17322-34-8

Usage

InChI:InChI=1/C9H11NO2/c1-8(10(11)12)7-9-5-3-2-4-6-9/h2-6,8H,7H2,1H3

Upstream product

• 705-60-2 (2-nitroprop-1-enyl)benzene 
• 2114-39-8 (2-bromopropyl)-benzene 
• 79-24-3 Nitroethane 
• 66310-10-9 N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate 
• 26251-08-1 2-nitro-1-phenylpropan-1-ol 
• 83705-50-4 C₉H₁₀NO₂^(1-) 
• 100-52-7 benzaldehyde 
• 63-90-1 N-hydroxy-1-phenyl-2-propylamine 
• 58321-79-2 (Z)-(2-nitroprop-2-en-1-yl)benzene 
• 60-15-1 2-amino-1-phenylpropane 
• 705-60-2 1-phenyl-2-nitroprop-1-ene 
• 60-29-7 diethyl ether 
• 29527-87-5 (2-iodopropyl)benzene 
• 100-51-6 benzyl alcohol 

Downstream Products

• 91152-56-6 3,4-dimethyl-4-nitro-5-phenylpentanenitrile 
• 115412-38-9 4-(1-Methyl-1-nitro-2-phenyl-ethyl)-furan-2-carboxylic acid methyl ester 
• 83565-90-6 C₁₇H₁₉NO₃S 
• 83659-69-2 3-methyl-3-nitro-4-phenyl-1-butene 
• 71831-62-4 2,6-Dimethyl-4'-(1-methyl-1-nitro-2-phenyl-ethyl)-4'H-[1,1']bipyridinyl-4-one 
• 4797-81-3 N-benzyloxyacetamide 
• 83705-50-4 C₉H₁₀NO₂^(1-) 
• 54704-34-6 L-1-methyl-2-cyclohexylethylamine 
• 145050-40-4 N-Ethylidene-1-methyl-2-phenylethylamine 
• 60-15-1 2-amino-1-phenylpropane 
• 103-79-7 1-phenyl-acetone 
• 89706-88-7 4-Methyl-4-nitro-1,3,5-triphenyl-pentan-1-one 
• 97763-91-2 4-Methyl-4-nitro-5-phenyl-pentanal 
• 97763-90-1 2,4-Dimethyl-4-nitro-5-phenyl-pentanenitrile 

Relevant academic research and scientific papers

Asymmetric reduction of α,β-unsaturated ketones with a carbon-carbon double-bond reductase from baker's yeast

A novel carbon-carbon double-bond reductase was isolated from the cells of baker's yeast. The reduction of α,β-unsaturated ketones catalyzed by this enzyme affords the corresponding saturated (S)-ketones selectively.

THE NON-CHAIN RADICALOID C-ALKYLATION OF NITRONATE ANIONS: FURTHER EVIDENCE FOR THE MECHANISM

The effects of the variation of solvent, pyridinium leaving group, N-substituent, and nitronate nucleophile have been studied in the C-alkylation of nitronate anions.These variations and studies of the effects of inhibitors, attempted entrainment reactions, and ESR work are all in accord with our previously suggested mechanism.

Sodium Borohydride Reduction of Nitrostyrenes by Reverse Addition: A Simple and Efficient Method for the Large-Scale Preparation of Phenylnitroethanes

Reverse addition of nitrostyrenes 1 to sodium borohydride in dioxan/ethanol gives phenylnitroethanes 3 in very good yields.

MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR

This disclosure provides modulators of Cystic Fibrosis Transmembrane Conductance Regulator (CFTR), pharmaceutical compositions containing at least one such modulator, methods of treatment of cystic fibrosis using such modulators and pharmaceutical compositions, and processes for making such modulators.

