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Revisiting the Hinsberg reaction: Facile and expeditious synthesis of 3-substituted quinoxalin-2(1H)-ones under catalyst-free conditions in water

Substituted benzene-1,2-diamine reacted with various alpha-keto esters at 50 under mild conditions for 15 min using H2O as reaction medium, providing a variety of 3-substituted quinoxalinone derivatives in excellent yields. The reaction was instantaneous, and products were isolated by simple filtration.

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Tetrahydrofuran – Wikipedia,
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Fundamental insights into the enantioselectivity of hydrogenations on cinchona-modified platinum and palladium

The influence of the configuration at the C8 and C9 positions of cinchona alkaloids was investigated by comparing the efficiency of cinchonidine, cinchonine, and 9-epi-cinchonidine as chiral modifiers. In the hydrogenation of ketones (methyl benzoylformate, ketopantolactone, methylglyoxal dimethylacetal, 2,2,2-trifluoroacetophenone) on Pt, a change in the configuration at C9 did not affect the absolute configuration of the main products; however, the ees and rates dropped significantly. In the hydrogenation of alpha-functionalized olefins (E-2-methyl-2-hexenoic acid, 2-phenylcinnamic acid, and 4-methoxy-6-methyl-2H-pyran-2-one) on Pd, replacement of cinchonidine or cinchonine by epi-cinchonidine diminished the rates and almost eliminated the enantioselection, indicating that a subtle combination of C8 and C9 configurations is required on Pd. DFT calculations of the adsorption of the modifiers and the nonlinear behavior of modifier mixtures revealed that the lower reaction rates observed for 9-epi-cinchonidine-modified surfaces cannot be related to different adsorption strength of this modifier. Additionally, substrate-modifier docking interactions are presented.

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Tetrahydrofuran – Wikipedia,
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Convenient fluoride-mediated reactions of lactones with silyl ketene acetals

Aldolisation reactions of silyl ketene acetals with lactone carbonyls can be performed under very mild conditions in good yields in the presence of 5-10 mol-% of TASF.

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13031-04-4, Name is 4,4-Dimethyldihydrofuran-2,3-dione, belongs to Tetrahydrofurans compound, is a common compound. Application In Synthesis of 4,4-Dimethyldihydrofuran-2,3-dioneIn an article, once mentioned the new application about 13031-04-4.

REACTION OF TRIPHENYLPHOSPHINE-CARBON TETRAHALIDE REAGENT WITH alpha-KETO-gamma-LACTONE

Triphenylphosphine-carbon tetrahalide reagent reacts with 4,4-dimethyloxolan-2,3-dione to afford two dihalomethyleneoxolanes, 8 and 9.The major reaction course can be changed by the addition order of the reagents.Reaction mechanisms are discussed.

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Characterization of volatile compounds in four different rhododendron flowers by GC_GC-QTOFMS

Volatile compounds in flowers of Rhododendron delavayi, R. agastum, R. annae, and R. irroratum were analyzed using comprehensive two-dimensional gas chromatography-mass spectrometry (GC_GC) coupled with high-resolution quadrupole time-of-flight mass spectrometry (QTOFMS). A significantly increased number of compounds was separated by GC_GC compared to conventional one-dimensionalGC(1DGC), allowing more comprehensive understanding of the volatile composition of Rhododendron flowers. In total, 129 volatile compounds were detected and quantified. Among them, hexanal, limonene, benzeneacetaldehyde, 2-nonen-1-ol, phenylethyl alcohol, citronellal, isopulegol, 3,5-dimethoxytoluene, and pyridine are the main compounds with different content levels in all flower samples. 1,2,3-trimethoxy-5-methyl-benzene exhibits significantly higher content in R. irroratum compared to in the other three species, while isopulegol is only found in R. irroratum and R. agastum.

