22731-65-3Relevant academic research and scientific papers
Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents
Feng, Xiaoming,He, Qianwen,Liu, Xiaohua,Zhang, Dong,Zhang, Fengcai
supporting information, p. 6961 - 6966 (2021/09/11)
An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.
Kinetic resolution of aryl alkenylcarbinols catalyzed by Fc-PIP
Hu, Bin,Meng, Meng,Jiang, Shanshan,Deng, Weiping
experimental part, p. 1289 - 1294 (2012/08/28)
An effective kinetic resolution of a variety of aryl alkenylcarbinols catalyzed by nonenzymatic acyl transfer catalyst Fc-PIP was developed, affording corresponding unreacted alcohols in good to excellent ee value up to 99% and with selectivity factors up to 24.
The cation exchange resin-promoted coupling of alkynes with aldehydes: one-pot synthesis of α,β-unsaturated ketones
Yadav,Subba Reddy,Vishnumurthy
, p. 4498 - 4500 (2008/09/21)
Alkynes undergo smooth coupling with aldehydes in the presence of Amberlyst-15 at room temperature to produce the corresponding α,β-unsaturated ketones in high yields with E-geometry. The use of an inexpensive, readily available, and recyclable cation exchange resin makes this method quite simple and convenient.
Identification of alkylarene chloromethylation products using gas-chromatographic retention indices
Zenkevich,Makarov
, p. 611 - 619 (2008/03/18)
Gas-chromatographic retention indices on standard nonpolar polydimethylsiloxane stationary phases allow identification of products formed by known organic reactions even without using mass-spectrometric data. The efficiency of this approach was demonstrated by the example of identification of previously uncharacterized chloromethyl derivatives of alkylarenes, including structural isomers of compounds containing several chloromethyl groups, directly in reaction mixtures. Chromatographic analysis of such reaction mixtures allows identification of positional isomers of the starting alkylarenes even when they are present simultaneously. The retention indices were determined for the first time for more than 50 alkyl-(chloromethyl)arenes, by-products of chloromethylation, and chloromethyl derivatives of the simplest alkyl phenyl ketones. Nauka/Interperiodica 2007.
INSECTICIDAL TETRAHYDROINDENOPYRIDINE DERIVATIVES
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Page/Page column 13; 24, (2008/06/13)
Certain tetrahydroindenylpyridine derivatives provide unexpected insecticidal and acaricidal activity. These compounds are represented by formula (I); wherein R, R1, R2, and R3 are fully described herein. In addition, comp
A direct synthesis of α-(hydroxymethyl) and α-alkyl-vinyl alkyl ketones
Kra?em, Jihène Ben,Ayed, Ta?cir Ben,Amri, Hassen
, p. 7077 - 7079 (2007/10/03)
Reaction of 2,4-diketoesters 3a-c with aqueous formaldehyde using potassium carbonate solution as base affords the corresponding α-methylene-β-hydroxyalkanones 4a-c which provide a route to α,β-unsaturated alkyl ketones 6a-e via coupling of α-acetoxymethy
Preparation of α-methylene ketones by direct methylene transfer
Rodrigues, J. Augusto R.,Siqueira-Filho, Ezequias P.,De Mancilha, Moacir,Moran, Paulo J. S.
, p. 331 - 340 (2007/10/03)
Four methods for the preparation of α-methylene ketones by direct methylene transfer are presented. The procedures were optimized in order to obtain high yields.
Baker's yeast reduction of α-methyleneketones
Siqueira Filho, Ezequias P.,Rodrigues, J.Augusto R.,Moran, Paulo J.S.
, p. 847 - 852 (2007/10/03)
The bioreduction of α-methyleneketones, R1C(=O)C(=CH2)R2 (R1 = Me, Et, Pr, iso-Bu, Ph, CH2CH2Ph; R2 = Cl, Me, Et, n-Pr, iso-Pr, n-Bu, n-C6H13, Ph, CH2Ph), was mediated by baker's yeast (Saccharomyces cerevisiae) to obtain the corresponding α-methylketones. The R1 and R2 groups had a significant influence on the rate and enantioselectivity of the reductions. The rate of C=C bond reduction was higher than that of C=O bond reduction. Only α-methyleneketones having R1 = Me yielded α-methylketones in high enantioselectivity with e.e.s of 88-99%.
Azo and Azoxy Compounds: XII. Use of Nitrogen Oxide in Organic Synthesis
Yandovskii,Tselinskii
, p. 147 - 152 (2007/10/03)
Thermal elimination of the alkoxydiazene oxide group from the derivatives of acyl- and benzoylalkanes (cycloalkanes) afforded the corresponding vinyl ketones. Addition of nitrogen oxide and alkoxides to vinyl ketones followed by removal of the acyl group yielded 1,4-dialkoxy-1,2-diazabut-1-ene 2-oxides.
Superacid-catalyzed electrocyclization of 1-phenyl-2-propen-1-ones to 1- indanones. Kinetic and theoretical studies of electrocyclization of oxonium- carbenium dications
Suzuki, Takayoshi,Ohwada, Tomohiko,Shudo, Koichi
, p. 6774 - 6780 (2007/10/03)
Strongly acidic conditions are required to induce the Nazarov-type cyclization of aryl vinyl ketones, although chemical analogy with the Nazarov reaction would superficially imply a straightforward electrocyclization reaction of the O-protonated monocation. In this paper we describe the superacid-catalyzed prototype cyclization of 1-phenyl-2-propen-1-ones. The acidity dependence of these cyclization reactions as revealed by kinetic measurements strongly suggests the involvement of the O,O-diprotonated dication rather than the O-protonated monocation. That is the cyclization of 1-phenyl-2-propen-1-ones represents an electrocyclization of the oxonium- carbenium dication. We also describe the effect of substituents at the 2- position of 1-phenyl-2-propen-1-ones. Ab initio calculations, based on the density functional theory, support the idea that electrocyclization of the dication is energetically more favarable than that of the monocation.
