1117-74-4Relevant academic research and scientific papers
Insights into β-ketoacyl-chain recognition for β-ketoacyl-ACP utilizing AHL synthases
Nhu Lam, Mila,Dudekula, Dastagiri,Durham, Bri,Collingwood, Noah,Brown, Eric C.,Nagarajan, Rajesh
, p. 8838 - 8841 (2018)
Beta-ketoacyl-ACP utilizing enzymes in fatty acid, polyketide and acyl-homoserine lactone biosynthetic pathways are important targets for developing antimicrobial, anticancer and antiparasitic compounds. Published reports on successful isolation of beta-ketoacyl-ACPs in a laboratory remain scarce to date and thus most beta-ketoacyl-ACP utilizing enzymes are routinely characterized using small molecule substrates in lieu of the bonafide 3-oxoacyl-ACPs. We report the systematic investigation into the electronic, geometric and spatial aspects of beta-ketoacyl-chain recognition to develop 3-oxoacyl-ACP substrate mimics for two beta-ketoacyl-ACP utilizing quorum signal synthases.
Production and upgrading of 5-hydroxymethylfurfural using heterogeneous catalysts and biomass-derived solvents
Gallo, Jean Marcel R.,Alonso, David Martin,Mellmer, Max A.,Dumesic, James A.
, p. 85 - 90 (2013)
High yields of HMF from glucose can be achieved using biomass-derived solvents and a combination of solid Lewis and Bronsted catalysts in a salt-free reaction system. The HMF produced in this system can be oxidized to FDCA or hydrogenated to DMF, both being high-value chemicals.
Facile and Inexpensive Synthesis of 4-Oxoalkanoic Acids from Primary Nitroalkanes and Acrolein
Ballini, Roberto,Petrini, Marino
, p. 1024 - 1026 (1986)
4-Oxoalkanoic acids, useful organic compounds, are easily prepared by conjugate addition of primary aliphatic nitro compounds to acrolein on alumina surface, in the absence of a solvent, and subsequent oxidation with hydrogen peroxide/potassium carbonate.
Free-Radical Carbocyanation of Olefins
Hassan, Haitham,Pirenne, Vincent,Wissing, Maren,Khiar, Chahinaz,Hussain, Ashique,Robert, Frédéric,Landais, Yannick
, p. 4651 - 4658 (2017)
The free-radical three-component carbocyanation of electron-rich olefins was investigated with p-tosyl cyanide as cyanide source. The scope and limitations of the process were established by varying the nature of the alkene and radical precursor. Carbocyanation of chiral allylsilanes was shown to occur with high diastereocontrol, leading to syn β-silyl nitriles. The origin of the stereocontrol was rationalized by a Felkin–Anh-type transition-state model. Finally, a tin-free carbocyanation process was also devised, based on the use of a new alkylsulfonyl cyanide incorporating both carbon fragments to be added across the olefinic π system.
An Efficient Approach to β-Oxoadipate Derivatives and γ-Oxo Acids by the Reformatsky Reaction of Ethyl α-Bromoalkanoates with Succinic Anhydride
Schick, Hans,Ludwig, Ralf
, p. 369 - 370 (1992)
Ethyl 2-bromoalkanoates react with zinc and succinic anhydride in dimethylformamide forming 2-substituted 1-ethyl hydrogen 3-oxoadipates (hexanedioates) isolable in a yield of 56 - 78percent.When subjected to decarboxylative saponification, they afford 4-oxoalkanoic acids in overall yields of 50 - 72percent
A FACILE SYNTHESIS OF 4-OXO CARBOXYLIC ACIDS FROM γ-BUTYROLACTONE
Fuentes, Lelia M.,Larson, Gerald L.
, p. 271 - 274 (1982)
An efficient, high-yield, three-step preparation of 4-oxo carboxylic acids from γ-butyrolactone via silylation and reaction with a Grignard reagent is presented.
Asymmetric synthesis of 2-alkyl-substituted 2-hydroxyglutaric acid γ-lactones
Paju, Anne,Laos, Marit,J?gi, Artur,P?ri, Malle,J??laid, Raissa,Pehk, T?nis,Kanger, T?nis,Lopp, Margus
, p. 4491 - 4493 (2006)
3-Alkyl-1,2-cyclopentanediones 1 are transformed into 2-alkyl-2-hydroxyglutaric acid γ-lactones 3 in up to 83% isolated yields and up to 96% ee, affording a simple access to many bioactive compounds, including diacylglycerol lactones (DAG-lactones).
Stereoselective Synthesis of Polysubstituted Tetrahydropyranones via Acid-Promoted Cyclization of β-Silyl-γ-ethylidene-γ-butyrolactones with Aldehydes and Ketones
Ariyoshi, Shoma,Sakaguchi, Kazuhiko,Nishimura, Takahiro
, p. 11884 - 11894 (2021/09/02)
β-Silyl-γ-ethylidene-γ-butyrolactone upon one-pot treatment with aldehydes and ketones in the presence of Lewis acids underwent a tandem Hosomi-Sakurai/Prins cyclization to give polysubstituted tetrahydropyranones stereoselectively. Various aldehydes and ketones can be used in this reaction to produce the corresponding tetrahydropyranones. The optical purity of the starting γ-butyrolactone was substantially retained in the resulting tetrahydropyranones.
Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diolsviapressure hydrogenation of potentially biobased platform molecules using Kn?lker-type catalysts
Alsters, Paul L.,Chou, Khi Chhay,De Wildeman, Stefaan M. A.,Faber, Teresa,Hadavi, Darya,Han, Peiliang,Quaedflieg, Peter J. L. M.,Schwalb Freire, Alfonso J.,Verzijl, Gerard K. M.,van Slagmaat, Christian A. M. R.
supporting information, p. 10102 - 10112 (2021/08/03)
The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Kn?lker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, thecis-transratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.
Palladium(II)-Catalyzed C(sp 3)-H Activation of N,O-Ketals towards a Method for the β-Functionalization of Ketones
Ho, Danny K.H.,Calleja, Jonas,Gaunt, Matthew J.
, p. 454 - 458 (2019/02/26)
A method for the formal β-functionalization of aliphatic ketones via a palladium-catalyzed sp 3 C-H activation pathway is reported. An N,O-ketal directs an aliphatic C-H carbonylation to form γ-lactams which upon hydrolysis generate γ-keto carb