Expanding the Biocatalytic Toolbox with a New Type of ene/yne-Reductase from Cyclocybe aegerita

This study introduces a new type of ene/yne-reductase from Cyclocybe aegerita with a broad substrate scope including aliphatic and aromatic alkenes/alkynes from which aliphatic C8-alkenones, C8-alkenals and aromatic nitroalkenes were the preferred substrates. By comparing alkenes and alkynes, a ～2-fold lower conversion towards alkynes was observed. Furthermore, it could be shown that the alkyne reduction proceeds via a slow reduction of the alkyne to the alkene followed by a rapid reduction to the corresponding alkane. An accumulation of the alkene was not observed. Moreover, a regioselective reduction of the double bond in α,β-position of α,β,γ,δ-unsaturated alkenals took place. This as well as the first biocatalytic reduction of different aliphatic and aromatic alkynes to alkanes underlines the novelty of this biocatalyst. Thus with this study on the new ene-reductase CaeEnR1, a promising substrate scope is disclosed that describes conceivably a broad occurrence of such reactions within the chemical landscape.

Iridium-catalyzed highly chemoselective and efficient reduction of nitroalkenes to nitroalkanes in water

An iridium-catalyzed highly chemoselective and efficient transfer hydrogenation reduction of structurally diverse nitroalkenes was realized at very low catalyst loading (S/C = up to 10000 or 20?000), using formic acid or sodium formate as a traceless hydride donor in water. Excellent functionality tolerance is also observed. The turnover number and turnover frequency of the catalyst reach as high as 18?600 and 19?200 h-1, respectively. An inert atmosphere protection is not required. The reactivities of nitroalkenes are dependent on their substitution pattern, and the pH value is a key factor to accomplish the complete conversion and excellent chemoselectivity. Purification of products is achieved by simple extraction without column chromatography. The reduction procedure is facilely amplified to 10 g scale at 10?000 S/C ratio. The potential of this green reduction in enantioselective hydrogenation has been demonstrated.

Method for high-selectivity reduction of nitroolefin C=C double bonds

The invention provides a method for high-selectivity reduction of nitroolefin C=C double bonds. According to the method, a bidentate nitrogen ligand-[Cp* IrCl2] complex is used as the catalyst, nitroolefin can be conveniently converted into nitroalkane, the catalytic efficiency is extremely high, and the substrate conversion rate is 99% or above. The high-purity nitroalkane can be separated through simple extraction, liquid separation and solvent removal under reduced pressure. The selected solvent is water or a mixture of water and a hydrophilic solvent. The method is green, environment-friendly and high in reaction efficiency. The nitroalkane compound prepared by the invention is a very important organic intermediate, and has wide application in the fields of national defense, pesticide, biology, medicine, fine chemical engineering and the like.

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.

Synthesis of Isoxazolines from Nitroalkanes via a [4+1]-Annulation Strategy

A novel access to isoxazolines was developed using the [4+1]-annulation of α-keto-stabilized sulfur ylides with N,N-bis(siloxy)enamines derived from aliphatic nitro compounds. The resulting 5-keto-substituted isoxazolines were shown to be convenient precursors of polysubstituted 3-hydroxypyrrolidines via the one-pot catalytic N?O hydrogenolysis/intramolecular reductive amination sequence. Application of this approach to the formal synthesis of Merck's potent NK1 receptor antagonist was demonstrated. (Figure presented.).

Ligand-Enabled meta-Selective C-H Arylation of Nosyl-Protected Phenethylamines, Benzylamines, and 2-Aryl Anilines

A Pd-catalyzed, meta-selective C-H arylation of nosyl-protected phenethylamines and benzylamines is disclosed using a combination of norbornene and pyridine-based ligands. Subjecting nosyl protected 2-aryl anilines to this protocol led to meta-C - H arylation at the remote aryl ring. A diverse range of aryl iodides are tolerated in this reaction, along with select heteroaryl iodides. Select aryl bromides bearing ortho-coordinating groups can also be utilized as effective coupling partners in this reaction. The use of pyridine ligands has allowed the palladium loading to be reduced to 2.5 mol %. Furthermore, a catalytic amount of 2-norbomene (20 mol %) to mediate this meta-C - H activation process is demonstrated for the first time. Utilization of a common protecting group as the directing group for meta-C-H activation of amines is an important feature of this reaction in terms of practical applications.