15725-17-4

Usage

InChI:InChI=1/C13H14O3/c1-9(14)13(10(2)15)8-11-4-6-12(16-3)7-5-11/h4-8H,1-3H3

Upstream product

• 15435-71-9 sodium acetylacetonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 123-54-6 acetylacetone 
• 19350-72-2 N'-(4-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 41002-50-0 4-acetoxy-3-penten-2-one 

Downstream Products

• 85046-00-0 Cyanessigsaeure-(4-methoxybenzyliden)-hydrazid 
• 127381-98-0 4,7-dihydro-4-(4-methoxybenzylidene)-3,5-dimethyl-7-oxo-1H-1,2-diazepine-6-carbonitrile 
• 87497-29-8 1,7-Bis-dimethylamino-4-(4-methoxy-benzylidene)-heptane-3,5-dione; hydrochloride 
• 120811-06-5 5-Amino-3-acetyl-4,7-di(p-methoxyphenyl)-2-methyl-6,7-dihydro-4H-pyrano<2,3-b>pyridine-6,6-dicarbonitrile 
• 105263-07-8 5-acetyl-2-amino-6-methyl-4-(4-methoxy-phenyl)-4H-pyran-3-carbonitrile 
• 123207-06-7 4,4-Dimethoxy-3-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-pentan-2-one 
• 582333-63-9 (Z)-4-(4-Methoxy-phenyl)-3-[1,8]naphthyridin-2-yl-but-3-en-2-one 
• 908589-57-1 (2S,3R)-2-Hydroxy-3-(4-methoxy-phenyl)-2-phenyl-3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-propionic acid 
• 908589-49-1 2-tert-butyl-5-[(4-methoxy-phenyl)-(1,3,5-trimethyl-1H-pyrazol-4-yl)-methyl]-5-phenyl-[1,3]dioxolan-4-one 
• 908589-56-0 (2S,3R)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-2-hydroxy-3-(4-methoxy-phenyl)-2-phenyl-propionic acid 
• 908589-48-0 2-tert-butyl-5-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-(4-methoxy-phenyl)-methyl]-5-phenyl-[1,3]dioxolan-4-one 

Relevant academic research and scientific papers

Antimicrobial, antioxidant and SOD activities of copper(II) complexes derived from 2-aminobenzothiazole derivatives

A series of Cu(II) complexes have been synthesized from bidentate Schiff base ligands (by condensation of Knoevenagel condensate of acetoacetanilide (obtained from substituted benzaldehydes and acetoacetanilide) and 2-aminobenzothiazole). They were charac

Cross-linked polystyrene-TiCl4 complex as a reusable Lewis acid catalyst for solvent-free Knoevenagel condensations of 1,3-dicarbonyl compounds with aldehydes

Cross-linked polystyrene copolymer beads with the average particle size in the range of (50–80 mesh size) were prepared by a new method, characterized and functionalized with titanium tetrachloride to afford the corresponding polystyrene?titanium tetrachloride complex in one step reaction and characterized by FT-IR, UV, TGA, DSC, XRD, SEM, BET. This polymer metal complex (PS/TiCl4) was used as a heterogeneous, recoverable, reusable Lewis acid for solvent-free Knoevenagel condensations of 1,3-diketones with aromatic aldehydes under green and mild conditions. The rate of reactions was found to decrease with an increasing percentage of crosslinking and the mesh size of the copolymer beads. This complex showed good stability and catalytic activity in the Knoevenagel reactions.

Enzyme Promiscuity as a Remedy for the Common Problems with Knoevenagel Condensation

A new protocol based on lipase-catalyzed tandem reaction toward α,β-enones/enoesters is presented. For the synthesis of the desired products the tandem process based on enzyme-catalyzed hydrolysis and Knoevenagel reaction starting from enol acetates and aldehyde is developed. The relevant impact of the reaction conditions including organic solvent, enzyme type, and temperature on the course of the reaction was revealed. It was shown that controllable release of the active methylene compound from the corresponding enol carboxylate ensured by enzymatic reaction diminishes significantly the formation of the unwanted co-products. Furthermore, this protocol was extended by including a second tandem chemoenzymatic transformation engaging various aldehyde precursors. After a careful optimization of the reaction conditions, the target products were obtained with yields up to 86 % and with excellent E/Z-selectivity.

