81764-99-0

Basic information

• Product Name: Benzonitrile, 4-(2-acetyl-3-oxo-1-butenyl)-
• CAS NO: 81764-99-0
• Molecular Formula: C13H11NO2
• Molecular Weight: 213.236
• Mol File: 81764-99-0.mol

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4-(2-acetyl-3-oxo-1-butenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-(2-acetyl-3-oxo-1-butenyl)-(81764-99-0)
• EPA Substance Registry System: Benzonitrile, 4-(2-acetyl-3-oxo-1-butenyl)-(81764-99-0)

Safety Data

• Hazardous Substances Data: 81764-99-0(Hazardous Substances Data)

Upstream product

• 105-07-7 4-cyanobenzaldehyde 
• 123-54-6 acetylacetone 

Downstream Products

• 959984-32-8 4-(3-acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)benzonitrile 
• 1234621-22-7 (rac)-4-(6-acetyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidin-7-yl)benzonitrile 
• 1234620-14-4 (rac)-4-(6-Acetyl-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydrotetrazolo[1,5-a]pyrimidin-7-yl)benzonitrile 

Relevant articles and documents

L-Arginine as a cost-effective and recyclable catalyst for the synthesis of α,β-unsaturated nitriles and ketones in an ionic liquid

L-Arginine catalysed the Knoevenagel condensations of aromatic, heteroaromatic and α,β-unsaturated aldehydes with malononitrile and acetylacetone to afford α,β-unsaturated nitriles and ketones. The reactions were carried out at room temperature in the ionic liquid, 1-ethyl-3-methylimidazolium ethylsulfate. Moderate to excellent yields (45-100%) were achieved. The L-arginine/ionic liquid combination was successfully recycled for fi ve runs without signifi cant loss of activity.

Knoevenagel condensation of aromatic aldehydes with active methylene compounds catalyzed by lipoprotein lipase

A screening of using different lipases to catalyze the Knoevenagel reaction was realized, and lipase lipoprotein (LPL) from Aspergillus niger showed the best catalytic performance. The reaction conditions including solvent, enzyme loading, and temperature were screened to improve the reaction efficiency. Various kinds of substrates were investigated, and almost all the target products were obtained in good to excellent yields (76-98%) with Z configuration exclusively. This procedure provides a novel, green and efficient method for the Knoevenagel condensation of aromatic aldehydes with active methylene compounds.

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 simple method for the preparation of functionalized trisubstituted alkenes and α,β,γ,δ-unsaturated carbonyl compounds by using natural amino acid l-tryptophan

Primary natural amino acid l-tryptophan was used, for the first time, as a catalyst in Knoevenagel condensations of aliphatic, aromatic, hetero-aromatic and α,β-unsaturated aldehydes with less reactive acetylacetone and ethyl acetoacetate. The reactions were carried out at room temperature and gave good yields. It is a convenient entry for preparation of functionalized trisubstituted alkenes and α,β,γ,δ-unsaturated carbonyl compounds.

5-ARYL-SUBSTITUTED DIHYDROPYRIDOPYRIMIDINES AND DIHYDROPYRIDAZINES AND USE THEREOF AS MINERAL CORTICOID ANTAGONISTS

The present application relates to novel aryl-substituted heterobicyclic compounds, a process for their preparation, their use for the treatment and/or prophylaxis of diseases, and their use for the manufacture of medicaments for the treatment and/or prop

SUBSTITUTED 4-ARYL-1,4-DIHYDRO-1,6-NAPHTHYRIDINES AND USE THEREOF

The present application relates to novel substituted 4-aryl-1,4-dihydro-1,6-naphthyridines, a process for their preparation, their use for the treatment and/or prophylaxis of diseases, and their use for the manufacture of medicaments for the treatment and/or prophylaxis of diseases, especially cardiovascular disorders.

Magnesium perchlorate as efficient Lewis acid for the Knoevenagel condensation between β-diketones and aldehydes

A new protocol for the Knoevenagel condensation between β-diketones and aliphatic and aromatic aldehydes promoted by Mg(ClO4)2 under mild conditions is reported.

Substituent Effects on 13C and 1H Chemical Shifts in 3-Benzylidene-2,4-pentanediones

Substituent effects on the 13C and 1H chemical shifts have been studied for derivatives of 3-benzylidene-2,4-pentanedione.A significant correlation has been found between chemical shifts of the Z carbonyl group and (C-2) and Hammett constants, while no correlation has been found for the E carbonyl group (C-4).Attempts have been made to determine the structural factors which influence these effects.The conformation of 3-benzylidene-2,4-pentanediones has been determined by 13C and 1H NMR spectroscopy.