1901-26-4

Usage

Chemical Properties

3-Methyl-4-phenyl-3-butene-2-one has a fruity, berry, camphor-like odor.

Preparation

By condensation of benzaldehyde with butanone in the presence of dry, gaseous HCl at low temperature

InChI:InChI=1/C11H12O/c1-9(10(2)12)8-11-6-4-3-5-7-11/h3-8H,1-2H3/b9-8+

Upstream product

• 100-52-7 benzaldehyde 
• 78-93-3 butanone 
• 873-49-4 cyclopropylbenzene 
• 108-24-7 acetic anhydride 
• 7647-01-0 hydrogenchloride 
• 104174-46-1 C₁₁H₁₄O 
• 78808-42-1 2-methyl-1-phenylbuta-2,3-dien-1-ol 
• 100-51-6 benzyl alcohol 

Downstream Products

• 109392-97-4 (Z)-5-Dimethylamino-2-methyl-1-phenyl-pent-1-en-3-one 
• 71023-56-8 2,3-Dimethyl-1-phenyl-fluoranthene 
• 52466-45-2 ethyl 4-ethoxy-5-methyl-2-oxo-6-phenyl-3-cyclohexenecarboxylate 
• 10509-34-9 (E)-2,3-Dimethyl-1-phenyl-pent-1-en-4-yn-3-ol 
• 13705-37-8 3,3-dimethyl-4-phenyl-2-butanone 
• 21869-55-6 3-methyl-4-phenylbutan-2-one 
• 76539-89-4 5-Methyl-6-phenyl-4-pyrrolidin-1-yl-5,6-dihydro-thiopyran-2-thione 
• 76539-88-3 5-Methyl-6-phenyl-4-piperidin-1-yl-5,6-dihydro-thiopyran-2-thione 
• 76539-87-2 5-Methyl-4-morpholin-4-yl-6-phenyl-5,6-dihydro-thiopyran-2-thione 
• 76539-86-1 4-Diethylamino-5-methyl-6-phenyl-5,6-dihydro-thiopyran-2-thione 
• 15934-57-3 3-phenyl-4-methylpentan-2-one 
• 76539-85-0 4-Dimethylamino-5-methyl-6-phenyl-5,6-dihydro-thiopyran-2-thione 
• 16736-20-2 (Z)-2-Methyl-5-morpholin-4-yl-1-phenyl-pent-1-en-3-one; hydrochloride 
• 119449-45-5 2-Methyl-4-methylene-2-((Z)-1-methyl-2-phenyl-vinyl)-tetrahydro-furan 

Relevant academic research and scientific papers

Intraparticle Diffusional versus Site Effects on Reaction Pathways in Liquid-Phase Cross Aldol Reactions

Chemo- and regioselectivity in a heterogeneously catalyzed cross aldol reaction were directed by tuning the nature of the sites, textural properties, and reaction conditions. Catalysts included sulfonic acid-functionalized resins or SBA-15 with varying particle size or pore diameter, H-BEA zeolites, and Sn-BEA zeotype; conditions were 25 °C to 170 °C in organic media. Benzaldehyde and 2-butanone yielded branched (reaction at -CH2- of butanone) and linear (reaction at -CH3) addition and condensation products; and fission of the branched aldol led to β-methyl styrene and acetic acid. Strong acids promoted the dehydration step, and regioselectivity originated from preferred formation of the branched aldol. Both, resins and functionalized SBA-15 materials yielded predominantly the branched condensation product, unless particle morphology or temperature moved the reaction into the diffusion-limited regime, in which case more fission products were formed, corresponding to Wheeler Type II selectivity. For H-form zeolites, fission of the branched aldol competed with dehydration of the linear aldol, possibly because weaker acidity or steric restrictions prevented dehydration of the branched aldol.

Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters

Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.

Organoseleno-catalyzed synthesis of α,β-unsaturated α′-Alkoxy ketones from allenes enabled by se···o interactions

α,β-Unsaturated α′-Alkoxy ketones have been prepared under mild conditions from allenes using water as the oxygen source and without the necessity of metals. The organocatalytic oxygenation-rearrangement sequence displays an exquisite chemo-, stereo-, and

RhIII-Catalyzed Synthesis of Highly Substituted 2-Pyridones using Fluorinated Diazomalonate

A RhIII-catalyzed strategy was developed for the rapid construction of highly substituted 2-pyridone scaffolds using α,β-unsaturated oximes and fluorinated diazomalonate. The reaction proceeds through direct, site-selective alkylation based on migratory insertion and subsequent cyclocondensation. A wide substrate scope with different functional groups was explored. The requirement of fluorinated diazomalonate was explored for this transformation. The developed methodology was further extended with the synthesis of the bioactive compound.

