22966-01-4

Basic information

• Product Name: 2-Propen-1-one, 3-(2-methylphenyl)-1-phenyl-, (2E)-
• Synonyms: 2-Methyl-trans-chalkon;2-methyl-trans-chalcone
• CAS NO: 22966-01-4
• Molecular Formula: C16H14O
• Molecular Weight: 222.287
• Mol File: 22966-01-4.mol

Chemical Properties

• Boiling Point: 152 °C(Press: 0.5 Torr)
• Density: 1.078±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-Propen-1-one, 3-(2-methylphenyl)-1-phenyl-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propen-1-one, 3-(2-methylphenyl)-1-phenyl-, (2E)-(22966-01-4)
• EPA Substance Registry System: 2-Propen-1-one, 3-(2-methylphenyl)-1-phenyl-, (2E)-(22966-01-4)

Safety Data

• Hazardous Substances Data: 22966-01-4(Hazardous Substances Data)

Upstream product

• 615-37-2 ortho-methylphenyl iodide 
• 936-59-4 3-chloropropiophenone 
• 89-95-2 2-methyl-benzyl alcohol 
• 98-86-2 acetophenone 
• 201230-82-2 carbon monoxide 
• 98-80-6 phenylboronic acid 
• 98-85-1 1-Phenylethanol 
• 939-57-1 (E)-3-(2-methylphenyl)acrylic acid 
• 611-73-4 Benzoylformic acid 
• 100-52-7 benzaldehyde 
• 577-16-2 2-Methylacetophenone 
• 536-74-3 phenylacetylene 
• 529-20-4 2-methylphenyl aldehyde 

Downstream Products

• 1352733-12-0 (E)-5-styryl-1-(o-tolyl)-1Htetrazole 
• 1352733-28-8 (E)-5-(2-methylstyryl)-1-phenyl-1H-tetrazole 
• 1415453-85-8 C₁₆H₁₆O 
• 84839-91-8 1-phenyl-3-(2-methylphenyl)-1-propananone 

Relevant articles and documents

Catalyst-free synthesis of fused 1,2,3-triazole and isoindoline derivatives: Via an intramolecular azide-alkene cascade reaction

Benzyl bromides bearing an ortho-substituted α,β-unsaturated ketone moiety are found to be promising precursors for the synthesis of fused 1,2,3-triazole and isoindoline derivatives via an intramolecular azide-alkene cascade reaction under catalyst free conditions. Fused 1,2,3-triazole derivatives 2 were synthesized in excellent yields by treating compounds 1 with sodium azide in DMF at room temperature, whereas isoindoline derivatives 3 were produced in moderate to good yields only by slight modification of the reaction conditions. Both reactions call for simple and mild conditions, display broad substrate scopes and result in good regiospecificity.

Ligand-Free Palladium-Catalyzed Carbonylative Suzuki Couplings of Vinyl Iodides with Arylboronic Acids under Substoichiometric Base Conditions

A ligand-free palladium-catalyzed carbonylation of vinyl iodides with arylboronic acids, permitting the synthesis of chalcones and α-branched enones, has been established. This reaction proceeds smoothly at ambient pressure and temperature, and works well even with a substoichiometric amount of base. Importantly, this mild, efficient, and operationally simple protocol is suitable for the late-stage functionalization of an epiandrosterone-derived complex molecule.

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.

Heteroleptic copper(I) complexes as energy transfer photocatalysts for the intermolecular [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides

The [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides can be effectively catalyzed by heteroleptic copper(I) complexes. The reactions were carried out under mild reaction conditions and the products were obtained in 20–72% yield under visible light irradiation. The copper-based photocatalyst comprised of the rigid phenanthroline ligand with substituents at the 2,9-positions and the 4,7-positions showed high activity in the photodimerization via an energy transfer pathway.

Iodine-catalyzed α,β-dehydrogenation of ketones and aldehydes generating conjugated enones and enals

A transition metal-free α,β-dehydrogenation of ketones and aldehydes was developed. This reaction was conducted in a facile I2/KI/DMSO system to produce the corresponding unsaturated compounds in good to high yields. The gram-scale experiment also indicated the potential synthetic value of this new reaction in organic synthesis. In the reaction, DMSO acted as both solvent and mild oxidant.

