63099-53-6

Upstream product

• 100-19-6 (4-nitrophenyl)ethanone 
• 769-59-5 3-phenyl-butan-2-one 
• 98-95-3 nitrobenzene 
• 78-93-3 butanone 
• 50434-36-1 4-nitrophenylacetyl chloride 
• 598-32-3 2-hydroxy-3-butene 
• 5332-96-7 1-(4-nitrophenyl)propan-2-one 
• 74-88-4 methyl iodide 

Downstream Products

• 63099-46-7 Trifluoro-methanesulfonic acid (Z)-1-methyl-2-(4-nitro-phenyl)-propenyl ester 
• 63099-40-1 Trifluoro-methanesulfonic acid (E)-1-methyl-2-(4-nitro-phenyl)-propenyl ester 
• 485842-62-4 (S)-1-(4-nitrophenyl)ethyl acetate 
• 1240659-45-3 1,1-dimethyl-2-(3-(4-nitrophenyl)butan-2-ylidene)hydrazine 
• 72511-00-3 3-(p-nitrophenyl)-2-butanone oxime 
• 1309380-95-7 C₂₀H₁₈N₂O₅S 

Relevant academic research and scientific papers

Dynamic Reductive Kinetic Resolution of Benzyl Ketones using Alcohol Dehydrogenases and Anion Exchange Resins

Dynamic reductive kinetic resolutions of racemic 3-arylalkanones have been performed by the proper combination of an alcohol dehydrogenase and a basic anionic resin. The best results were found for the bioreduction with the alcohol dehydrogenase type A from Rhodococcus ruber DSM 44541 overexpressed in Escherichia coli (E. coli/ADH-A) and the commercially available evo-1.1.200, while the Amberlite IRA-440 C and the DOWEX-MWA-1 resins allowed efficient in situ racemizations. Reaction conditions were optimized in terms of enzyme source and loading, type and amount of resin, pH, temperature and reaction times, obtaining a series of (R,R)-substituted propan-2-ols with good conversions and both diastereoselectivity and stereoselectivity. As a proof of concept, the subsequent intramolecular cyclization of a selected propan-2-ol substrate afforded a valuable isochroman heterocycle without any loss of the optical purity.

Aerobic, transition-metal-free, direct, and regiospecific mono-α-arylation of ketones: Synthesis and mechanism by DFT calculations

We disclose a facile, aerobic, transition-metal-free, direct, and regiospecific mono-α-arylation of ketones to yield aryl benzyl and (cyclo)alkyl benzyl ketones with substitution patterns that are currently inaccessible or challenging to prepare using conventional methods. The transformation is operationally simple, scalable, and environmentally friendly. There is no need for pre-functionalization (i.e., α-halogenation or silyl enol ether formation) or the use of specialized arylating agents (i.e., diaryliodonium salts). DFT calculations suggest that the in situ-generated enolate undergoes direct C-C bond formation with the nitroarene followed by regioselective O2-mediated C-H oxidation.

Fe(II)-catalyzed amination of aromatic C-H bonds via ring opening of 2 H-azirines: Synthesis of 2,3-disubstituted indoles

A general method for the synthesis of 2,3-disubstituted indoles is described. The key feature of this method is the amination of aromatic C-H bonds via FeCl2-catalyzed ring opening of 2H-azirines. The method tolerates a variety of functional groups such as Br, F, NO2, OMe, CF3, OTBS, alkenes, and OPiv. The method can also be extended to synthesize azaindoles.

Baeyer-Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters

The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic α-alkyl benzylketones with longer alkyl chains as well as with two substituted α-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis.

Arenediazonium o-benzenedisulfonimides in Heck-type arylation of allylic alcohols

Arenediazonium o-benzenedisulfonimides were reacted with primary and secondary allylic alcohols. The reactions, carried out in aqueous ethanol in the presence of palladium(II) acetate as precatalyst and sodium hydrogen carbonate as base, gave the arylation products with good overall conversion. In all cases, the major products were the β-arylated carbonyl derivatives. The o-benzene-disulfonimide was recovered in high yield from all the reactions, and it was recycled for the preparation of other salts. Georg Thieme Verlag Stuttgart.

Electrochemical synthesis of nitroaromatic ketones

Nitroaromatic ketones are readily prepared by nucleophilic aromatic substitution of hydrogen in nitroarenes by electrochemical oxidation. Carbanions of various ketones were added to selected nitroarenes in DMF/ketone mixtures leading to formation of the o

ETUDE STEREOCHIMIQUE DE L'ALKYLATION D'ANIONS PAR DES DERIVES p-NITROBENZYLIQUES OPTIQUEMENT ACTIFS COMPETITION SN2-SNR1

Competittion between SRN1, SN2 and SRN2 mechanisms is discussed according to the stereochemical results in the alkylation of anions by optically active secondary p-nitrobenzyl reagents.Results from alkylation of the anions