13618-19-4Relevant academic research and scientific papers
Copper-catalyzed methylation of 1,3-diketones with tert-butyl peroxybenzoate
Zhou, Zhi-Hao,Li, Cheng-Kun,Zhou, Shao-Fang,Shoberu, Adedamola,Zou, Jian-Ping
, p. 2740 - 2746 (2017/04/18)
Copper-catalyzed radical methylation of 1,3-diketones with tert-butyl peroxybenzoate in air is described, providing a general pathway to α-methyl 1,3-diketones in moderate to good yields. This protocol has been scaled up to 50?g, and one of the synthesized products can be used in the synthesis of medicine, Rosuvastatin.
Method for preparing 2-methyl-1,3-dicarbonyl derivative
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Paragraph 0035, (2016/10/08)
The invention discloses a method for preparing a 2-methyl-1,3-dicarbonyl derivative. A 1,3-dicarbonyl derivative serves as an initiator, raw materials are easy to obtain, and a great variety of raw materials are available. The product obtained through the method has high type diversity and can be used directly or used for other further reactions. Besides, only organic peroxides and a catalytic amount of inorganic copper salt are used, so that cost is low. According to the method, a reaction is conducted in air, reaction conditions are mild, pollution is small, reaction time is short, the yield of the target product is high, reaction operation and aftertreatment are easy, and the method is suitable for industrial production.
Synthesis of β-hydroxy and β-amino ketones from allylic alcohols catalyzed by ru(η5-C5Ph5)(CO)2Cl
Bartoszewicz, Agnieszka,Jezowska, Martina M.,Laymand, Kevin,Moebus, Juri,Martin-Matute, Belen
experimental part, p. 1517 - 1530 (2012/06/15)
An efficient method for the synthesis of β-hydroxy and β-amino ketones from allylic alcohols catalyzed by Ru(η5-C 5Ph5)(CO)2Cl is described. The influence of the stereoelectronic properties of the catalyst on the reaction outcome has been studied. Optimization of the reaction conditions supressed the formation of undesired side products such as saturated ketones, benzyl alcohols, and α,β-unsaturated ketones. Several aromatic and aliphatic allylic alcohols have been reacted with a large variety of aldehydes or imines to produce β-hydroxy ketones or β-amino ketones, respectively, in yields up to 99a%. Based on experimental data, a mechanism via ruthenium alkoxides and ruthenium aldoxides is proposed. In addition, a C-bound ruthenium enolate has been characterized. β-Hydroxy and β-amino ketones are synthesized from allylic alcohols and aldehydes or imines, respectively. The coupling reaction is catalyzed by Ru(η5-C5Ph5)(CO) 2Cl. Mechanistic investigations support a mechanism via ruthenium alkoxide intermediates.
Ruthenium hydride catalyzed regioselective addition of aldehydes to enones to give 1,3-diketones
Fukuyama, Takahide,Doi, Takashi,Minamino, Satoshi,Omura, Sohei,Ryu, Ilhyong
, p. 5559 - 5561 (2008/09/17)
(Chemical Equation Presented) It all adds up: Straightforward access to 2-alkyl-substituted 1,3-diketones is provided by a regioselective addition of aldehydes to enones catalyzed by the ruthenium hydride catalyst [RuHCl(CO)(PPh3)3]
Triethylgallium as a nonnucleophilic base to generate enolates from ketones
Nishimura, Yoshio,Miyake, Yutaka,Amemiya, Ryo,Yamaguchi, Masahiko
, p. 5077 - 5080 (2007/10/03)
(Chemical Equation Presented) Triethylgallium deprotonated cyclic and acyclic ketones at 125-175°C without forming carbonyl addition products, and the resulting gallium enolates underwent facile C-benzoylation and an aldol reaction. Unsymmetrical ketones were preferentially enolized at the methylene moiety, which was under kinetic control.
Synthesis of β-dicarbonyl compounds using 1-acylbenzotriazoles as regioselective C-acylating reagents
Katritzky, Alan R.,Pastor, Alfredo
, p. 3679 - 3681 (2007/10/03)
1-Acylbenzotriazoles 1 are efficient C-acylation reagents for the regioselective conversion of ketone enolates 2 into β-diketones 3.
Synthesis and Conformational Analysis of Pyranophanes and Pyrylophanium Compounds with Intraannular Substituents
Allwohn Juergen,Brumm, Martin,Frenking, Gernot,Hornivius, Matthias,Massa, Werner,et al.
, p. 503 - 514 (2007/10/02)
The synthesis of dithiapyranophanone 6 and 11 is accomplished by use of the two-components-dilution -principle.Pyrolysis of their bis(sulfones) 7 and 12 gives the pyranophanones 8,19 and 13.Under preservation of conformation the intraannular car
Clemmensen Reduction. X. The Synthesis and Acidolysis of Some Aryl Alkyl Substituted Cyclopropane-1,2-diols
Davis, Brian R.,Hinds, Mark G.,Ting, Philip P. C.
, p. 865 - 875 (2007/10/02)
The synthesis of a number of 1-alkyl-2-arylcyclopropane-1,2-diols is reported.Reductive treatment of suitably substituted 1,3-diketones gave a cyclopropanediyl diacetate from which the diol was obtained.Reaction of these diols with acid gave α-hydroxy ketones, in which an alkyl group, rather than an aryl group, was adjacent to the carbonyl function.Clemmensen reduction of the 1,3-diketones gave products of rearrangement, generally similar to those obtained by acidolysis of the cyclopropane-1,2-diols.The relationship of these results to thermochemical studies on the stability of carboxonium ions is discussed.
Synthesis of 1,3-Dicarbonyl Compounds by the Oxidation of 3-Hydroxycarbonyl Compounds with Corey-Kim Reagent
Katayama, Sadamu,Fukuda, Kinue,Watanabe, Toshio,Yamauchi, Masashige
, p. 178 - 183 (2007/10/02)
A new method for the preparation of various 1,3-dicarbonyl compounds is described.Oxidation of 3-hydroxycarbonyl compounds without substituent at C-2 position by the Corey-Kim reagent (N-chlorosuccinimide-dimethyl sulfide) afforded the stable dimethylsulfonium methylides, which on reductive desulfurization by zinc-acetic acid furnished the 1,3-dicarbonyl derivatives.On the other hand, the same treatment of 2-mono-, or 2,2-disubstituted 3-hydroxy-carbonyl compounds gave directly the corresponding 1,3-dicarbonyl analogous, respectively.
