19615-50-0

Usage

InChI:InChI=1/C10H12O4/c1-4-13-10(12)8-5-9(6(2)11)14-7(8)3/h5H,4H2,1-3H3

Upstream product

• 122132-62-1 5-Eth-(E)-ylidene-2-methyl-4,5-dihydro-furan-3-carboxylic acid ethyl ester 
• 130533-19-6 5-(1-hydroperoxyethyl)-3-ethoxycarbonyl-2-methylfuran 
• 23012-25-1 2,4-dimethyl-5-acetyloxazole 
• 623-47-2 propynoic acid ethyl ester 
• 79495-05-9 4-Butyl-2-ethanoyl-5-methyloxazole 
• 122132-65-4 2-methyl-3-ethoxycarbonyl-5-ethylidene-4,5-dihydrofuran 
• 224424-74-2 ethyl 5-acetyl-2-methyl-4,5-dihydrofuran-3-carboxylate 
• 141-97-9 ethyl acetoacetate 

Relevant academic research and scientific papers

Domino Michael-O-alkylation reaction: One-pot synthesis of 2,4-diacylhydrofuran derivatives and its application to antitumor naphthofuran synthesis

The one-pot synthesis of 2,4-diacylhydrofuran derivatives and its applications to antitumor napthofuran synthesis was discussed. It was found that the reaction of 1,3-dicarbonyl compounds with α-halo-α,β-unsaturated carbonyl compounds afforded 2,4-diacyldihydrofuran derivatives in the presence of DBU in THF. The analysis showed that the applications of the protocol enabled short-step synthesis of antitumor napthofuran natural products.

Asymmetric synthesis with the enzyme Coprinus peroxidase: Kinetic resolution of chiral hydroperoxides and enantioselective sulfoxidation

The enzyme Coprinus peroxidase (CiP) was employed for the kinetic resolution of racemic hydroperoxides 1 and the asymmetric sulfoxidation of prochiral sulfides 4. Eleven hydroperoxides 1a-k were reduced by CiP and guaiacol as reductant under conditions of kinetic resolution with enantioselectivities of up to >98% for the (S)-hydroperoxide 1 and 90% for the (R)-alcohol 2. In the absence of a reductant, the hydroperoxide 1a afforded with CiP enantiomerically enriched hydroperoxide la (ee up to 54%) and alcohol 2a (ee up to 40%), as well as ketone 3a (which is also formed simultaneously in all other reactions) and molecular oxygen. Catalase activity was established for CiP with hydrogen peroxide. When aryl alkyl sulfides 4 were used as oxygen acceptors, three products, sulfoxides 5, alcohols 2, and hydroperoxides 1, were obtained, all in enantiomerically enriched form. The highest ee value (89%) was achieved for the sulfoxide derived from naphthyl methyl sulfide (4f). Thus, CiP may be utilized for the asymmetric synthesis of optically active hydroperoxides 1, alcohols 2, and sulfoxides 5.

Tandem nucleophilic reaction leading to hydrofurans: Application to one- pot synthesis of antitumor naphthofuran natural product

The reaction of enolates of 1,3-dicarbonyl compounds (1) with 3,4- dibromo-2-butanone (2) afforded hydrofuran derivatives (4) or (5) in the presence of DBU in THF and the reaction was applied to the one-pot synthesis of antitumor naphthofuran products (29).

Chemical, photochemical and enzymatic approach to furylhydroperoxides

Furylhydroperoxides are accessible by three different methodologies. In the enzymatic approach, lypoxygenase is employed on non lipid-like substrates. Transition metal catalyzed epoxidation of allylic alcohols is strongly dependent on the structure of the involved hydroperoxide.

A NEW APPROACH TO POLYFUNCTIONAL FURYLCARBINOLS

3-Alkoxycarbonyl- and 3-acyl-5-furylcarbinols 3 are obtained by a simple and mild procedure based on photo-oxygenation of 5-alkylidene-4,5-dihydrofurans 1 and reduction of the resulting hydroperoxides 2.

Lipoxygenase-catalyzed dehydration of furylhydroperoxides

3-alkoxycarbonyl-5(1-hydroperoxyalkyl)-furans 1 are changed into the corresponding 5-acyl and 5-formyl derivatives 2 by a lipoxygenase-catalyzed process. The conversion shows to proceed in enantioselective way leading to chiral furylhydroperoxides and furylalcohols. 3-alkoxycarbonyl-5(1-hydroperoxyalkyl)-furans 1 are changed into the corresponding 5-acyl and 5-formyl derivatives 2 by a lipoxygenase-catalyzed process.

REACTIONS OF OXAZOLES WITH ACETYLENE DERIVATIVES. PART III. REACTIONS OF TRISUBSTITUTED OXAZOLE DERIVATIVES WITH ETHYL PROPIOLATE

Diene reactions between dimethyloxazoles containing an electron accepting group in positions 2 or 5 with ethyl propiolate were investigated.The formation of both possible, isomeric furan derivatives was stated in the case of all these reactions.The ratio of both products depends on the kind of the electron accepting group and does not depend on the places of methyl and electron accepting groups in positions 2 and 5 in the oxazole.