61824-46-2

Usage

InChI:InChI=1/C11H14O2/c1-3-4-10-5-7-11(8-6-10)13-9(2)12/h5-8H,3-4H2,1-2H3

Upstream product

• 645-56-7 4-n-Propylphenol 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 103-65-1 phenylpropane 

Downstream Products

• 1990-24-5 2-hydroxy-5-n-propyl-acetophenone 
• 742078-65-5 2-acetyl-4-propylphenyl benzoate 
• 742078-76-8 1-(2-hydroxy-5-propylphenyl)-3-phenylpropane-1,3-dione 
• 3354-53-8 2-ethyl-4-propylphenol 
• 855839-47-3 acetic acid-(2-ethyl-4-propyl-phenyl ester) 
• 1391854-10-6 (R)-1-phenyl-2,2,2-trichloroethyl (R)-1-(4-acetoxyphenyl)propylcarbamate 
• 1391854-11-7 C₂₀H₂₀Cl₃NO₄ 
• 714-23-8 4-(2-oxopropyl)phenyl acetate 
• 25743-56-0 4-(1-oxopropyl)phenyl acetate 
• 129319-15-9 (+/-)-2',3'-dihydroacetoxychavicol acetate 

Relevant academic research and scientific papers

Palladium-catalyzed acetoxylation of arenes by novel sulfinyl n-heterocyclic carbene ligand complexes

A series of novel ligands based on N-heterocyclic carbene and sulfoxide functionalities have been prepared and characterized. Pd(II) complexes have been synthesized by transmetalation from the corresponding NHC-Ag derivatives, and their behavior as catalysts has been studied in arene C-H bond oxidative activation. Studies conducted toward the elucidation of the reaction mechanism of the acetoxylation suggest a C-H activation step at Pd(IV) rather than Pd(II) intermediates.

O-acylation of substituted phenols with various alkanoyl chlorides under phase-transfer catalyst conditions

Esterification of several types of mono-and disubstituted phenols with various mono-and dialkanoyl chlorides was performed in phase-transfer catalysis conditions, using tetrabutylammonium chloride in a mixture of aqueous NaOH and dichloromethane. The process is particularly efficient (almost quantitative yields) as well as rapid (only 5 min reaction time, at a temperature of0°C). Taylor & Francis Group, LLC.

Synthesis and evaluation of [2-(4-quinolyloxy)phenyl]methanone derivatives: Novel selective inhibitors of transforming growth factor-β kinase

We synthesized and evaluated various [2-(4-quinolyloxy)phenyl]methanone derivatives. These compounds had novel chemical structures that were distinct from those of previously reported inhibitors. Biological data suggested that these compounds inhibited transforming growth factor-β signaling by interacting with the ATP-binding pocket of the transforming growth factor-β type I receptor kinase domain. Here, we report on the synthesis and structure-activity relationships of the compounds in this series.

O-acylation mechanism of p-substituted phenols with various alkanoyl chlorides under phase transfer catalysis conditions

The phenolic ester synthesis between equimolecular amounts of phenols and various alkanoyl chlorides in the presence of aqueous sodium hydroxide solution in a two-phase system (20 mL of each 10% NaOH and dicloromethane, respectively) was reinvestigated under PTC conditions (10 mmol of tetrabutyl ammonium chloride, BNC). The esterification was complete within several minutes and the obtained ester was in high purity. For example, phenyl acetate was obtained quantitatively at 0°C in 5 minutes using a stoichiometric amount of BNC. This acylation procedure is technically simple and does not require anhydrous conditions. A bimolecular electrophilic attack of alkanoyl chloride against the ion-pair in the organic phase, which was formed between the quaternary ammonium cation and the phenoxide anion, must be a rate-determining step, because a plot of the logarithm of relative rate constants of various alkanoyl chlorides vs Taft's polar substituents constants (taking into account the steric constants, Es) gave a good linear relationship. We have found a simple, rapid, convenient, easily separating and efficient PTC technique to synthesize phenolic esters.

Refinement and evaluation of a pharmacophore model for flavone derivatives binding to the benzodiazepine site of the GABAA receptor

To further develop and evaluate a pharmacophore model previously proposed by Cook and co-workers (Drug Des. Discovery 1995, 12, 193-248) for ligands binding to the benzodiazepine site of the GABAA receptor, 40 new flavone derivatives have been synthesized and their affinities for the benzodiazepine site have been determined. Two new regions of steric repulsive interactions between ligand and receptor have been characterized, and the receptor region in the vicinity of 6- and 3′-substituents has been mapped out. 2′-Hydroxy substitution is shown to give a significant increase in affinity, which is interpreted in terms of a novel hydrogen bond interaction with the previously proposed hydrogen bond-accepting site A2. On the basis of the results of these studies and the refined pharmacophore model, 5′-bromo-2′-hydroxy-6-methylflavone, the highest affinity flavone derivative reported so far (Ki = 0.9 nM), was successfully designed. A comparison of the pharmacophore model with a recently proposed alternative model (Marder; et al. Bioorg. Med. Chem., 2001, 9, 323-335) has been made.

Process for synthesis of 5-alkylbenzodioxoles

The following description refers to a new process for the synthesis of 5-alkylated benzo[1,3]dioxole, comprising the following steps in sequence: catalytic hydrogenation of 4-acylphenol; acylation; displacement catalysed by Lewis acids; treatment with an inorganic basic compound and hydrogen peroxide; reaction with alkyl dihalides or dialkoxyalkanes. The process described herein, which yields 5-alkylbenzo[1,3]dioxoles, is economic and can be easily scaled up to industrial size.

Process for the synthesis of 5-allybenzodioxoles

The following description refers to a new process for the synthesis of 5-alkylated benzo[1,3]dioxole, consisting in the following steps in sequence: catalytic hydrogenation of 4-acylphenol; acylation; displacement catalysed by Lewis acids; treatment with an inorganic basic compound and hydrogen peroxide; reaction with alkyl dihalides or dialkoxyalkanes. The process described herein, which yields 5-alkylbenzo[1,3]dioxoles, is economic and can be easily scaled up to industrial size.