186296-21-9

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-p-chloro-N-acetyl-1-methylbenzylamine is used as a reagent in chemical synthesis for the production of chiral pharmaceuticals. Its chirality plays a crucial role in the development of enantiomerically pure drugs, which can have different biological activities and reduce potential side effects.
Used in Agrochemical Industry:
PCAMB is also used as a reagent in the synthesis of chiral agrochemicals, contributing to the development of more effective and selective pesticides and other agricultural products.
Used in Organic Chemistry:
(R)-(+)-p-chloro-N-acetyl-1-methylbenzylamine serves as a building block in organic chemistry, where its unique structure and properties make it a valuable tool for creating complex and diverse molecules. Its use in various synthetic pathways allows for the exploration of new chemical reactions and the synthesis of novel compounds with potential applications in various fields.

Upstream product

• 108-24-7 acetic anhydride 
• 1167414-87-0 C₈H₁₀ClN*ClH 
• 208118-80-3 1-(4-chlorophenyl)ethenylacetamide 
• 108-05-4 vinyl acetate 
• 35588-60-4 p-chloro-(R,S)-1-phenylethylamine 
• 141-78-6 ethyl acetate 
• 108-22-5 Isopropenyl acetate 
• 1121583-62-7 isopropyl 2-propoxyacetate 
• 4187-56-8 (S)-1-(p-chlorophenyl)ethylamine 
• 1420472-32-7 (E)-1-(4-chlorophenyl)ethanone O-acetyl oxime 
• 99-91-2 para-chloroacetophenone 
• 1956-39-4 4-chloroacetophenone oxime 
• 1956-39-4 (E)-1-(4-chlorophenyl)ethanone oxime 
• 937371-83-0 (E)-1-(4-chlorophenyl)ethanone O-benzyl oxime 

Relevant academic research and scientific papers

Monophosphite ligands derived from carbohydrates and H8-BINOL: Highly enantioselective Rh-catalyzed asymmetric hydrogenations

A series of monophosphite ligands derived from carbohydrates and H 8-BINOL have been synthesized. Excellent enantioselectivities (over 99% ee) were obtained when these ligands were applied in the Rh-catalyzed asymmetric hydrogenation of dimethy

Enantioselective hydrogenation of enamides catalyzed by chiral rhodium-monodentate phosphite complexes

Chiral monophosphites derived from BINOL are cheap and efficient ligands in the Rh-catalyzed hydrogenation of N-acyl enamides, providing amines with high degrees of enantioselectivity (up to 97.0% ee).

Asymmetric enamide hydrogenation using planar-chiral cyrhetrenes

The catalytic asymmetric hydrogenation of α-arylenamides using catalysts prepared in situ from [Rh(cod)2]BF4 and cyrhetrenyldiphosphines was effective with a range of enamides. The corresponding acetamides were obtained with up to 93

Catechol-based phosphoramidites: A new class of chiral ligands for rhodium-catalyzed asymmetric hydrogenations

The synthesis and application of a new class of catechol-based phosphoramidites is described. Ees up to 99% were obtained in the rhodium-catalyzed asymmetric hydrogenation of dehydroamino acids and enamides.

Biocatalytic, Intermolecular C?H Bond Functionalization for the Synthesis of Enantioenriched Amides

Directed evolution of heme proteins has opened access to new-to-nature enzymatic activity that can be harnessed to tackle synthetic challenges. Among these, reactions resulting from active site iron-nitrenoid intermediates present a powerful strategy to forge C?N bonds with high site- and stereoselectivity. Here we report a biocatalytic, intermolecular benzylic C?H amidation reaction operating at mild and scalable conditions. With hydroxamate esters as nitrene precursors, feedstock aromatic compounds can be converted to chiral amides with excellent enantioselectivity (up to >99 % ee) and high yields (up to 87 %). Kinetic and computational analysis of the enzymatic reaction reveals rate-determining nitrenoid formation followed by stepwise hydrogen atom transfer-mediated C?H functionalization.

