4224-87-7

Usage

Safety Profile

A poison by intraperitoneal route. Moderately toxic by ingestion. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating vapors.

InChI:InChI=1/C16H14O/c1-13-7-9-14(10-8-13)11-12-16(17)15-5-3-2-4-6-15/h2-12H,1H3/b12-11+

Upstream product

• 32120-82-4 bis(benzoylmethyl) sulfoxide 
• 104-87-0 4-methyl-benzaldehyde 
• 70-11-1 α-bromoacetophenone 
• 1774-66-9 3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 1669-55-2 1-(4-methylphenyl)-3-phenyl-1-propen-3-ol 
• 134539-86-9 1-methyl-4-(3-phenyl-2-propen-1-yl)benzene 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 201230-82-2 carbon monoxide 
• 17763-67-6 Phenyl triflate 
• 19710-56-6 hydroxycarbene 
• 98-80-6 phenylboronic acid 
• 22252-14-8 (E)-3-(4-methylphenyl)-1-phenyl-2-propen-1-one 
• 589-18-4 4-Methylbenzyl alcohol 
• 98-85-1 1-Phenylethanol 

Downstream Products

• 133414-92-3 8-Phenyl-6-p-tolyl-8,9-dihydro-7H-tetrazolo[1,5-b][1,2,4]triazepine 
• 84202-11-9 2-phenyl-4-(p-tolyl)-5,6,7,8-tetrahydrochromenylium triflate 
• 85157-03-5 ethyl 2-oxo-6-(4-methylphenyl)-4-phenyl-3-cyclohexene-1-carboxylate 
• 78831-43-3 (3S,4R,5R,6R)-2,4-Dibenzoyl-6-phenyl-3,5-di-p-tolyl-cyclohexanone 
• 93129-60-3 3,6-diphenyl-5-(4-methylphenyl)-2-cyclohexene-1-one 
• 76983-09-0 2-Oxo-6-phenyl-4-p-tolyl-1,2,3,4-tetrahydro-pyridine-3-carbonitrile 
• 65429-74-5 3-cyano-4-(4-methyl-phenyl)-6-phenyl-1,2-dihydro-pyridine-2-one 
• 74007-52-6 3,3-Dimethoxy-1-phenyl-2-p-tolyl-propan-1-one 
• 74007-61-7 3-Methoxy-2-phenyl-3-p-tolyl-propionic acid methyl ester 
• 38226-67-4 C₂₃H₂₂O₂S 
• 60246-75-5 2,3-dihydro-2-(4'-methylphenyl)-4-phenyl-1,5-benzothiazepine 
• 77198-51-7 5'-amino-4-methyl-[1,1':3',1''-terphenyl]-4',6'-dicarbonitrile 

Relevant academic research and scientific papers

Micellar Catalysis Strategy of Cross-Condensation Reaction: The Effect of Polar Heads on the Catalytic Properties of Aminoalcohol-Based Surfactants

Abstract: The effect of the polar head and the concentration of quaternary ammonium surfactants (C14EtOH, C14iPrOH, C14PrOH, where, 14 = carbon number iPrOH = iso-propanol, EtOH = ethanol, PrOH = propanol) in micellar cata

Electronically tuneable orthometalated RuII–NHC complexes as efficient catalysts for C–C and C–N bond formations via borrowing hydrogen strategy

The catalytic activities of a series of simple and electronically tuneable cyclometalated RuII–NHC complexes (2a–d) were explored in various C–C/N bond formations following the borrowing hydrogen process. Slight modifications in the ligand backbone were noted to tune the activities of these complexes. Among them, the complex 2d featuring a 1,2,4-triazolylidene donor with a 4-NO2–phenyl substituent displayed the highest activity for the coupling of diverse secondary and primary alcohols with a low catalyst loading of 0.01 mol% and a sub-stoichiometric amount of inexpensive KOH base. The efficacy of this simple system was further showcased in the challenging one-pot unsymmetrical double alkylation of secondary alcohols using different primary alcohols. Moreover, the complex 2d also effectively catalyses the selective mono-N-methylation of various aromatic and aliphatic primary amines using methanol to deliver a range of N-methyl amines. Mechanistically, the β-alkylation reaction follows a borrowing hydrogen pathway which was established by the deuterium labelling experiment in combination with various control experiments. Intriguingly, in situ1H NMR and ESI-MS analyses evidently suggested the involvement of a Ru–H species in the catalytic cycle and further, the kinetic studies revealed a first order dependence of the reaction rate on the catalyst as well as the alcohol concentrations.

Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite

Earth abundant metals are much less expensive, promising, valuable metals and could be served as catalysts for the borrowing hydrogen reaction, dehydrogenation and heterocycles synthesis, instead of noble metals. The uniformly dispersed zinc composites were designed, synthesized and carefully characterized by means of XPS, EDS, TEM and XRD. The resulting zinc composite showed good catalytic activity for the N-alkylation of amines with amines, ketones with alcohols in water under base-free conditions, while unsaturated carbonyl compounds could also be synthesized by tuning the reaction conditions. Importantly, it was the first time to realize the synthesis of 2-aryl-1H-benzo[d]imidazole derivatives by using this zinc composite under green conditions. Meanwhile, this zinc catalyst could be easily recovered and reused for at least five times.

Mizoroki–Heck coupling reaction on the surface of sepiolite clay-supported Pd/Cu nanoalloy

Well distributed Pd/Cu bimetallic nanoalloy supported on acid-modified sepiolite (ASEP) was prepared via a solvothermal process. The resulting system, Pd/Cu@ASEP, was characterized using spectroscopic data such as FT-IR, XRD, TEM and ICP-AES. The morphology characterization revealed that the crystalline bimetallic particles were dispersed on ASEP as nanoalloys with diameters ranged from 25 to 30 nm. This system was successfully used for ligand-free Mizoroki-Heck coupling in the presence of air, under mild conditions. This method has advantages compared to other systems, such as short reaction times, high yields, facile catalyst and easy separation and reusability of the catalyst. The catalyst was compatible with a variety of aryl and heteraryl iodides, which provides favorable products with good to high yields. Aryl and heteraryl bromides could also be activated for the Mizoroki-Heck reaction using Pd/Cu@ASEP catalyst, with good to moderate yields.

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

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.).

Synthesis, characterization and biological evaluation of new 3,5-disubstituted-pyrazoline derivatives as potential anti-Mycobacterium tuberculosis H37Ra compounds

A total of fourteen pyrazoline derivatives were synthesized through cyclo-condensation reactions by chalcone derivatives with different types of semicarbazide. These compounds were characterized by IR, 1D-NMR (1H, 13C and Distortionless Enhancement by Polarization Transfer-DEPT-135) and 2D-NMR (COSY, HSQC and HMBC) as well as mass spectroscopy analysis (HRMS). The synthesized compounds were tested for their antituberculosis activity against Mycobacterium tuberculosis H37Ra in vitro. Based on this activity, compound 4a showed the most potent inhibitory activity, with a minimum inhibitory concentration (MIC) value of 17 μM. In addition, six other synthesized compounds, 5a and 5c–5g, exhibited moderate activity, with MIC ranges between 60 μM to 140 μM. Compound 4a showed good bactericidal activity with a minimum bactericidal concentration (MBC) value of 34 μM against Mycobacterium tuberculosis H37Ra. Molecular docking studies for compound 4a on alpha-sterol demethylase was done to understand and explore ligand– receptor interactions, and to hypothesize potential refinements for the compound.

The mechanism of the reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford hydrazones and 2-pyrazolines (4,5-dihydro-1H-pyrazoles): Experimental and theoretical results

The reaction of hydrazines with α,β-unsaturated carbonyl compounds to afford 2-pyrazolines was studied using a dissymmetric chalcone (phenyl/p-tolyl) and three hydrazines, hydrazine itself, phenylhydrazine and thiosemicarbazide. Several products were iden

Enantioselective Stetter Reactions Catalyzed by Bis(amino)cyclopropenylidenes: Important Role for Water as an Additive

The first highly enantioselective intermolecular Stetter reaction using simple enones is reported. A series of novel chiral BAC structures were designed and prepared. They were tested in the Stetter reaction with simple aldehydes and enones. The products were generated in excellent yields and enantioselectivities (up to 94% ee). Surprisingly, a substoichiometric amount of water was crucial to obtain high enantioselectivities. Chiral BACs were also shown to catalyze 1,6-conjugate addition reactions with paraquinone methides enantioselectively.

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.

Inhibition of Caco-2 and MCF-7 cancer cells using chalcones: synthesis, biological evaluation and computational study

Cancer is the second death cause worldwide, with breast and colon cancer among the most prevalent types. Traditional treatment strategies have several side effects that inspire the development of novel anticancer agents derived from natural sources, like chalcone derivatives. For this investigation, twenty-three chalcones (4a-w) were synthesized and evaluated as antiproliferative agents against MCF-7 and Caco-2 cells, finding three and two compounds with similar or higher antiproliferative activity than daunorubicin, while only two chalcones showed better selectivity indexes than daunorubicin on MCF-7. From these results, we developed good-performance QSAR models (r > 0.850, q2>0.650), finding several structural features that could modify chalcone activity and selectivity. According to these models, chalcones 4w and 4t have high potency and selectivity against Caco-2 and MCF-7, respectively, which make them attractive candidates for hit-to-lead development of ROS-independent pro apoptotic agents.