3194-15-8Relevant articles and documents
Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal
Zhan, Huan,Cui, Heping,Yu, Junhe,Hayat, Khizar,Wu, Xian,Zhang, Xiaoming,Ho, Chi-Tang
, (2021/09/28)
The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r
Method for preparing 2-acyl furan
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Paragraph 0024; 0027, (2019/12/25)
The invention relates to a method for preparing 2-acyl furan. The method is characterized by comprising the following steps: (1) controlling the temperature to -10-40 DEG C, and adding 70-98% of a water phase or 10-90% of a mixed liquid of the water phase and an organic phase, 0.0001-2.0% of an osmium compound and 0.001-5.0% of an amine compound into a reaction container so as to obtain a reactionliquid; (2) feeding the reaction liquid into a sealed reactor, and performing gas exchange to provide an aerobic environment for reactions; (3) adding 1-(2-furyl)-1-alkyl methanol into the sealed reactor, and controlling the pressure to 0-20MPa and the temperature to 0-200 DEG C for 1-74 hours; and (4) after the reaction is stopped, performing cooling to the room temperature, performing pressurerelease to the barometric pressure, adding sodium hydrogen sulfate and acetic acid, performing extraction, and performing organic phase vacuum distillation refining, so as to obtain a 2-acyl furan product. The method has the advantages that technical and economical defects of a conventional synthesis route can be avoided, process procedures can be reduced, consumption and emission can be reduced,the energy consumption and the cost can be lowered, and the method is applicable to capacity increase industrial production.
Manganese PNP-pincer catalyzed isomerization of allylic/homo-allylic alcohols to ketones-activity, selectivity, efficiency
Xia, Tian,Spiegelberg, Brian,Wei, Zhihong,Jiao, Haijun,Tin, Sergey,Hinze, Sandra,De Vries, Johannes G.
, p. 6327 - 6334 (2019/11/20)
We report the first manganese catalyzed isomerization of allylic alcohols to produce the corresponding carbonyl compounds. The ligand plays a decisive role in the efficiency of this reaction. Very high conversions could be obtained using a solvent-free reaction system. A detailed DFT study reveals a self-dehydrogenation/hydrogenation reaction mechanism which was verified by the isolation of the α,β-unsaturated ketone as intermediate and a deuterium labeling experiment. It also provided a rationale for the observed selectivity and the higher efficiency of phenyl over isopropyl substitution.
Additive-Free Isomerization of Allylic Alcohols to Ketones with a Cobalt PNP Pincer Catalyst
Spiegelberg, Brian,Dell'Acqua, Andrea,Xia, Tian,Spannenberg, Anke,Tin, Sergey,Hinze, Sandra,de Vries, Johannes G.
supporting information, p. 7820 - 7825 (2019/05/22)
Catalytic isomerization of allylic alcohols in ethanol as a green solvent was achieved by using air and moisture stable cobalt (II) complexes in the absence of any additives. Under mild conditions, the cobalt PNP pincer complex substituted with phenyl groups on the phosphorus atoms appeared to be the most active. High rates were obtained at 120 °C, even though the addition of one equivalent of base increases the speed of the reaction drastically. Although some evidence was obtained supporting a dehydrogenation–hydrogenation mechanism, it was proven that this is not the major mechanism. Instead, the cobalt hydride complex formed by dehydrogenation of ethanol is capable of double-bond isomerization through alkene insertion–elimination.
Ligand-Controlled Chemoselective C(acyl)-O Bond vs C(aryl)-C Bond Activation of Aromatic Esters in Nickel Catalyzed C(sp2)-C(sp3) Cross-Couplings
Chatupheeraphat, Adisak,Liao, Hsuan-Hung,Srimontree, Watchara,Guo, Lin,Minenkov, Yury,Poater, Albert,Cavallo, Luigi,Rueping, Magnus
supporting information, p. 3724 - 3735 (2018/03/21)
A ligand-controlled and site-selective nickel catalyzed Suzuki-Miyaura cross-coupling reaction with aromatic esters and alkyl organoboron reagents as coupling partners was developed. This methodology provides a facile route for C(sp2)-C(sp3) bond formation in a straightforward fashion by successful suppression of the undesired β-hydride elimination process. By simply switching the phosphorus ligand, the ester substrates are converted into the alkylated arenes and ketone products, respectively. The utility of this newly developed protocol was demonstrated by its wide substrate scope, broad functional group tolerance and application in the synthesis of key intermediates for the synthesis of bioactive compounds. DFT studies on the oxidative addition step helped rationalizing this intriguing reaction chemoselectivity: whereas nickel complexes with bidentate ligands favor the C(aryl)-C bond cleavage in the oxidative addition step leading to the alkylated product via a decarbonylative process, nickel complexes with monodentate phosphorus ligands favor activation of the C(acyl)-O bond, which later generates the ketone product.