Diaza-Crown Ether-Bridged Chiral Diphosphoramidite Ligands: Synthesis and Applications in Asymmetric Catalysis

A small library of diaza-crown ether-bridged chiral diphosphoramidite ligands was prepared. In the rhodium-catalyzed asymmetric hydrogenation and hydroformylation reactions, these ligands exhibited distinct properties in catalytic activity and/or enantioselectivity. Hydrogenated products with opposite absolute configurations could be obtained in high yields with excellent ee values by utilizing (S,S)-L1 and (S,S)-L3, respectively. Meanwhile, the addition of alkali metal cations caused variations in catalytic outcomes, showing the supramolecular tunability of these Rh/diphosphoramidite catalytic systems.

Development of robust heterogeneous chiral rhodium catalysts utilizing acid?base and electrostatic interactions for efficient continuous-flow asymmetric hydrogenations

Heterogeneous chiral Rh catalysts based on acid?base and electrostatic interactions have been developed. The robust catalysts demonstrate high activity and selectivity in the continuous-flow asymmetric hydrogenation of a wide variety of enamides and dehyd

New chiral ferrocene/indole-based diphosphine ligands for Rh-catalyzed asymmetric hydrogenation of functionalized olefins

Convenient synthesis of a new family of chiral ferrocene/indole-based diphosphine ligands, (Rc,Rp)-IndoFerroPhos (L), from (Sc,Rp)-PPFA and 2-(diphenylphosphino)indole has been described. These new ligands exhibited high efficiency in the Rh-catalyzed asymmetric hydrogenation of functionalized olefins including α-dehydroamino acid esters, α-enamides and dimethyl itaconate, in which up to >99% yield and 98% ee were achieved.

The enzymatic resolution of 1-(4-chlorophenyl)ethylamine by Novozym 435 to prepare a novel triazolopyrimidine herbicide

The kinetic resolution of (R,S)-1-(4-chlorophenyl)ethylamine was accomplished using a commercial lipase from Candida antarctica (Novozym 435). The performance of this lipase was investigated for the enantioselective amidation of (R,S)-1-(4-chlorophenyl)ethylamine, leaving the target product (S)-1-(4-chlorophenyl)ethylamine in its unreacted form. The effects of various types of solvents and an acyl donor, the molar ratio of the substrate to the acyl donor, and the reaction temperature were studied. The optimum reaction conditions were found to result in amidation with methyl 2-tetrahydrofuroate at 40°C in methyl tert-butyl ether, with a substrate/acyl donor molar ratio of 1:2.4. The conversion rate of (R,S)-1-(4-chlorophenyl)ethylamine was 52%, with an enantiomeric excess of 99% towards the unreacted substrate in a reaction time of 22?hours. Finally, using optically pure (S)-1-(4-chlorophenyl)ethylamine as the raw material, the chemical synthesis of (S)-N-(1-(4-chlorphenyl)ethyl)-2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)acetamide, a novel triazolopyrimidine herbicide, was achieved, and the total yield and purity were 83.5% and 95.3%, respectively.

Optimization of 2-alkoxyacetates as acylating agent for enzymatic kinetic resolution of chiral amines

In this study, the activity of acetic acid esters modified with electron withdrawing 2-alkoxy-groups was investigated as acylating agent in kinetic resolution (KR) of racemic amines. A homologous series of the isopropyl esters of four 2-alkoxyacetic acids (2-methoxy-, 2-ethoxy-, 2-propoxy- and 2-butoxyacetic acids) were prepared and investigated for enantiomer selective N-acylation, catalyzed by lipase B from Candida antarctica, under batch and continuous-flow conditions. In the first set of experiments, isopropyl 2-propoxyacetate showed the highest effectivity with all of the four racemic amines [(±)-1-phenylethylamine, (±)-4-phenylbutan-2-amine, (±)-heptan-2-amine and (±)-1-methoxypropane-2-amine] in the set enabling excellent conversions (≥46%) and enantiomeric excess values (ee ≥ 99%) with each amines in continuous-flow mode KRs under the optimized reaction conditions. In a second set of experiments, KRs of five additional amines – being substituted derivatives of (±)-1-phenylethylamine – further demonstrated the usefulness of isopropyl 2-propoxyacetate – being the best acylating agent in the first set of KRs – in KRs leading to (R)-N-propoxyacetamides with high ee values (≥99.8%).