6309-18-8

Usage

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

Upstream product

• 74-90-8 hydrogen cyanide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 151-50-8 potassium cyanide 
• 613-90-1 benzoyl cyanide 
• 95392-01-1 2-(3,4-dimethoxyphenyl)-2-((trimethylsilyl)oxy)acetonitrile 
• 2033-89-8 3,4-dimethoxyphenol 
• 7677-24-9 trimethylsilyl cyanide 
• 143-33-9 sodium cyanide 
• 68413-92-3 sodium (3,4-dimethoxyphenyl)(hydroxy)methanesulfonate 

Downstream Products

• 102-32-9 3,4-dihydroxyphenylacetate 
• 95392-01-1 2-(3,4-dimethoxyphenyl)-2-((trimethylsilyl)oxy)acetonitrile 
• 125237-18-5 p,p'-bis(α-cyano(3,4-dimethoxyphenyl)methylhydrazinocarbonylmethoxy)diphenyl sulphone 
• 6924-15-8 2-amino-1-(3,4-dimethoxy-phenyl)-ethanol 
• 28750-77-8 α-chloro-3,4-dimetoxybenzeneacetonitrile 
• 94782-89-5 1'-cyano-3,4-dimethoxybenzylamine 
• 65961-86-6 (3,4-dimethoxy-phenyl)-glyoxylonitrile 
• 95392-05-5 2-(3,4-dimethoxyphenyl)-2-fluoroacetonitrile 
• 143378-36-3 2-(3,4-dimethoxyphenyl)-2-(tert-butyldiphenylsilyloxy)acetonitrile 
• 158705-95-4 (3S,4R)-(+)-6,7-dimethoxy-4-hydroxy-1-methyl-3-phenyl-3,4-dihydroisoquinoline 
• 25932-34-7 6,7-dimethoxy-1-(4-nitrobenzyl)isoquinoline 
• 83633-13-0 4-[(6,7-dimethoxy-1-isoquinolinyl)methyl]benzenamine 
• 83633-37-8 N-<2-hydroxy-2-(3,4-dimethoxyphenyl)ethyl>-4-nitrobenzeneacetamide 
• 83633-23-2 N-(2-chloroethyl)-4-[(6,7-dimethoxy-1-isoquinolinyl)methyl]benzenamine 

Relevant academic research and scientific papers

One-pot access to 2-amino-3-arylbenzofurans: Direct entry to polyheterocyclic chemical space

As a means to make new benzofuran-embedded polycyclic structures, we established two efficient one-pot sequential coupling routes to 2-amino-3-arylbenzofurans and 2-amino-3-arylnaphtho[2,1-b]furans. Further ring formation (six- and seven-membered rings) with the resulting amine moiety at the C2 position of benzofurans was realized, leading to further expansion of benzofuran-based chemical space.

Chiral solvating agents for cyanohydrins and carboxylic acids

We have shown that a structure as simple as an ion pair of (R)- or (S)-mandelate and dimethylamminopyridinium ions possesses structural features that are sufficient for NMR enantiodiscrimination of cyanohydrins. Moreover, 1H NMR data of cyanohydrins of known configuration obtained in the presence of the mandelate-dimethylaminopyridinium ion pair point to the existence of a correlation between chemical shifts and absolute configuration of cyanohydrins. Mandelate-DMAPH+ ion pair and mandelonitrile form a 1:1 complex with an association constant of 338 M-1 (ΔG 0, -3.4 kcal/mol) for the (R)-mandelonitrile/(R)-mandelate-DMAPH + and 139 M-1 (ΔG0, -2.9 kcal/mol) for the (R)-mandelonitrile/(S)-mandelate-DMAPH+ complex. To understand the origin of enantiodiscrimination, the geometry optimization and energy minimization of the models of ternary complexes of (S)-mandelonitrile/(R)- mandelate/DMAPH+ and (S)-mandelonitrile/(S)-mandelate/DMAPH + complexes was performed using DFT methodology (B3LYP) with the 6-31+G(d) basis set in Gaussian 3.0. Further, analysis of optimized molecular model obtained from theoretical studies suggested that (i) DMAP may be replaced with other amines, (ii) the hydroxyl group of mandelic acid is not necessary for stabilization of ternary complex and may be replaced with other groups such as methyl, (iii) the ion pair should form a stable ternary complex with any hydrogen-bond donor, provided its OH bond is sufficiently polarized, and (iv) α-H of racemic mandelic acid should also get resolved with optically pure mandelonitrile. These inferences were experimentally verified, which not only validated the proposed model but also led to development of a new chiral solvating agent for determination of ee of carboxylic acids and absolute configuration of aryl but not alkyl carboxylic acids.

