200404-35-9

Usage

Uses

Used in Pharmaceutical Industry:
3-OXO-3-M-TOLYL-PROPIONIC ACID METHYL ESTER is used as an intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new medications.
Used in Flavoring and Food Industry:
3-OXO-3-M-TOLYL-PROPIONIC ACID METHYL ESTER is used as a flavoring agent in food and beverages, enhancing the taste and aroma due to its fruity odor.
Used in Fragrance Industry:
3-OXO-3-M-TOLYL-PROPIONIC ACID METHYL ESTER is used in the production of perfumes and colognes, adding a pleasant aroma to these products.

Upstream product

• 616-38-6 carbonic acid dimethyl ester 
• 585-74-0 3-Methylacetophenone 

Downstream Products

• 22899-60-1 3-amino-4-(m-tolyl)-1,2,5-oxadiazole 
• 1372793-71-9 trans-methyl 3-(methoxyimino)-3-(m-tolyl)propanoate 

Relevant academic research and scientific papers

Cu-Catalyzed Synthesis of Benzoxazole with Phenol and Cyclic Oxime

A Cu-catalyzed straightforward synthesis of benzoxazoles from free phenols and cyclic oxime esters is reported. The mild reaction conditions tolerate various electron-withdrawing and electron-donating functional groups on both substrates, affording benzoxazoles in moderate to good yields. With this protocol, large-scale syntheses of Ezutromid and Flunoxaprofe in one or two steps are demonstrated. A catalytic mechanism, which includes Cu-catalyzed amination via inner-sphere electron transfer and consequent annulation, is proposed.

Enantioselective decarboxylative Mannich reaction of β-keto acids withC-alkynylN-BocN,O-acetals: access to chiral β-keto propargylamines

The chiral keto-substituted propargylamines are an essential class of multifunctional compounds in the field of organic and pharmaceutical synthesis and have attracted considerable attention, but the related synthetic approaches remain limited. Therefore, a concise and efficient method for the enantioselective synthesis of β-keto propargylaminesviachiral phosphoric acid-catalyzed asymmetric Mannich reaction between β-keto acids andC-alkynylN-BocN,O-acetals as easily availableC-alkynyl imine precursors has been demonstrated here, affording a broad scope of β-ketoN-Boc-propargylamines in high yields (up to 97%) with generally high enantioselectivities (up to 97?:?3 er).

1-cyclohexylpyrazolone carboxylesterase 1 inhibitor as well as preparation and application thereof

The invention discloses a 1-cyclohexylpyrazolone carboxylesterase 1 inhibitor as well as preparation and application thereof. The structural general formula of the carboxylesterase 1 inhibitor is shown in the specification, wherein R1 and R2 are any one of phenyl, benzyl, 2-methylphenyl, 4-methylphenyl, 4-methylbenzyl and 2-naphthyl respectively. The IC50 for preparing hCES1A reaches 50 nanomoles,and the ratio of the IC50 for inhibiting hCES2A to the IC50 for inhibiting hCES1A can reach 252 times. The inhibitor can improve the oral bioavailability of carboxylic ester exogenous prodrugs by inhibiting the activity of human carboxylesterase subtype 1, or can be used as a synergist of clopidogrel, and can also effectively inhibit the generation of fat cell lipid droplets induced by a mouse preadipose 3T3-L1 cell line. According to the carboxylesterase 1 inhibitor, the raw materials are easy to obtain, the cost is low, the synthesis process is simple, and the yield is high; the inhibitionactivity is high, the selectivity is good, and the application prospect is great.

Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds

Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds provides a simple and atom-economical approach toward enamides and isoquinolones. This paper reports two catalyst systems for these transformations which employ iron(ii) complexes [Fe(dpbz)]Br2 (dpbz = 1,2-bis(diphenylphosphino)benzene) and FeBr2/Et3N, respectively. [Fe(dpbz)]Br2 was found to be highly effective at converting 2-azido-2,3-dihydro-1H-inden-1-ones to isoquinolones. The reagent combination of FeBr2/Et3N, on the other hand, exhibited a broader catalytic scope, owing to the beneficial effect of Et3N. This latter catalyst system enables 2-azido-2-methyl-1,3-dicarbonyl compounds to be converted to the corresponding enamides under mild conditions in good yields.

Rhodium-Catalyzed Enantioconvergent Isomerization of Homoallylic and Bishomoallylic Secondary Alcohols

We present herein an unprecedented enantioselective isomerization of homoallylic and bishomoallylic secondary alcohols, catalyzed by a commercially available rhodium-complex and a base. This catalytic redox-neutral process provides an effective access to chiral ketones in high efficiency and enantioselectivity, without the use of any stoichiometric reagent or generation of any waste. For the reaction of homoallylic alcohols, this system achieved not only a stereoconvergent access to chiral ketones bearing a β-stereocenter (up to 95%, 86% ee) but also a concomitant oxidative kinetic resolution of the alcohol substrates (S > 20). In the case of bishomoallylic alcohols, an intriguing ligand-induced divergent reactivity was observed. A terminal-to-internal alkene isomerization promoted by Rh/L7 followed by redox isomerization using Rh/BINAP system produced chiral ketones bearing a γ-stereocenter with high yield and enantioselectivity. Mechanistic studies provided strong support for the redox-isomerization pathway with chain walking of the key alkyl-Rh intermediate.

SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes

Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).

Palladium-Catalyzed Enantioselective Narasaka–Heck Reaction/Direct C?H Alkylation of Arenes: Iminoarylation of Alkenes

A palladium-catalyzed reaction of γ,δ-unsaturated oxime esters with oxadiazoles afforded dihydropyrroles in good to excellent yields through an intramolecular iminopalladation/intermolecular direct heteroarene C?H alkylation cascade. This unprecedented iminoarylation of alkenes was subsequently realized in an enantioselective manner in the presence of a chiral bidentate phosphine ligand (Synphos).

Nickel-catalyzed enantioselective hydrogenation of β-(acylamino)acrylates: Synthesis of chiral β-amino acid derivatives

The nickel-catalyzed asymmetric hydrogenation of β-(acylamino)acrylates has been developed, affording chiral β-amino acid derivatives with excellent yields (95-99% yield) and enantioselectivities (97-99% ee). With the Ni-Binapine system, high enantioselectivities (98-99% ee) have also been obtained in the hydrogenation of Z/E isomeric mixtures of β-alkyl and β-aryl β-(acylamino)acrylates. The synthesis of chiral β-amino acid derivatives on a gram scale has also been achieved with 0.2 mol % catalyst loading.

Copper-Catalysed Decarboxylative Trifluoromethylation of β-Ketoacids

An efficient method for Cu-catalyzed decarboxylative trifluoromethylation of β-ketoacids to achieve α-trifluoromethyl ketones was developed. A wide variety of synthetically useful α-trifluoromethyl ketones were obtained in modest to good yields under mild reaction conditions. The present method also exhibits good functional-group compatibility.

SUBSTITUTED OXAZOLE- AND THIAZOLE-BASED CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS II

The invention relates to oxazole and thiazole-based carboxamide and urea derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.