13414-54-5

Usage

InChI:InChI=1/C10H11NO3/c1-8(2)7-14-10-6-4-3-5-9(10)11(12)13/h3-6H,1,7H2,2H3

Upstream product

• 88-75-5 2-hydroxynitrobenzene 
• 563-47-3 3-Chloro-2-methylpropene 
• 1458-98-6 2-methyl-3-bromo-1-propene 
• 91-23-6 2-Nitroanisole 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 1493-27-2 ortho-nitrofluorobenzene 

Downstream Products

• 55000-14-1 2-[(2-methyl-2-propenyl)oxy]benzamine 
• 13414-55-6 2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran 
• 5330-66-5 1-(2-nitrophenoxy)-propan-2-one 
• 55000-08-3 1-azido-2-(2-methylallyloxy)benzene 

Relevant academic research and scientific papers

Boron-Promoted Ether Interchange Reaction: Synthesis of Alkyl Nitroaromatic Ethers from Methoxynitroarenes

The first protocol for boron-promoted ether interchange reaction of methoxynitroarenes was described. A series of methoxynitroarenes and alcohols, including primary, secondary, as well as tertiary alcohols were reacted smoothly in moderate to good yields under the optimized reaction conditions. This protocol constitutes an operationally simple and scalable strategy for the synthesis of alkyl nitroaromatic ethers. Moreover, the new reactivity of boron reagents was discovered.

Pd-Catalyzed Enantioselective Double Heck Reaction

An asymmetric Pd-catalyzed intramolecular followed by an intermolecular double Heck reaction of arenediazonium salts with simple alkenes is disclosed. This reaction features mild reaction conditions, simple operation, and excellent functional group tolera

Cyclizing radical carboiodination, carbotelluration, and carboaminoxylation of aryl amines

Radical carboiodination of various aryl amines is reported. Aryl diazonium salts, generated in situ from the corresponding aryl amines, are reacted with Bu4NI to provide the corresponding aryl radicals which undergo 5-exo or 6-exo cyclization. Iodine abstraction eventually affords the carboiodinated products in good to excellent yields. If TEMPO is added, the cascade provides the cyclized carboaminoxylation products. Running the reaction in the presence of PhTeTePh affords the phenyltellurated cyclized products.

NITRILES AND MEDICINAL COMPOSITIONS CONTAINING THE SAME AS THE ACTIVE INGREDIENT

The present invention relates to a compound of formula (I) wherein Y and Z each is independently N or C; ring A is a carbocyclic group or a heterocyclic group; ring B is a heterocyclic group containing at least one nitrogen atom; R is a hydrogen atom, a s

Dihydrobenzoxazines and Tetrahydroquinoxalines by a Tandem Reduction-Reductive Amination Reaction

A tandem reduction-reductive amination reaction has been applied to the synthesis of 3,4-dihydro-2H-1,4-benzoxazines and 1-acetyl-1,2,3,4-tetrahydroquinoxalines. The nitroketones required for the benzoxazine ring closures were prepared by (A) alkylation of the anion derived from 2-nitrophenol with an allylic halide or (B) nucleophilic aromatic substitution of an allylic alkoxide on 2-fluoro-1-nitrobenzene followed by ozonolysis. Precursors for the quinoxalines were prepared by alkylation of the anion of 2-nitroacetanilide with an allylic halide followed by ozonolysis. Catalytic hydrogenation of the nitroketones using 5% palladium-on-carbon in methanol then gave the target heterocycles by a reduction-reductive amination sequence. The N-methyl derivatives for both ring systems were easily prepared by adding 5-10 equivalents of aqueous formaldehyde prior to the reduction. The dihydrobenzoxazines were isolated in high yield following purification by chromatographic methods; tetrahydroquinoxalines were isolated in a similar manner and possessed differentiated functionality on the two nitrogens.

Novel exploration of the SNAr reaction

Propargylic, allylic and benzylic alcohols prove to be fairly successful as activated nucleophiles, under mild conditions for the SNAr reaction.

Potent inhibitors of Acyl-CoA:cholesterol acyltransferase. 2. Structure- activity relationships of novel N-(2,2-dimethyl-2,3-dihydrobenzofuran-7- yl)amides

Novel N-(2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)amide derivatives 1 were synthesized and tested for their ability to inhibit rabbit small intestinal ACAT (acyl-CoA:cholesterol acyltransferase) and lower serum total cholesterol in cholesterol-fed rats. Among the synthesized compounds, N-(2,2,4,6- tetramethyl-2,3-dihydrobenzofuran-7-yl)amide derivatives showed potent ACAT inhibitory activity. The synthesis and structure-activity relationships of these compounds are described. A methyl group at position 6 of the 2,3- dihydrobenzofuran moiety was important for potent ACAT inhibitory activity. In the series of N-(2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-7-yl)amides, lipophilicity of the acyl moiety was necessary for the potent ACAT inhibitory activity. The highly lipophilic acid amides N-(2,2,4,6-tetramethyl-2,3- dihydrobenzofuran-7-yl)-2,2-dimethyldodecanamide (10) and 6-(4- chlorophenoxy)-N-(2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-7-yl)-2,2- dimethyloctanamide (50) showed potent activity. Introduction of a dimethylamino group at position 5 of the 2,3-dihydrobenzofuran moiety resulted in highly potent activity. The most potent compound, N-[5- (dimethylamino)-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-7-yl]-2,2- dimethyldodecanamide (13, TEI-6620), showed highly potent ACAT inhibitory activity (rabbit small intestine IC50 = 0.020 μM, rabbit liver IC50 = 0.009 μM), foam cell formation inhibitory activity (rat peritoneal macrophage IC50 = 0.030 μM), extremely potent serum cholesterol-lowering activity in cholesterol-fed rats (71% at a dose of 0.3 mg/kg/day po), and good bioavailability in fed dogs (C(max) = 2.68 μg/mL at 1 h, 10 mg/kg po).