22966-19-4

Basic information

• Product Name: 4'-Methoxychalcone
• Synonyms: (2E)-1-(4-Methoxyphenyl)-3-phenyl-2-propen-1-one;(E)-1-(4-Methoxyphenyl)-3-phenyl-2-propen-1-one;4-Methoxyphenyl [(E)-styryl] ketone
• CAS NO: 22966-19-4
• Molecular Formula: C₁₆H₁₄O₂
• Molecular Weight: 238.28
• EINECS: 213-495-5
• Mol File: 22966-19-4.mol
• Article Data: 150

Chemical Properties

• Boiling Point: 397.5°Cat760mmHg
• Flash Point: 180.5°C
• Appearance: /
• Density: 1.114g/cm³
• CAS DataBase Reference: 4'-Methoxychalcone(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Methoxychalcone(22966-19-4)
• EPA Substance Registry System: 4'-Methoxychalcone(22966-19-4)

Safety Data

• Hazardous Substances Data: 22966-19-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 349, 1950 DOI: 10.1021/ja01157a093Tetrahedron Letters, 25, p. 3861, 1984 DOI: 10.1016/S0040-4039(01)91188-8

Upstream product

• 140-10-3 (E)-3-phenylacrylic acid 
• 100-66-3 methoxybenzene 
• 201230-82-2 carbon monoxide 
• 66107-29-7 4-methoxyphenyl triflate 
• 66680-87-3 (E)-1-phenyl-(2-tributylstannyl)ethene 
• 696-62-8 para-iodoanisole 
• 536-74-3 phenylacetylene 
• 108-90-7 chlorobenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 733-53-9 p-methoxyphenyl(phenyl)iodonium tetrafluoroborate 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 100-07-2 4-methoxy-benzoyl chloride 
• 83624-78-6 1-Cyano-4-hydroxy-3-(4-methoxy-benzoyl)-4-(4-methoxy-phenyl)-2,6-diphenyl-cyclohexanecarboxylic acid ethyl ester 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 83085-62-5 2,5-Bis-(4-methoxy-phenyl)-3-phenyl-3H-[1,2]thiaphosphole 2-sulfide 
• 74007-53-7 3,3-dimethoxy-1-(4-methoxyphenyl)-2-phenylpropan-1-one 
• 84725-18-8 4-carbomethoxy-1-(p-methoxyphenyl)-5-phenyl-cyclohex-1-en-3-one 
• 134045-60-6 5-(4-Methoxy-phenyl)-7-phenyl-3-phenylazo-pyrazolo[1,5-a]pyrimidin-2-ylamine 
• 2657-24-1 1-(4-methoxyphenyl)-3,3-diphenylpropan-1-one 
• 99334-60-8 1-(4-methoxylphenyl)-3-phenylbutan-1-one 
• 171860-04-1 [3-(4-methoxy-phenyl)-3-oxo-1-phenyl-propyl]-malonic acid diethyl ester 
• 101442-04-0 4-(4-methoxyphenyl)-4-oxo-2-phenylbutanenitrile 
• 24788-17-8 1-(4-methoxy-phenyl)-3-phenylpropan-1-ol 
• 27183-37-5 1,10-Bis-(4-methoxy-phenyl)-3,8-diphenyl-decane-1,10-dione 
• 26957-30-2 1-(4-Methoxy-phenyl)-3-phenyl-hexan-1-one 
• 26957-31-3 1-(4-Methoxy-phenyl)-6-methyl-3-phenyl-heptan-1-one 
• 26957-32-4 1-(4-methoxyphenyl)-3,4-diphenylbutan-1-one 
• 2657-25-2 (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one 

Relevant articles and documents

Crystal structure of a chalcone derivative

The crystal and molecular structure of 1-(4-methoxyphenyl)-3-(phenyl)-2-propen-1-one derivative is determined by X-ray diffraction method. The compound, C16H14O2, crystallises in the orthorhombic space group Pbca with a = 10.921(2) A, b = 30.583(1) A, c = 7.535(3) A, V = 2516.7(9) A3, Z = 4, Dcalc = 1.242 Mg/m3, μ = 0.327 mm-1, F000 = 504, λ(MoKα) = 0.71069 A and the structure was refined to R = 0.044.

Asymmetric transfer hydrogenation of unsaturated ketones; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects

A detailed study has been completed on the asymmetric transfer hydrogenation (ATH) of a series of enones using Ru(II) catalysts. Electron-rich rings adjacent to the C[dbnd]O group reduce the level of C[dbnd]O reduction compared to C[dbnd]C. The ATH reaction can readily discriminate between double and triple bonds adjacent to ketones, reducing the double bond but leaving a triple bond intact in the major product.

Combined 3D-QSAR and docking analysis for the design and synthesis of chalcones as potent and selective monoamine oxidase B inhibitors

Monoamine oxidases (MAOs) are important targets in medicinal chemistry, as their inhibition may change the levels of different neurotransmitters in the brain, and also the production of oxidative stress species. New chemical entities able to interact selectively with one of the MAO isoforms are being extensively studied, and chalcones proved to be promising molecules. In the current work, we focused our attention on the understanding of theoretical models that may predict the MAO-B activity and selectivity of new chalcones. 3D-QSAR models, in particular CoMFA and CoMSIA, and docking simulations analysis have been carried out, and their successful implementation was corroborated by studying twenty-three synthetized chalcones (151–173) based on the generated information. All the synthetized molecules proved to inhibit MAO-B, being ten out of them MAO-B potent and selective inhibitors, with IC50 against this isoform in the nanomolar range, being (E)-3-(4-hydroxyphenyl)-1-(2,2-dimethylchroman-6-yl)prop-2-en-1-one (152) the best MAO-B inhibitor (IC50 of 170 nM). Docking simulations on both MAO-A and MAO-B binding pockets, using compound 152, were carried out. Calculated affinity energy for the MAO-A was +2.3 Kcal/mol, and for the MAO-B was ?10.3 Kcal/mol, justifying the MAO-B high selectivity of these compounds. Both theoretical and experimental structure–activity relationship studies were performed, and substitution patterns were established to increase MAO-B selectivity and inhibitory efficacy. Therefore, we proved that both 3D-QSAR models and molecular docking approaches enhance the probability of finding new potent and selective MAO-B inhibitors, avoiding time-consuming and costly synthesis and biological evaluations.