78579-86-9

Upstream product

• 79918-52-8 ethyl 2-nitro-5-phenyl-4-pentenoate 
• 1821-12-1 4-Phenylbutyric acid 
• 122-97-4 3-Phenyl-1-propanol 
• 75-52-5 nitromethane 
• 4119-41-9 1-iodo-3-phenylpropan 
• 2270-20-4 5-Phenylpentanoic acid 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 104-53-0 3-phenyl-propionaldehyde 
• 80922-14-1 1-nitro-4-phenylbut-1-ene 
• 141377-53-9 1-nitro-4-phenylbutan-2-ol 
• 80922-14-1 (E)-(4-nitrobut-3-enyl)benzene 
• 173409-92-2 3-nitro-1,6-diphenyl-2-hexen-1-one 

Downstream Products

• 173409-92-2 3-nitro-1,6-diphenyl-2-hexen-1-one 
• 173409-88-6 (E)-1,6-diphenyl-2-hexen-1-one 
• 495-71-6 phenacylacetophenone 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 556782-58-2 3-(3-phenyl-propyl)-5-(tetrahydro-pyran-2-yloxymethyl)-isoxazole 
• 1022991-29-2 (2R,3R)-methyl 2-(4-methoxyphenylamino)-3-nitro-6-phenylhexanoate 
• 75056-45-0 N-(1-phenylethyl)-4-phenylbutyramide 
• 78172-94-8 N-benzyl-N-methyl-4-phenylbutanamide 
• 56229-85-7 N,N-diethyl-4-phenylbutanamide 

Relevant academic research and scientific papers

Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles

A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).

Nitroalkene reduction in deep eutectic solvents promoted by BH3NH3

Deep eutectic solvents (DESs) have gained attention as green and safe as well as economically and environmentally sustainable alternative to the traditional organic solvents. Here, we report the combination of an atom-economic, very convenient and inexpensive reagent, such as BH3NH3, with bio-based eutectic mixtures as biorenewable solvents in the synthesis of nitroalkanes, valuable precursors of amines. A variety of nitrostyrenes and alkyl-substituted nitroalkenes, including α- and β-substituted nitroolefins, were chemoselectively reduced to the nitroalkanes, with an atom economy-oriented, simple and convenient experimental procedure. A reliable and easily reproducible protocol to isolate the product without the use of any organic solvent was established, and the recyclability of the DES mixture was successfully investigated.

Modular Synthesis of Carbon-Substituted Furoxans via Radical Addition Pathway. Useful Tool for Transformation of Aliphatic Carboxylic Acids Based on "build-and-Scrap" Strategy

Utilizing radical chemistry, a new general C-C bond formation on the furoxan ring was developed. By taking advantage of the lability of furoxans, a wide variety of transformation of the synthesized furoxans have been demonstrated. Thus, this developed methodology enabled not only the modular synthesis of furoxans but also short-step transformations of carboxylic acids to a broad range of functional groups.

Nickel-Catalyzed C-Alkylation of Nitroalkanes with Unactivated Alkyl Iodides

Enabled by nickel catalysis, a mild and general catalytic method for C-alkylation of nitroalkanes with unactivated alkyl iodides is described. Compatible with primary, secondary, and tertiary alkyl iodides; and tolerant of a wide range of functional groups, this method allows rapid access to diverse nitroalkanes.

Catalytic Access to Alkyl Bromides, Chlorides and Iodides via Visible Light-Promoted Decarboxylative Halogenation

Herein is reported the catalytic, visible light-promoted, decarboxylative halogenation (bromination, chlorination, and iodination) of aliphatic carboxylic acids. This operationally-simple reaction tolerates a range of functional groups, proceeds at room temperature, and is redox neutral. By employing an iridium photocatalyst in concert with a halogen atom source, the use of stoichiometric metals such as silver, mercury, thallium, and lead can be circumvented. This reaction grants access to valuable synthetic building blocks from the large pool of cheap, readily available carboxylic acids.

Oxidative Amidation of Nitroalkanes with Amine Nucleophiles using Molecular Oxygen and Iodine

The formation of amides and peptides often necessitates powerful yet mild reagent systems. The reagents used, however, are often expensive and highly elaborate. New atom-economical and practical methods that achieve such goals are highly desirable. Ideally, the methods should start with substrates that are readily available in both chiral and non-chiral forms and utilize cheap reagents that are compatible with a wide variety of functional groups, steric encumberance, and epimerizable stereocenters. A direct oxidative method was developed to form amide and peptide bonds between amines and primary nitroalkanes simply by using I2 and K2CO3 under O2. Contrary to expectations, a 1:1 halogen-bonded complex forms between the iodonium source and the amine, which reacts with nitronates to form α-iodo nitroalkanes as precursors to the amides.

Catalytic transfer hydrogenation of conjugated nitroalkenes using decaborane: Synthesis of oximes

The reduction of α,β-unsaturated nitroalkenes was attempted using a system of decaborane and DMSO in methanol in the presence of 10% Pd/C at rt under nitrogen. As a result, the corresponding oximes were generated in good to high yields.

Generation of α-Nitroalkyl Radicals by Oxidation of Nitronate Anions with Cerium(IV) Ammonium Nitrate and Their Addition Reaction to Electron-Rich Olefins

α-Nitroalkyl radicals are generated by oxidation of nitronate anions with cerium(IV) ammonium nitrate.When the reactions are carried out in hte presence of electron-rich olefins, such as silyl enol ethers, intermolecular addition of the radicals proceeds to afford β-nitroketones, which are further converted to α,β-unsaturated ketones in good yield.