5650-45-3

Usage

Chemical class

Ketone derivative

Structural features

A phenyl group and a morpholine ring attached to the second carbon atom of the propanone backbone

Uses

Versatile building block in organic synthesis, intermediate in the synthesis of pharmaceuticals and biologically active compounds

Neurotoxic effects

Can be metabolized into a compound that selectively destroys dopaminergic neurons in the brain, potential role in parkinsonism.

Upstream product

• 110-91-8 morpholine 
• 70-11-1 α-bromoacetophenone 
• 66217-95-6 β-Morpholino-β-methyl styrene 
• 27313-32-2 2,2-dichloropropanal 
• 98-80-6 phenylboronic acid 
• 93-55-0 1-phenyl-propan-1-one 
• 6084-15-7 2-iodo-1-phenylpropan-1-one 
• 120972-13-6 N-iodomorpholine-hydrogen iodide 
• 93-54-9 1-Phenyl-1-propanol 
• 108-86-1 bromobenzene 
• 637-50-3 1-phenylpropene 
• 21120-36-5 1-fluoroethyl phenyl ketone 
• 3626-56-0 2-morpholinopropanenitrile 
• 591-51-5 phenyllithium 

Downstream Products

• 93764-54-6 2,6-dimethyl-3,5-diphenylpyrazine 
• 54600-85-0 2,5-dimethyl-3,6-diphenylpyrazine 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 115045-14-2 (1R,2S)-2-morpholino-1-phenylpropan-1-ol 
• 13739-49-6 2,5⁽⁴⁾-dimethyl-4⁽⁵⁾-phenylimidazole 

Relevant academic research and scientific papers

A five coordination Cu(II) cluster-based MOF and its application in the synthesis of pharmaceuticals: Via sp3 C-H/N-H oxidative coupling

Herein, a copper metal-organic framework, termed as VNU-18, containing penta-coordinated sites was successfully synthesized and fully characterized. This material was demonstrated to be an efficient heterogeneous catalyst for the oxidative C-H activation via N-H bonds. The optimized conditions are applicable for the synthesis of pharmaceuticals constructed by α-amino carbonyl skeletons.

Enantioselective and Diastereoselective Construction of Chiral Amino Alcohols by Iridium-f-Amphox-Catalyzed Asymmetric Hydrogenation via Dynamic Kinetic Resolution

The iridium-f-amphox-catalyzed asymmetric hydrogenation of racemic α-amino β-unfunctionalized ketones proceeds via a DKR (dynamic kinetic resolution) process for the construction of various chiral N,N-disubstituted α-amino β-unfunctionalized alcohols in quantitative yields with excellent enantioselectivities and diastereoselectivities (all products >99% ee and >99:1 dr, TON up to 100 000). Importantly, this catalytic asymmetric hydrogenation with a DKR process provided a highly efficient and powerful synthetic strategy for the preparation of key chiral intermediates of the preclinical antitumor agent (S,S)-R116010.

Copper bromide reagent and its preparation method, α--aminobenzene acetone and its process for synthesis of derivatives of

The invention discloses a copper bromide reagent, a preparation method thereof, and a synthesis method of alpha-amido propiophenone and derivative thereof. Copper bromide cheap in industry and 2,6-bi[4-(1,1-dimethyl)-2-oxazoline-2-base] pyridine react to directly obtain high yield of high-purity copper bromide reagent, in addition, the copper bromide reagent and propiophenone containing multiple important functional groups have good reaction activity. Due to the characteristic, high yield of alpha-amido propiophenone and derivative thereof can be obtained in mild conditions, conventional expensive azoic compound materials are not used, the cost is lowered to a large extent, the operation requirement is also lowered, and alpha-amido propiophenone and derivative thereof have good application prospect in industry.