Mild Chemoenzymatic Oxidation of Allylic sec-Alcohols. Application to Biocatalytic Stereoselective Redox Isomerizations

The design of catalytic oxidative methodologies in aqueous medium under mild reaction conditions and using molecular oxygen as final electron acceptor represents a suitable alternative to the traditional oxidative transformations. These methods are especially relevant if other functionalities that can be oxidized are present within the same molecule, as in the case of allylic alcohols. Herein we apply a simple chemoenzymatic system composed of the laccase from Trametes versicolor and 2,2,6,6-tetramethylpiperidinyloxy radical (TEMPO) to oxidize a series of racemic allylic sec-alcohols into the corresponding α,β-unsaturated ketones. Afterward, these compounds react with different commercially available ene-reductases to afford the corresponding saturated ketones. Remarkably, in the case of trisubstituted alkenes, the bioreduction reaction occurred with high stereoselectivity. Overall, a bienzymatic one-pot two-step sequential strategy has been described with respect to the synthesis of saturated ketones starting from racemic allylic alcohols, thus resembling the metal-catalyzed redox isomerizations of these derivatives that have been previously reported in the literature.

Method for catalyzing aldol condensation reaction by copper salt

The invention discloses a method for catalyzing aldol condensation reaction by copper salt. According to the method, disclosed by the invention, copper halide is used as a catalyst and benzaldehyde and butanone are catalyzed and subjected to the aldol condensation reaction under low-temperature and room-temperature conditions to generate 3-methyl-4-phenyl-3-butene-2-one. The method disclosed by the invention has the advantages of cheap and easy-to-obtain raw materials, moderate conditions, low environment pollution and easiness for separating a product; the utilization of strong-corrosion reagents including hydrochloric acid, sodium hydroxide and the like in present industrial aldol condensation reaction is not utilized and large-scale industrial production is facilitated.

Crystal structures, in-silico study and anti-microbial potential of synthetic monocarbonyl curcuminoids

In this work the screening of 20 unsymmetrical chalcone and curcuminoids analogues in regard of their antimicrobial properties was conducted. Electron donating groups in the aromatic rings in the chalcone and curcuminoid derivatives produced higher antimicrobial effect. Compounds 1, 9 and 15 exhibited good activity against Escherichia coli and Staphylococcus aureus. These compounds were further evaluated against nine micro-organisms of pathological interest. Pharmmaper was used for target fishing of compounds against important bacterial targets. Molecular Docking helped to verify the results of these compounds against the selected bacterial target D-alanyl-D-alanine carboxypeptidase (PDB ID: 1PW1). The crystal structure of ligand and docked conformers in the active site of 1PW1 were analyzed. As a result structure-activity relationships are proposed. Structures of compounds 14 and 16 were obtained through single crystals X-ray diffraction studies. Compound 14 crystallizes in monoclinic space group P21/c with unit cell dimensions a = 13.1293(3) ?, b = 17.5364(4) ?, c = 15.1433(3) ?, β = 95.6440(10), V = 3469.70(13) ?3 and Z = 8. Compound 16 crystallizes in triclinic space group Pī with unit cell dimensions a = 6.8226(4) ?, b = 7.2256(4) ?, c = 18.1235(12) ?, β = 87.322(4), V = 850.57(9) ?3 and Z = 2.

Chemoselective Claisen-Schmidt bis-substitutional condensation catalyzed by an alkoxy-bridged dinuclear Ti(IV) cluster

The highly efficient and chemoselective α,α′-bis-substitution of alkanones is important in organic synthesis. Herein, a dimeric titanium cluster, Ti2Cl2(OPri)6·2HOPri (Ti2), is used in the Claisen-Schmidt condensation reaction, for the selectively activation of symmetrical ketones containing α,α′-methylene groups and production of α,α′-bis-substituted alkanones in high efficiency and chemoselectivity. The high efficiency and chemoselectivity can be extended to a variety of typical alkanones and aromatic aldehydes. Both of the oxo-bridged dimeric motif of Ti2 and the ionic Ti-Cl bond are responsible for the high efficiency and chemoselectivity.

The bioinspired design of a reagent allows the functionalization of Cα-H of α,β-unsaturated carbonyl compounds via the Baylis-Hillman chemistry under ambient conditions

A rationally designed reagent capable of affecting alkylation at Cα of α,β-unsaturated carbonyl compounds is reported. The reaction proceeded at room temperature without any additives. The pH and H-bond formation during the reaction play a key role in the working of the reagent.

Enantiodivergence in the reduction of α-methyl and α-halomethyl enones by microorganisms

Enones (Z)-3-methyl-(Z)-3-chloromethyl- and (Z)-3-bromomethyl-4-R-3-buten- 2-one (R = n-pentyl, phenyl, 2′- and 4′-chlorophenyl, 3′- and 4′-nitrophenyl, 4′-methoxyphenyl) were synthesized and subjected to reduction by the microorganisms Saccharomyces cerevisiae andGeotrichum candidum. Whereas the bioreduction of 3-methy-4-R-3-buten-2-ones afforded the corresponding (S)-4-R-3-methybutan-2-ones, the bioreduction of 3-chloromethyl- and 3-bromomethyl-4-R-3-buten-2-ones afforded the corresponding (R)-4-R-3-methybutan-2-ones.