Isomerization of Allylic Alcohols to Ketones Catalyzed by Well-Defined Iron PNP Pincer Catalysts
Xia, Tian,Wei, Zhihong,Spiegelberg, Brian,Jiao, Haijun,Hinze, Sandra,de Vries, Johannes G.
supporting information, p. 4043 - 4049 (2018/01/27)
[Fe(PNP)(CO)HCl] (PNP=di-(2-diisopropylphosphanyl-ethyl)amine), activated in situ with KOtBu, is a highly active catalyst for the isomerization of allylic alcohols to ketones without an external hydrogen supply. High reaction rates were obtained at 80 °C, but the catalyst is also sufficiently active at room temperature with most substrates. The reaction follows a self-hydrogen-borrowing mechanism, as verified by DFT calculations. An alternative isomerization through alkene insertion and β-hydride elimination could be excluded on the basis of a much higher barrier. In alcoholic solvents, the ketone product is further reduced to the saturated alcohol.
2-Methyl-3-aryloxy-3-heteroarylpropylamine compounds and application
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Paragraph 0065; 0066, (2017/06/28)
The invention relates to 2-methyl-3-aryloxy-3-heteroarylpropylamine compounds and their pharmaceutical application. It is discovered via experiments that these compounds are KCNQ2/3 channel blockers, having good anti-depression activity, capable of improving cognitive function and having low acute toxicity.
Direct conversion of allyl arenes to aryl ethylketones via a TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes
Zhao, Jinwu,Liu, Li,Xiang, Shijian,Liu, Qiang,Chen, Huoji
supporting information, p. 5613 - 5616 (2015/05/27)
A TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes was developed. This methodology provides a new efficient and simple route for conversion of a range of allyl arenes directly into aryl ethylketones in good yields with high chemoselectivity.
Catalytic isomerization of allylic alcohols promoted by complexes [RuCl2(η6-arene)(PTA-Me)] under homogeneous conditions and supported on Montmorillonite K-10
Menéndez-Rodríguez, Lucía,Crochet, Pascale,Cadierno, Victorio
, p. 390 - 399 (2013/02/21)
The mononuclear arene-ruthenium(II) derivatives [RuCl2(η 6-arene)(PTA-Me)] (arene = C6H6 (3a), p-cymene (3b), 1,3,5-C6H3Me3 (3c), C6Me 6 (3d)), containing the ionic phosphine ligand 1-methyl-3,5-diaza-1- azonia-7-phosphaadamantane chloride (PTA-Me), have been synthesized and fully characterized. These complexes were evaluated as potential catalysts for the redox isomerization of allylic alcohols. Among them, best results in terms of activity were obtained with complex [RuCl2(η6-C 6H6)(PTA-Me)] (3a) which, in combination with K 2CO3 (2.5 equiv. per Ru), was able to selectively isomerize a number of allylic alcohols RCH(OH)CHCH2 (R = H, aryl, alkyl or heteroaryl group) into the corresponding carbonyl compounds RC(O)CH2CH3 in refluxing THF (TOF values up to 800 h -1). Complex [RuCl2(η6-C6H 6)(PTA-Me)] (3a) was adsorbed onto the Montmorillonite K-10 clay, and the resulting solid proved also active in the isomerization of the model substrate 1-octen-3-ol. In addition, it could be easily separated from the reaction media by simple filtration and reused several times (up to 11 consecutive runs) with retention of its efficiency.
C5′-alkyl substitution effects on digitoxigenin α-l-glycoside cancer cytotoxicity
Wang, Hua-Yu Leo,Wu, Bulan,Zhang, Qi,Kang, Sang-Woo,Rojanasakul, Yon,O'Doherty, George A.
scheme or table, p. 259 - 263 (2011/06/16)
A highly regio- and stereoselective asymmetric synthesis of various C5′-alkyl side chains of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation with postglycosylated dihydroxylation or diimide reduction. The C5′-methyl group in both α-l-rhamnose and α-l-amicetose digitoxin analogues displayed a steric directed apoptosis induction and tumor growth inhibition against nonsmall cell human lung cancer cells (NCI-H460). The antitumor activity is significantly reduced when the steric hindrance is increased at the C5′-stereocenter.
