40748-84-3

Upstream product

• 40748-86-5 1-(3-Cyclohexen-1-yl)-2-nitroethylacetat 
• 75-52-5 nitromethane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 50598-92-0 (E)-(2-nitrovinyl)cyclohexane 
• 100-50-5 3-Cyclohexene-1-carboxaldehyde 
• 141377-56-2 1-cyclohexyl-2-nitroethanol 
• 50598-92-0 2-cyclohexyl-1-nitroethene 

Downstream Products

• 183657-58-1 2-Cyclohexyl-1-nitro-ethanone oxime 
• 1144110-53-1 (R)-1-(4-cyclohexyl-3-nitro-1-(phenylsulfonyl)butylsulfonyl)benzene 
• 1312540-68-3 3-(cyclohexylmethyl)isoxazole-4-carbaldehyde 
• 102588-25-0 (E)-N,N-Bis(tert-butyldimethylsiloxy)-2-cyclohexylethen-1-amin 
• 183657-81-0 C₂₁H₂₂N₂O₄ 
• 4435-14-7 2-cyclohexylacetonitrile 

Relevant academic research and scientific papers

Organocatalytic biomimetic reduction of conjugated nitroalkenes

A thiourea-catalyzed biomimetic reduction of conjugated nitroalkenes has been developed. Various aromatic and aliphatic conjugated nitroalkenes can be reduced to give the respective nitroalkanes with good yields under mild conditions. This protocol is not only practical, but may also provide insight into the mechanisms of redox transformations in biological systems. Georg Thieme Verlag Stuttgart.

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.

Useful extensions of the henry reaction: Expeditious routes to nitroalkanes and nitroalkenes in aqueous media

The products of the Henry nitroaldol reaction from nitromethane and several aldehydes were reduced to the corresponding nitroalkanes with (n-Bu) 3SnH in water under microwave irradiation (80 °C/10 min), or dehydrated to the corresponding nitroalkenes with K2CO3 in water (generally 0-5 °C/20 min). Both "one-pot" reactions occur in excellent yields across a range of aliphatic and aromatic (including heteroaromatic) substrates. It seems likely that the deoxygenation of the nitroaldols occurs via coordination of an oxygen atom of the nitro group with a tin atom, which facilitates hydride delivery in the transition state. The elimination of water from the nitroaldols in mild base is likely driven by the stability of the conjugated nitroalkene products. The elimination required workup with 2 N HCl, which likely displaces a nitroalkane-nitroalkene equilibrium towards the latter. These extensions of the Henry reaction lead to products not easily obtained otherwise.

Functional-group tolerance in frustrated lewis pairs: hydrogenation of nitroolefins and acrylates

Weak Lewis acid for high nucleophilicity: Hydridoborate derived from B(2,6-F2C6H3)3 shows significant hydride character. Solid-state and solution structure analysis revealed a dihydrogen-bonded aggregate. The new frustrated Lewis pair was applied in the hydrogenation of nitroolefins and acrylates (see scheme; EWG=electron- withdrawing group). The decreased Lewis acidity provides higher reactivity and functional-group tolerance. Copyright

Cascade formation of isoxazoles: Facile base-mediated rearrangement of substituted oxetanes

Give me five! Nitro compounds and oxetan-3-one react through an intriguing cascade sequence to give isoxazole-4-carbaldehydes using inexpensive reagents in a one-pot procedure (see scheme; Ms=methanesulfonyl). A variety of 3-substituted isoxazole-4-carbaldehydes were obtained in high overall yields.

Catalyst-free and solventless Hantzsch ester mediated reduction of nitroolefins at elevated temperature

A catalyst-free and solventless protocol for the reduction of nitroolefins to the corresponding nitroalkanes at 100°C has been developed. Various nitroalkenes have been reduced in good to excellent yield with short reaction times.