61668-44-8

Upstream product

• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 25695-90-3 [(E)-(2-nitrobut-1-en-1-yl)benzene] 
• 108-03-2 1-Nitropropane 
• 1202-32-0 2-Nitro-1-phenyl-1-butene 
• 60984-51-2 (Z)-1-phenyl-2-nitro-1-butene 

Downstream Products

• 19013-50-4 2-benzyl-3-methyl-1H-indole 
• 78825-91-9 2-ethyl-3-phenyl-1H-indole 
• 1007-32-5 benzyl ethyl ketone 

Relevant academic research and scientific papers

Volatile Flavor Constituents of Fruits from Southern Africa: Mobola Plum (Parinari curatellifolia)

The volatile flavor components of Mobola plum (Parinari curatellifolia), a native fruit of Southern Africa, have been isolated by a vacuum headspace concentration method. The concentrate was analyzed by hyphenated gas chromatographic techniques, including gas chromatography (GC)/mass spectrometry (MS) and GC/Fourier transform infrared (FTIR), together with other GC-coupled detection devices for the specific and selective detection of nitrogen- and sulfur-containing compounds. A total of 88 components were identified. Of these compounds, 12 contain nitrogen, including 2-aminobenzaldehyde and phenylacetaldoxime, which are detected for the first time in an edible fruit. In addition, two unusual nitrated compounds have been identified, including optically active (2-nitrobutyl)benzene, which is a new natural product. Quantitative and sensory data of the new compounds are provided.

Enantioselective hydrogenation of α,β-disubstituted nitroalkenes

The first highly chemo- and enantioselective hydrogenation of α,β-disubstituted nitroalkenes was accomplished with rhodium/JosiPhos-J2 as a catalyst, with the yield and enantioselectivity of up to 95% and 94%, respectively. The α-chiral nitroalkanes will provide an entry to valuable chiral amphetamines which are otherwise not so easily accessed. This journal is the Partner Organisations 2014.

Benzylation of nitroalkanes using copper-catalyzed thermal redox catalysis: Toward the facile C-alkylation of nitroalkanes

The C-alkylation of nitroalkanes under mild conditions has been a significant challenge in organic synthesis for more than a century. Herein we report a simple Cu(I) catalyst, generated in situ, that is highly effective for C-benzylation of nitroalkanes using abundant benzyl bromides and related heteroaromatic compounds. This process, which we believe proceeds via a thermal redox mechanism, allows access to a variety of complex nitroalkanes under mild reaction conditions and represents the first step toward the development of a general catalytic system for the alkylation of nitroalkanes.

Asymmetric reduction of nitroalkenes with baker's yeast

Various α,β-disubstituted and trisubstituted nitroalkenes were chemoselectively reduced with baker's yeast to the corresponding nitroalkanes. Stereoselectivities of the reduction of α,β-disubstituted nitroalkenes were modest to low, and e.e.s up to 52% were obtained. Trisubstituted nitroalkenes could be reduced to the corresponding nitroalkanes with excellent enantioselectivities, moderate diastereoselectivities and in good yield.

In Situ Generation and Synthetic Application of 2-Phenylbenzimidazoline to the Selective Reduction of Carbon-Carbon Double Bonds of Electron-Deficient Olefins

2-Phenylbenzimidazoline (PBI) as a mild, selective, and convenient reducing agent was efficiently generated in situ from o-phenylenediamine and benzaldehyde in alcohols.A generally applicable method for the selective reduction of carbon-carbon double bonds of a variety of electron-deficient olefins with an alcoholic solution of PBI is described.The reduction of α,β-unsaturated ketones to the corresponding saturated ketones could also be accomplished (but, less effectively) with PBI with the aid of a Lewis-acid catalyst. 1-Methyl-2-(o-nitrophenyl)benzimidazoline prepared and isolated by the reaction of o-nitrobenzaldehyde with N-methyl-o-phenylenediamine reduced benzylidenemalononitrile to give benzylmalononitrile and 1-methyl-2-(o-nitrophenyl)benzimidazoline in high yields.This shows the validity of PBI to be the actual reducing species in the present reduction system.From a mechanistic study, the present reductions could be interpreted in terms of a mechanism involving a synchronous transport of a pair of hydrogens or a sequential transfer of a hydride and a proton from PBI to the olefins.