15753-84-1

Basic information

• Product Name: (E)-4-(3-methylphenyl)but-3-en-2-one
• Synonyms: (E)-4-(3-methylphenyl)but-3-en-2-one
• CAS NO: 15753-84-1
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.21
• Mol File: 15753-84-1.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 278.6°Cat760mmHg
• Flash Point: 100.4°C
• Appearance: /
• Density: 0.999g/cm³
• Vapor Pressure: 0.00423mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: (E)-4-(3-methylphenyl)but-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-(3-methylphenyl)but-3-en-2-one(15753-84-1)
• EPA Substance Registry System: (E)-4-(3-methylphenyl)but-3-en-2-one(15753-84-1)

Safety Data

• Hazardous Substances Data: 15753-84-1(Hazardous Substances Data)

Usage

General Description

(E)-4-(3-methylphenyl)but-3-en-2-one is a chemical compound with the molecular formula C11H12O. It is a ketone with a 3-methylphenyl group attached to the fourth carbon of a but-3-en-2-one chain. (E)-4-(3-methylphenyl)but-3-en-2-one is commonly used as a starting material in organic synthesis and as a building block to create more complex molecules. It has a strong aromatic odor and is often used in the perfume and fragrance industry. It may also have potential applications in pharmaceuticals and agrochemicals due to its unique chemical structure. Overall, (E)-4-(3-methylphenyl)but-3-en-2-one is a versatile and important compound in the field of organic chemistry.

InChI:InChI=1/C11H12O/c1-9-4-3-5-11(8-9)7-6-10(2)12/h3-8H,1-2H3/b7-6+

Upstream product

• 102611-24-5 4-(3-methylphenyl)butan-2-one 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 620-23-5 m-tolyl aldehyde 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 100-80-1 3-methylstyrene 
• 1161837-47-3 1-(meta-tolyl)but-2-yn-1-ol 
• 243867-56-3 3-(3'-methylphenyl)cyclobutan-1-one 
• 67-64-1 acetone 
• 625-95-6 3-Iodotoluene 
• 78-94-4 methyl vinyl ketone 

Downstream Products

• 1421697-75-7 (4R,12bS)-4-m-tolyl-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one 
• 1421697-74-6 (4S,12bS)-4-m-tolyl-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one 
• 762243-26-5 5-m-tolyl-cyclohexane-1,3-dione 

Relevant articles and documents

Dual ReVCatalysis in One-Pot Consecutive Meyer–Schuster and Diels–Alder Reactions

A readily available oxo-ReVcatalyst has been shown to promote a one-pot multistep process that involves the Meyer–Schuster rearrangement of alkynols followed by the Diels–Alder cycloaddition of the resulting enones. These reactions were performed under mild conditions in the presence of 5 mol-% of the catalyst to afford the cycloadducts in good yields with almost 100 % endo stereoselectivity. In-depth computational studies of the cycloaddition mechanism provided the preferred geometry of the rhenium complex in the transition state (TS) and corroborated the experimental endo selectivity.

Asymmetric synthesis of multi-substituted spiro[5,5]undecane-1,5,9-triones via organocatalytic three-component reaction

The asymmetric domino three-component Knoevanagel-Diels-Alder addition (ATCDA) reaction, as an important methodology, has been utilized to construct complex product from ordinary starting materials. In this report, many typical organoamine catalysts were investigated to achieve highly efficient asymmetric three-component reaction of enones 2, aldehydes 3 and Meldrum's acid 4. Various pharmacological multi-substituted spiro[5,5]undecane-1,5,9-triones promoted by 9-amino-9-deoxy-epi-quinine 1 g in one-pot, were obtained in moderate to good yields (up to 81%) with excellent diastereo-(>99:1 dr) and enantioselectivities (up to 97% ee). Meanwhile, based on the controlled experiments and analytical data, a reasonable mechanism of dual-activity for this reaction has been proposed.

8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study

β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.

Sequential Two-Step Stereoselective Amination of Allylic Alcohols through the Combination of Laccases and Amine Transaminases

A sequential two-step chemoenzymatic methodology for the stereoselective synthesis of (3E)-4-(het)arylbut-3-en-2-amines in a highly selective manner and under mild reaction conditions is described. The approach consists of oxidation of the corresponding racemic alcohol precursors by the use of a catalytic system made up of the laccase from Trametes versicolor and the oxy-radical TEMPO, followed by the asymmetric reductive bio-transamination of the corresponding ketone intermediates. Optimisation of the oxidation reaction, exhaustive amine transaminase screening for the bio-transaminations and the compatibility of the two enzymatic reactions were studied in depth in search of a design of a compatible sequential cascade. This synthetic strategy was successful and the combinations of enzymes displayed a broad substrate scope, with 16 chiral amines being obtained in moderate to good isolated yields (29–75 %) and with excellent enantiomeric excess values (94 to >99 %). Interestingly, both amine enantiomers can be achieved, depending on the selectivity of the amine transaminase employed in the system.