Electrochemically Oxidative α-C-H Functionalization of Ketones: A Cascade Synthesis of α-Amino Ketones Mediated by NH4I

An efficient electrochemical protocol for the synthesis of α-amino ketones via the oxidative cross-dehydrogenative coupling of ketones and secondary amines has been developed. The electrochemistry performs in a simple undivided cell using NH4I

N-Bromosuccinimide promoted and base switchable one pot synthesis of α-imido and α-amino ketones from styrenes

An N-Bromosuccinimide (NBS) promoted one pot strategy for the synthesis of α-amino functionalized aryl ketones starting from commercially available styrenes has been developed. NBS participates in multiple tasks, such as bromonium ion formation, oxidation of bromohydrin and providing a nucleophilic nitrogen source. The reaction can easily be switched between α-imido and α-amino ketones by the choice of base. This one pot strategy was successfully applied for the synthesis of psychoactive drug candidates, amfepramone, mephedrone and 4-MEC.

A two-step continuous synthesis of α-ketoamides and α-amino ketones from 2° benzylic alcohols using hydrogen peroxide as an economic and benign oxidant

A practical two-step synthesis of α-ketoamides and α-amino ketones via direct oxidative coupling between 2° benzylic alcohols and amines was developed. Hydrogen peroxide, an economic and environmentally friendly oxidant, was used, and a metal catalyst was unnecessary. Moreover, the continuous-flow technique was employed to increase the functional group tolerance, efficiency and safety.

A versatile and one-pot strategy to synthesize ?±-amino ketones from benzylic secondary alcohols using N -bromosuccinimide

A metal-free one-pot strategy has been developed for the first time to synthesize pharmaceutically important ?±-amino ketones from readily available benzylic secondary alcohols and amines using N-bromosuccinimide. This new reaction proceeds via three consecutive steps involving oxidation of alcohols, ?±-bromination of ketones, and nucleophilic substitution of ?±-bromo ketones to give ?±-amino ketones. Importantly, this novel one-pot greener reaction avoids direct usage of toxic and corrosive bromine. This methodology has been employed efficiently to synthesize pharmaceutically important amfepramone and pyrovalerone in a single step.

Synthesis and characterization of bisoxazolines- and pybox-copper(II) complexes and their application in the coupling of α-carbonyls with functionalized amines

Binuclear complexes [{(DMOX)CuCl}2(μ-Cl)2] (1), mononuclear complexes [(DMOX)CuBr2] (2) (DMOX = 4,5-dihydro-2-(4,5- dihydro-4,4-dimethyloxazol-2-yl)-4,4-dimethyloxazole) and the pybox Cu(ii) complex [(Dm-Pybox)CuBr2/

Transition-metal-free oxidative α-C-H amination of ketones via a radical mechanism: Mild synthesis of α-amino ketones

A transition-metal-free direct α-C.H amination of ketones has been developed using commercially available ammonium iodide as the catalyst and sodium percarbonate as the co-oxidant. A wide range of ketone ((hetero)aromatic or nonaromatic ketones) and amine (primary/secondary amines, anilines, or amides) substrates undergo cross-coupling to generate synthetically useful α-amino ketones. The mechanistic studies indicated that a radical pathway might be involved in the reaction process. The utility of the method is highlighted through a concise one-step synthesis of the pharmaceutical agent amfepramone.

Simple catalytic mechanism for the direct coupling of α-carbonyls with functionalized amines: A one-step synthesis of plavix

The direct α-amination of ketones, esters, and aldehydes has been accomplished via copper catalysis. In the presence of catalytic copper(II) bromide, a diverse range of carbonyl and amine substrates undergo fragment coupling to produce synthetically useful α-amino-substituted motifs. The transformation is proposed to proceed via a catalytically generated α-bromo carbonyl species; nucleophilic displacement of the bromide by the amine then delivers the α-amino carbonyl adduct while the catalyst is reconstituted. The practical value of this transformation is highlighted through one-step syntheses of two high-profile pharmaceutical agents, Plavix and amfepramone.