Donor-acceptor fluorophores as efficient energy transfer photocatalysts for [2 + 2] photodimerization

Mild [2 + 2] photodimerization of enone substrates was induced by donor-acceptor fluorophores. Enone substrates were activated efficiently for anti-head to head dimerizations with a high yield (up to 83%) and high selectivity. The adjustable excited state potential also allows donor-acceptor fluorophores to be used for isomerization of the above substrates, confirming the potential of donor-acceptor fluorophores as energy transfer photocatalysts.

Synthesis of Tetrahydroisoquinolines by Visible-Light-Mediated 6- exo -trig Cyclization of α-Aminoalkyl Radicals

Starting from the respective tertiary α-silylmethyl amines, the intramolecular cyclization of α-aminoalkyl radicals to Michael acceptors produced tetrahydroisoquinolines. The reaction conditions included the use of 5 molpercent of an iridium photoredox catalyst, dimethylformamide as the solvent, and equimolar amounts of water and cesium carbonate as the additives. 13 substrates were synthesized from ortho -alkylbenzaldehydes in a three-step procedure involving a carbonyl condensation, a radical bromination, and a substitution by a secondary α-silylmethyl amine. After optimization of the photocyclization, the reaction delivered tetrahydroisoquinolines in moderate to high yields (41-83percent). A facial diastereoselectivity (dr ? 80:20) was observed with chiral substrates and a crystal structure provided evidence for the relative configuration of the major diastereoisomer. A catalytic cycle with direct electron transfer to the photoexcited metal catalyst is proposed.

Synthesis of α, β - unsaturated ketone method

A synthetic method for [alpha],[beta]-unsaturated ketone is a method which catalyzes a primary alconol and a secondary alcohol to oxidize and couple by a supported catalyst. The method includes the steps of adding the primary alconol, the secondary alcohol, an alkali and the catalyst into the mixed solvent mixing water and tert-butyl alcohol; stirring at 0-100 DEG C for 0.5-36 hours under the existence of an oxidizing agent. The yield of [alpha],[beta]-unsaturated ketone can reach 99% in the oxidation coupling reaction system. The synthetic method is environment friendly and has high atom economy and reaction efficiency. Moreover, the synthetic method uses non-noble metal catalyst, so that the production cost is greatly reduced.

Synthesis of chalcones with antiproliferative activity on the SH-SY5Y neuroblastoma cell line: Quantitative Structure–Activity Relationship Models

Chalcones are a group of molecules with a broad spectrum of biological activities, being especially appealing for their antiproliferative effects on several cancer cell lines. For this reason, we synthesized 23 chalcones with good to excellent yields and assessed their effect on the viability of the SH-SY5Y neuroblastoma cell line and on primary human fibroblasts. The results indicated that 18 of these compounds were more active than 5-fluorouracil in the cancer cell line and one of them was more selective than this reference drug. To identify structural features related to the antiproliferative activity of these compounds, as well as, the selectivity on the cancer cell line, a 2D-QSAR analysis was performed. The QSAR model (q2 = 0.803; r2 = 0.836) showed that lipophilicity (CLogP) is the most important factor to increase their cytotoxicity on the cancer cell line. On the other hand, the selectivity QSAR model (q2 = 0.917; r2 = 0.916) showed that changes in the Mulliken’s charge of the carbonyl group and at the C4’ position in the chalcone core can increase the selectivity for SH-SY5Y cell line compared to normal fibroblasts.

α-Unsubstituted Pyrroles by NHC-Catalyzed Three-Component Coupling: Direct Synthesis of a Versatile Atorvastatin Derivative

A practical one-pot cascade reaction protocol provides direct access to valuable 1,2,4-trisubstituted pyrroles. The process involves an N-heterocyclic carbene (NHC)-catalyzed Stetter-type hydroformylation using glycolaldehyde dimer as a novel C1 building-block, followed by a Paal-Knorr condensation with primary amines. The reaction makes use of simple and commercially available starting-materials and catalyst, an important feature regarding applicability and utility. Low catalyst loading under mild reaction conditions afforded a variety of 1,2,4-substituted pyrroles in a transition-metal-free reaction with high step economy and good yields. This methodology is applied in the synthesis of a versatile Atorvastatin precursor, in which a variety of modifications at the pyrrole core structure are possible.