2-(ARYLOXY)ACETAMIDE FACTOR VIIA INHIBITORS USEFUL AS ANTICOAGULANTS

The present invention relates generally to novel 2-(aryloxy)acetamides of Formula (I) or stereoisomers, tautomers, pharmaceutically acceptable salts, solvates, or prodrugs thereof, wherein the variables W, Y, Z, R7, R8, and R9 are as defined herein. These compounds are selective inhibitors of the serine protease coagulation factor VIIa which can be used as medicaments.

Application of crude preparations of leaves from food plants for the formation of cyanohydrins with high enantiomeric excesses

Crude preparations obtained from mamey (Pouteria sapota), capulin (Prunus serotina var. capulli) and peach (Prunus persica) leaves were used to catalyze the enantioselective addition of HCN to a variety of aldehydes. The corresponding cyanohydrins were obtained with high levels of enantioselectivity, comparable with those obtained with other catalysts used for the same purpose.

A new (R)-hydroxynitrile lyase from Prunus mume: Asymmetric synthesis of cyanohydrins

A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC based enantioselective assay technique was developed for the enzyme, which promotes the addition of KCN to benzaldehyde in a buffered solution (pH=4.5).

Ruthenium-Catalyzed Oxidations of Alcohols

A combination of low-valent ruthenium complexes and peroxides such as t-BuOOH and peracids serves as efficient catalytic systems for the oxidation of aromatic and aliphatic hydroxy compounds. The utility of these methods was demonstrated by the synthesis of acyl cyanides which are versatile synthetic intermediates. The principle of the catalytic oxidations with peracids lead to the novel and efficient method for aerobic oxidation of alcohols in the presence of aldehydes. This reaction is of importance in synthetic and large scale industrial processes and from environmental points of view. The present principle will provide new chemistry of oxidative transformations of various industrially important functional materials.

Reductive Coupling of Benzoyl Cyanide and Carbonyl Compounds by Aqueous Ti(III) Ions. A New Convenient and Selective Access to the Less Stable Mixed Benzoins

The reactive species formed by the Ti(III) ion reduction of benzoyl cyanide (1) adds to the C-atom of carbonyl compounds 2 under simple experimental conditions.The intermediate 1,2-diols 3 are smoothly converted, without isolation, into the less thermodynamically stable mixed benzoins 4, which are not accessible by the classical benzoin condensation.The possible mechanisms involved in the reaction are discussed.

Synthesis and antimicrobial activity of some heterocyclic compounds

Condensation of 2-phenyl-3-(4-benzoyl hydride)-1,3-quinazolin-4(4H)-one (1) with various aldehydes gives 2-phenyl-3-(4-arylidene-benzoylhydrazide)-1,3-quinazolin-4(4H)-one (II), which on cycloaddition with mercaptoacetic acid yield 4-thiazolidinones (IIIa-o).Compound (I) on treatment with aromatic cyanohydrines and aryl isothiocyanates gives α-carbohydrazino nitriles of (IVa-m) and thiosemicarbazides (Va-l) respectively.The structures of III-V have been elucidated on the basis of their elemental analysis and spectral data.These compounds exhibit moderate to goodantibacterial and tuberculostatic activities.