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A substrate-based folding process incorporating chemodifferentiating ABB’ three-component reactions of terminal alkynoates and 1,2-dicarbonyl compounds: A skeletal-diversity-oriented synthetic manifold

A novel three-component reaction (3CR)-based folding process that is able to generate complexity and skeletal diversity is described. The process utilizes chemodifferentiating organ-ocatalyzed ABB’ 3CRs of a terminal conjugated alkynoate (building block) with alpha-dicarbonyl compounds (diversity-generating blocks) to generate an array of different molecular topologies (gamma-lactones, linear propargylic enol ethers, or 1,3-dioxolane rings). Amides and esters behave as efficient reactivi ty-encoding elements (sigma) of the attached keto functionality. Three chemical properties govern the chemical outcome of this folding process: acidity, nucleophilicity (of the catalyst), and carbonyl electrophilicity. Overall, this substrate-based folding process gener ates three different molecular architectures from the same modular functionalities (ketones) and under the same reaction conditions (methyl propiolate and tertiary amine). In addition, and very importantly for combinatorial applications, all of the products share a common reactive functionality that allows them to be collective substrates for a subsequent diversity-generating process.

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Tetrahydrofuran – Wikipedia,
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Preparation of 4,4-dimethyltetrahydrofuran-2,3-dione

4,4-Dimethyltetrahydrofuran-2,3-dione is prepared by reacting a dimethylpyruvate (II) with formaldehyde or a formaldehyde donor at 80-150 C.

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Extracurricular laboratory:new discovery of 4,4-Dimethyldihydrofuran-2,3-dione

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Cationic rhodium(I)/H8-binap complex catalyzed [2+2+2] cycloadditions of 1,6- And 1,7-diynes with carbonyl compounds

We have established that a cationic rhodium(I)/H8-binap complex catalyzes [2+2+2] cycloadditions of a variety of 1,6and 1,7-diynes with both electron-deficient and electron-rich carbonyl compounds, leading to dienones in high yield under mild reaction conditions. In the reactions with acyl phosphonates, the reactivity of 1,6- and 1,7-diynes was highly dependent on their own structures. The addition of chelating diethyl oxalate effectively promoted the [2+2+2] cycloadditions involving acyl phosphonates, presumably due to the equilibrium formation of the desired 1:1 rhodium complex of the diyne and the acyl phosphonate by facile ligand exchange between the diyne and weakly coordinated diethyl oxalate. In the reactions involving bifunctional carbonyl compounds or unsymmetrical 1,6-diynes, high chemo- or regioselectivities were observed. Wiley-VCH Verlag GmbH & Co. KGaA.

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Hydrogenation of alpha-ketoesters and ketopantolactone on rhodium modified by cinchona and isocinchona alkaloids

Various Rh catalysts and cinchona-type modifiers were tested in the hydrogenation of ethyl pyruvate, ethyl 3-methyl-2-oxobutyrate, and ketopantolactone. The experiments were completed with the study of the nonlinear behavior of modifier mixtures, and UV and NMR analysis of hydrogenation of the modifiers. From this study, beta-isocinchonine emerged as an outstanding modifier of Rh/Al2O3 that gave up to 68% ee in the hydrogenation of ketopantolactone to (R)-pantolactone in toluene, at full conversion and without the formation of any detectable byproducts. Careful prereduction of the catalyst at elevated temperature is critical to achieve good enantioselectivity. The loss of ee, or even the formation of the opposite enantiomer in small excess, in protic solvents is attributed to the formation of solvent-substrate and solvent-modifier complexes that disturb the enantioselection on cinchona-modified Rh. In the weakly interacting solvent toluene, only a few ppm of beta-isocinchonine related to ketopantolactone was sufficient to induce enantioselection. This unique feature of the conformationally rigid isocinchona alkaloid is attributed to the stronger adsorption on Rh and weaker adsorption on Al2O3, and to the higher resistance against hydrogenation of its quinoline ring “anchoring moiety” compared with the corresponding values of cinchonine and cinchonidine.

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Method for producing carbonyl compound

[summary][PROBLEM TO BE SOLVED]: To provide a method for effectively producing carbonyl compound from alcohol using a ruthenium compound as an oxidation catalyst which can apply to various alcoholic compounds as starting materials, and to provide a method for effectively producing the carbonyl compound in high yield with decomposing neither the alcohol nor the produced carbonyl compound.[SOLUTION]: The method for producing carbonyl compound comprises the oxidative reaction process of alcohol using N-haloamide compound or N-haloimide compound in the presence of ruthenium compound of catalytic amount in the solvent containing organic solvent not substantially oxidized with the ruthenium compound The solvent used is solvent containing organic solvents other than the carboxylic acid; mixed solvent of pH5-14 containing organic solvent and water; or organic solvent containing base.

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Tetrahydrofuran – Wikipedia,
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