investigation of the pH-value as well as concentration effects using common benchmark substrates and several ATA indicates the necessity of a substrate- and ATA-dependent reaction engineering.

Simultaneous engineering of an enzyme's entrance tunnel and active site: The case of monoamine oxidase MAO-N

A new directed evolution approach is presented to enhance the activity of an enzyme and to manipulate stereoselectivity by focusing iterative saturation mutagenesis (ISM) simultaneously on residues lining the entrance tunnel and the binding pocket. This combined mutagenesis strategy was applied successfully to the monoamine oxidase from Aspergillus Niger (MAO-N) in the reaction of sterically demanding substrates which are of interest in the synthesis of chiral pharmaceuticals based on the benzo-piperidine scaffold. Reversal of enantioselectivity of Turner-type deracemization was achieved in the synthesis of (S)-1,2,3,4-tetrahydro-1-methyl-isoquinoline, (S)-1,2,3,4-tetrahydro-1-ethylisoquinoline and (S)-1,2,3,4-tetrahydro-1-isopropylisoquinoline. Extensive molecular dynamics simulations indicate that the altered catalytic profile is due to increased hydrophobicity of the entrance tunnel acting in concert with the altered shape of the binding pocket.

Identification of (S)-selective transaminases for the asymmetric synthesis of bulky chiral amines

The use of transaminases to access pharmaceutically relevant chiral amines is an attractive alternative to transition-metal-catalysed asymmetric chemical synthesis. However, one major challenge is their limited substrate scope. Here we report the creation of highly active and stereoselective transaminases starting from fold class I. The transaminases were developed by extensive protein engineering followed by optimization of the identified motif. The resulting enzymes exhibited up to 8,900-fold higher activity than the starting scaffold and are highly stereoselective (up to >99.9% enantiomeric excess) in the asymmetric synthesis of a set of chiral amines bearing bulky substituents. These enzymes should therefore be suitable for use in the synthesis of a wide array of potential intermediates for pharmaceuticals. We also show that the motif can be engineered into other protein scaffolds with sequence identities as low as 70%, and as such should have a broad impact in the field of biocatalytic synthesis and enzyme engineering.

Bis-sulfamyl imines: Potent substrates for asymmetric additions of arylboroxines under rhodium catalysis

Bis-sulfamyl imines are shown to be potentially ideal substrates for rhodium-catalysed asymmetric additions of arylboron nucleophiles as they show: (i) near perfect enantioselectivities (11 examples, 98-99+% ee), (ii) good to excellent diastereoselectivities (10-32:1 rac:meso), and (iii) high functional group tolerance in removal of the low molecular weight protecting group via mild heating in aqueous pyridine.

Highly enantioselective synthesis of (diarylmethyl)amines by rhodium-catalyzed arylation of N-nosylimines using a chiral bicyclo[3.3.0]diene ligand

A highly efficient asymmetric arylation of N-nosylimines with arylboronic acids catalyzed by a rhodium-diene complex is described. A wide range of enantiopure (98-99% ee) N-(diarylmethyl)nosylamides, as well as (3S)-2-(4-nosyl)-3-phenylisoindolin-1-one, were obtained in high yields (83-99%) under very mild conditions. Georg Thieme Verlag Stuttgart New York.

Stereospecific Suzuki-Miyaura coupling of chiral α-(Acylamino) benzylboronic esters with inversion of configuration

The first invertive B-alkyl Suzuki-Miyaura coupling has been achieved. The coupling of enantioenriched α-(acylamino)benzylboronic esters with aryl bromides and chlorides took place efficiently in toluene at 80 °C in the presence of Pd(dba)2 (5 mol %), XPhos (10 mol %), K 2CO3 (3 equiv), and H2O (2 equiv). The reaction proceeded with inversion of configuration to give diarylmethanamine derivatives in high yields with high conservation of enantiomeric excesses.

C2-symmetric bicyclo[3.3.1]nonadiene as a chiral ligand for rhodium-catalyzed asymmetric arylation of N-(4-nitrobenzenesulfonyl)arylimines

(Chemical Equation Presented) Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95-99percent ee) was realized by use of a new C 2-symmetric diene ligand, (1R,5R)-2,6-diphenylbicyclo[3.3.1]nona-2,6- diene (Ph-bnd*), for th

Asymmetric synthesis of diarylmethyl amines by rhodium-catalyzed asymmetric addition of aryl titanium reagents to imines

A rational tuning of the arene sulfonamide moiety (by introducing isopropyl groups onto the phenyl ring) brought about high enantioselectivity in the asymmetric synthesis of diarylmethyl amines by the title reaction (see scheme). Ar1 = 4-CF3C6H4, 4-ClC 6H4, 4-FC6H4, 3-MeOC 6H4, 4-MeOC6H4, 2-MeC 6H4, 1-naphthyl, Ph; Ar2 = Ph, 4-FC 6H4, 3-MeOC6H4, 4-MeOC 6H4.

Effective tuning of the arene and alkanesulfinamides for highly enantioselective synthesis of (S)-4-chlorophenylphenylmethylamine, a key intermediate for antihistamic (S)-cetirizine

High diastereoselectivity (>94%) has been achieved in the phenylMgBr addition process to chlorophenyl aldimine derived from the new and sterically hindered triisopropylbenzene sulfinamide (TIPBSA) in the synthesis of a key intermediate of (S)-Cetirizine. Surprisingly, under the same reaction conditions, toluenesulfinamide derived chlorophenyl aldimine provided only 10% ee.