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4'-Methoxychalcone is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

22966-19-4

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22966-19-4 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

Check Digit Verification of cas no

The CAS Registry Mumber 22966-19-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,9,6 and 6 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 22966-19:
(7*2)+(6*2)+(5*9)+(4*6)+(3*6)+(2*1)+(1*9)=124
124 % 10 = 4
So 22966-19-4 is a valid CAS Registry Number.

22966-19-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(4-methoxyphenyl)-3-phenyl-2-propen-1-one

1.2 Other means of identification

Product number -
Other names 4-methoxychalcone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:22966-19-4 SDS

22966-19-4Relevant articles and documents

Crystal structure of a chalcone derivative

Devarajegowda,Sridhar,Prasad, J. Shashidhara,Indira,Sooryanarayanarao,Karat, Prakash P.

, p. 145 - 152 (2001)

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.

Recyclable Copper Nanoparticles-Catalyzed Hydroboration of Alkenes and β-Borylation of α,β-Unsaturated Carbonyl Compounds with Bis(Pinacolato)Diboron

Shegavi, Mahadev L.,Saini, Suresh,Bhawar, Ramesh,Vishwantha, Meghana Desai,Bose, Shubhankar Kumar

supporting information, p. 2408 - 2416 (2021/03/16)

Nano-ferrite-supported Cu nanoparticles (Fe-dopamine-Cu NPs) catalyzed anti-Markovnikov-selective hydroboration of alkenes with B2pin2 is reported under mild reaction conditions. This protocol can be applied to a broad range of substrates with high functional group compatibility. In addition, we demonstrated the use of Fe-dopamine-Cu NPs as a catalyst for the β-borylation of α,β-unsaturated ketones and ester, providing alkylboronate esters in up to 98% yield. Reuse of the magnetically recyclable catalyst resulted in no significant loss of activity in up to five reaction runs for both systems. (Figure presented.).

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

Hall, Thomas H.,Adams, Hannah,Vyas, Vijyesh K.,Michael Chu,Wills, Martin

, (2020/12/07)

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.

A new method for the synthesis of chalcone derivatives promoted by PPh3/I2under non-alkaline conditions

Xue, Kangsheng,Sun, Guoxiang,Zhang, Yanzhi,Chen, Xubing,Zhou, Yang,Hou, Jinjun,Long, Huali,Zhang, Zijia,Lei, Min,Wu, Wanying

supporting information, p. 625 - 634 (2020/11/23)

A straightforward and general method has been developed for the synthesis of chalcone derivatives by a Claisen-Schmidt reaction in the presence of PPh3/I2 in 1,4-dioxane under reflux temperatures. With the condensation of the aromatic ketone and aldehyde occurring at non-strongly alkaline conditions, our proposed method significantly expands the range of applicable substrates, especially for groups that are unstable under alkaline conditions.

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

Mellado, Marco,González, César,Mella, Jaime,Aguilar, Luis F.,Vi?a, Dolores,Uriarte, Eugenio,Cuellar, Mauricio,Matos, Maria J.

, (2021/02/12)

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.

Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC

Bolm, Carsten,Molitor, Claude,Rissanen, Kari,Schumacher, Christian,Smid, Sabrina,Truong, Khai-Nghi

, p. 14213 - 14222 (2021/09/07)

A mechanochemical van Leusen pyrrole synthesis with a base leads to 3,4-disubstitued pyrroles in moderate to excellent yields. The developed protocol is compatible with a range of electron-withdrawing groups and can also be applied to the synthesis of oxazoles. Attempts to mechanochemically convert the resulting pyrroles into porphyrins proved to be difficult.

Reaction rate differences between organotrifluoroborates and boronic acids in BINOL-catalyzed conjugate addition to enones

Brooks, Bailey,Hiller, Noemi,May, Jeremy A.

supporting information, (2021/09/28)

Enantioselective organocatalysis has been successfully employed in combination with trifluoroborate reagents for novel organic transformations over the last decade. However, no experimental rate studies of these reactions have been reported. Herein we report Hammett plot analysis of the organocatalyzed enantioselective conjugate addition of alkenyl, aryl, and heteroaryl trifluoroborate salts to chalcone derivatives with substitution at both the β-aryl and keto-aryl positions. The rate trend for keto-aryl substitution diverges from that of boronic acid nucleophiles in that the keto-aryl substituent for trifluoroborate salts does not measurably impact reaction rate in a manner consistent with charge stabilization. In addition, variable temperature NMR in combination with quantitative thin-layer chromatography (TLC) analysis suggests that the reaction is impacted by the low solubility of the trifluoroborate salts, so particle size and stirring speed affect reaction rates.

C3 amino-substituted chalcone derivative with selective adenosine rA1 receptor affinity in the micromolar range

Janse van Rensburg, Helena D.,Legoabe, Lesetja J.,Terre’Blanche, Gisella

, p. 1581 - 1605 (2020/11/20)

Abstract: To identify novel adenosine receptor (AR) ligands based on the chalcone scaffold, herein the synthesis, characterization and in vitro and in silico evaluation of 33 chalcones (15–36 and 37–41) and structurally related compounds (42–47) are reported. These compounds were characterized by radioligand binding and GTP shift assays to determine the degree and type of binding affinity, respectively, against rat (r) A1 and A2A ARs. The chalcone derivatives 24, 29, 37 and 38 possessed selective A1 affinity below 10?μM, and thus, are the most active compounds of the present series; compound 38 was the most potent selective A1 AR antagonist (Ki (r) = 1.6?μM). The structure–affinity relationships (SAR) revealed that the NH2-group at position C3 of ring A of the chalcone scaffold played a key role in affinity, and also, the Br-atom at position C3′ on benzylidene ring B. Upon in vitro and in silico evaluation, the novel C3 amino-substituted chalcone derivative 38—that contains an α,?-unsaturated carbonyl system and easily allows structural modification—may possibly be a synthon in future drug discovery. Graphic abstract: C3 amino-substituted chalcone derivative (38) with C3′ Br substitution on benzylidene ring B possesses selective adenosine rA1 receptor affinity in micromolar range.[Figure not available: see fulltext.]

Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process

Du, Chan,Fang, Jianghua,Fang, Yewen,Lei, Wan,Li, Yan,Liu, Yongjun

supporting information, p. 8502 - 8506 (2021/10/20)

Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developedviathe reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated.

Alkene Synthesis by Photo-Wolff-Kischner Reaction of Sulfur Ylides and N-Tosylhydrazones

Gao, Pan-Pan,Yan, Dong-Mei,Bi, Ming-Hang,Jiang, Min,Xiao, Wen-Jing,Chen, Jia-Rong

supporting information, p. 14195 - 14201 (2021/09/20)

A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity. A series of mechanistic studies support that the reaction should proceed through a radical-carbanion crossover pathway, specifically involving addition of photo-generated sulfur ylide radical cations to N-tosylhydrazones to form carbanions and subsequent Wolff-Kischner process.

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