Corrigendum to: Enzyme Promiscuity as a Remedy for the Common Problems with Knoevenagel Condensation (Chemistry – A European Journal, (2019), 25, 43, (10156-10164), 10.1002/chem.201901491)

In the published paper, there is a mistake in the labelling of compounds in Figure. A corrected version of that Figure appears below. The authors apologise for the mistake. Figure (Figure presented.) Unsaturated 2,4-pentanediones obtained by enzyme-catalyzed tandem Knoevenagel reaction. Reaction conditions: aldehyde (1 mmol), 4-acetoxy-3-penten-2-one (5 a, R1=R2=R3=Me) (3 mmol), and PPL (100 mg) in tert-butyl alcohol/ 5 % H2O v/v (2 mL) for 72 h at 20 °C, 200 rpm. [a] With vinyl acetate. [b] With ethyl β-styrylcarbonate. [c] With styryl acetate.

Base-Promoted Tandem Cyclization for the Synthesis of Benzonitriles by C?C Bond Construction

A facile synthesis of benzonitriles via a base-promoted tandem cyclization reaction of α,β-unsaturated enones having electron-withdrawing group (EWG) and 2-acyl-acrylonitriles was developed. This new synthetic method to access benzonitriles is suitable for a wide range of substrates. A plausible reaction mechanism is proposed on the basis of previous literature and our own investigations. (Figure presented.).

A facile synthesis of trisubstituted alkenes from β-diketones and aldehydes with AlCl3 as catalyst

Preparation of trisubstituted alkenes from low-activity β-diketones and aldehydes with aluminum chloride as catalyst has been studied. The frequently used catalyst AlCl3 is used for the first time to promote this condensation. The procedure is a convenient, low toxicity, and highly efficient method for industrial synthesis of trisubstituted alkenes in high yield. Springer Science+Business Media B.V. 2011.

Enzyme catalytic promiscuity: The papain-catalyzed Knoevenagel reaction

Papain as a sustainable and inexpensive biocatalyst was used for the first time to catalyze the Knoevenagel reactions in DMSO/water. A wide range of aromatic, hetero-aromatic and α,β-unsaturated aldehydes could react with less active methylene compounds acetylacetone and ethyl acetoacetate. The products were obtained in moderate to excellent yields with Z/E selectivities of up to 100:0. This case of biocatalytic promiscuity not only widens the application of papain to new chemical transformations, but also could be developed into a potentially valuable method for organic synthesis.

COMPOSITIONS AND METHODS FOR STABILIZING INGREDIENTS USING 2,4-PENTANEDIONE COMPOUNDS

Benzylidene substituted 2,4-pentanedione compounds without having phenolic hydroxyl group(s) are found to provide photostability to otherwise photosensitive compounds and compositions.

Efficient solvent-free knoevenagel condensation between -diketone and aldehyde catalyzed by silica sulfuric acid

Silica sulfuric acid has been utilized as an efficient heterogeneous recyclable catalyst for Knoevenagel condensation between poorly reactive β-diketones and aldehydes under solvent-free conditions. This protocol also works well with more reactive β-ketoesters. The condensation is efficient, clean, and mild. The scope and generality of the Knoevenagel condensation were investigated. The procedure led only to the Knoevenagel product, and no side product derived from a subsequent Michael βaddition of -diketone to alkene was detected at rt. Increasing temperature led to a subsequent Michael addition, and it was applied to the efficient synthesis of 9-aryl-1,8-dioxo- octahydroxanthene derivatives.

A systematic study on Knoevenagel reaction and Nazarov cyclization of less reactive carbonyl compounds using rare earth triflates and its applications

A systematic study of Knoevenagel reaction and Nazarov cyclization was made on variety of less reactive carbonyl compounds such as β-ketoesters, 1,3-diketones and cyclic active methylene compounds using Yb(OTf)3 as the catalyst. Recycling study confirms reusability of the catalyst without much loss of activity.