37629-51-9

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(4-METHOXYPHENYL)-2-NITROPROPENE is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used as a Precursor in Organic Chemistry:
In the field of organic chemistry, 1-(4-METHOXYPHENYL)-2-NITROPROPENE serves as a precursor for the production of other organic compounds. Its reactivity and functional groups make it a valuable component in the synthesis of a wide range of chemical products, including specialty chemicals, agrochemicals, and advanced materials.

InChI:InChI=1/C10H11NO3/c1-8(11(12)13)7-9-3-5-10(14-2)6-4-9/h3-7H,1-2H3/b8-7+

Upstream product

• 79-24-3 Nitroethane 
• 123-11-5 4-methoxy-benzaldehyde 
• 148527-33-7 2-nitro-1-hydroxy-1-(4-methoxy-phenyl)-propane 
• 13048-81-2 (E)-3-(4-methoxyphenyl)-2-methylacrylic acid 
• 105-13-5 4-Methoxybenzyl alcohol 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 591-31-1 3-methoxy-benzaldehyde 
• 104-46-1 anethole 
• 148527-35-9 1-(4-methoxyphenyl)-2-nitropropyl acetate 

Downstream Products

• 64-13-1 2-amino-1-(4-methyoxyphenyl)propane 
• 100780-39-0 t-Butyl 3-(p-methoxy-phenyl)-4-methylpyrrole-2-carboxylate 
• 29865-49-4 2-nitro-1-(4-methoxylphenyl) propane 
• 69390-41-6 (E)-N-(1-(4-methoxyphenyl)prop-1-en-2-yl)acetamide 
• 69390-41-6 (Z)-N-(1-(4-methoxyphenyl)prop-1-en-2-yl)acetamide 
• 124901-14-0 ethyl 4-methyl-3-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate 
• 142865-84-7 (4RS,5SR,6SR)-4-(4-methyloxyphenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-4H-benzo[e]-1,2-oxazine N-oxide 
• 95021-29-7 3-[1-(4-methoxyphenyl)-2-nitropropyl]-1H-indole 
• 298193-39-2 2-(4-methoxyphenyl)-3-methylimidazo[1,2-a]pyridine 

Relevant academic research and scientific papers

Discovery of Cytochrome P450 4F11 Activated Inhibitors of Stearoyl Coenzyme A Desaturase

Stearoyl-CoA desaturase (SCD) catalyzes the first step in the conversion of saturated fatty acids to unsaturated fatty acids. Unsaturated fatty acids are required for membrane integrity and for cell proliferation. For these reasons, inhibitors of SCD represent potential treatments for cancer. However, systemically active SCD inhibitors result in skin toxicity, which presents an obstacle to their development. We recently described a series of oxalic acid diamides that are converted into active SCD inhibitors within a subset of cancers by CYP4F11-mediated metabolism. Herein, we describe the optimization of the oxalic acid diamides and related N-acyl ureas and an analysis of the structure-activity relationships related to metabolic activation and SCD inhibition.

Catalyst- and Substituent-Controlled Switching of Chemoselectivity for the Enantioselective Synthesis of Fully Substituted Cyclobutane Derivatives via 2 + 2 Annulation of Vinylogous Ketone Enolates and Nitroalkene

The first regioselective, diastereoselective, and enantioselective organocatalyzed Michael-Michael cascade of vinylogous ketone enolates and nitroalkenes for the construction of fully substituted cyclobutanes is achieved by the deployment of the appropriate chiral squaramide catalyst and the pertinent substituent on the substrate. The domino reaction provided cyclobutanes with four contiguous stereocenters, including a quaternary center in good yields with diastereomeric ratio of >20:1 and with enantioselectivities of mostly up to 98% enantiomeric excess (ee). The structures and the absolute configurations of the adducts were confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.

INDOLE AHR INHIBITORS AND USES THEREOF

The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.

Catalytic asymmetric Tamura cycloadditions involving nitroalkenes

The first examples of asymmetric Tamura cycloaddition reactions involving singly activated alkenes are reported. Homophthalic anhydride reacts with α-methyl nitrosytrenes in the presence of an alkaloid-based catalyst to generate fused bicyclic aromatic ketone products with three new stereocentres (which are susceptible to subsequent equilibration) in 12-99% ee. An unusual equilibration process which occurs in methanolic medium in the absence of a recognisable base via proton transfer at the α-carbon of an ester was investigated experimentally and computationally.

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.

One-pot solid phase synthesis of (E)-nitroalkenes

An efficient one-pot protocol for the synthesis of (E)-nitroalkenes by reaction of aldehydes and nitroalkanes in the presence of polymer-bound triphenylphosphine, iodine and imidazole is described. Although the reaction works with similar efficiency with triphenylphosphine and its polymer-bound version, easy removal of the unwanted polymer-bound triphenylphosphine oxide and its recovery as triphenylphosphine provide the edge for practical application of the method.

Synthesis of nitroalkenes involving a cooperative catalytic action of iron(III) and piperidine: A one-pot synthetic strategy to 3-alkylindoles, 2H-chromenes and N-arylpyrrole

An efficient and simple strategy has been developed to synthesize various substituted nitroalkenes involving a cooperative catalytic system of FeCl 3 and piperidine. This dual catalytic protocol simultaneously activates both electrophile and nucleophile and works under mild reaction conditions so that many sensitive functional groups were tolerated. Moreover, this cooperative catalytic reaction is also suitable for various one-pot reactions involving nitroalkenes such as, 2H-chromenes, N-arylpyrrole and Michael reaction with indole. Notably, this method is low-cost, efficient and environmentally friendly. Copyright

Design of phosphorus ligands with deep chiral pockets: Practical Synthesis of chiral β-arylamines by asymmetric hydrogenation

WingPhos, a C2-symmetric bisphosphorus ligand with a deep and well-defined chiral pocket was developed. It has shown high efficiency in the rhodium-catalyzed asymmetric hydrogenation of (E)-β-aryl-N-acetyl enamides, cyclic β-aryl enamides, and heterocyclic β-aryl enamides. A series of chiral β-arylisopropylamines, 2-aminotetralines, and 3-aminochromans can be synthesized with excellent ee values (nbd=3,5-norbornadiene; TON=turnover number). Copyright

One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes through a catalytic tandem reaction using an amino acid lithium salt

One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes was achieved by a catalytic tandem reaction using a primary amino acid lithium salt, O-tert-butyldiphenylsilyl l-tyrosine lithium salt, as a catalyst. Various aryl, alkenyl, and alkyl aldehydes were converted into γ-nitroaldehydes via in situ generation of nitroalkenes.

New rearrangement of conjugated cyclic ene nitroso O-trimethylsilyl acetals: Convenient synthesis of dihydro-2H-pyran-3-one and dihydrofuran-3-one oximes

The nucleophile-induced rearrangement of cyclic N-alkoxy-N-(silyloxy) enamines was investigated. As a result, a new strategy for the synthesis of β-pyranone and β-furanone derivatives from nitro compounds is suggested. Georg Thieme Verlag Stuttgart New Yo