42968-14-9

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Buten-2-one, 3-methyl-4-phenyl-, (3E)is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows for the development of new drugs with potential therapeutic benefits.
Used in Flavoring Agents for the Food Industry:
3-Buten-2-one,3-methyl-4-phenyl-, (3E)is employed as a flavoring agent in the food industry, adding a sweet and floral taste to various food products. Its strong aroma and solubility in organic solvents make it an ideal choice for enhancing the flavor profile of different food items.
Used in Perfume Production:
3-Buten-2-one, 3-methyl-4-phenyl-, (3E)serves as an intermediate in the production of perfumes and other aromatic products. Its strong, sweet, and floral scent contributes to the creation of unique and appealing fragrances.
Used in Material Science:
This chemical has been studied for its potential applications in the field of material science. Its unique properties may contribute to the development of new materials with specific characteristics, such as improved strength, flexibility, or other desirable attributes.

Upstream product

• 100-52-7 benzaldehyde 
• 78-93-3 butanone 
• 673-32-5 1-Phenylprop-1-yne 
• 75-05-8 acetonitrile 
• 87422-10-4 (E)-3-methyl-4-phenyl-but-3-en-2-ol 
• 57-15-8 1,1,1-trichloro-2-methyl-2-propanol 
• 4091-39-8 3-chloro-2-butanone 
• 814-75-5 3-bromo-butanone 
• 1895-97-2 2-methyl-3-phenylacrylic acid 
• 917-54-4 methyllithium 
• 399513-43-0 (+/-)-(1E)-2-(1-methyl-2-phenyl-vinyl)-oxirane 
• 7042-33-3 ethyl (E)-2-methyl-3-phenyl-2-propenoate 
• 67-68-5 dimethyl sulfoxide 
• 122-57-6 1-Phenylbut-1-en-3-one 

Downstream Products

• 102077-57-6 2-methyl-1t,7t-diphenyl-hepta-1,4t,6-trien-3-one 
• 14164-67-1 2-methyl-1,5-diphenyl-penta-1,4-dien-3-one 
• 72885-62-2 3-methyl-4t-phenyl-but-3-en-2-one-(2,4-dinitro-phenylhydrazone) 
• 89882-20-2 (RR,SS)-3-methyl-4-dimethyl(phenyl)silyl-4-phenylbutan-2-one 
• 89882-20-2 (RS,SR)-3-methyl-4-dimethyl(phenyl)silyl-4-phenylbutan-2-one 
• 2550-27-8 (3S)-3-methyl-4-phenylbutan-2-one 
• 2550-27-8 (2R)-3-methyl-4-phenylbutan-2-one 
• 76888-39-6 (+)-3-methyl-4-phenyl-3(E)-buten-2-ol 
• 76888-39-6 (E)-3-methyl-4-phenylbut-3-en-2-ol 
• 174848-61-4 (E)-(R)-3-methyl-4-phenylbut-3-en-2-ol 
• 156047-69-7 3-Hydroxy-3-((E)-3-methyl-2-oxo-4-phenyl-but-3-enyl)-1,3-dihydro-indol-2-one 
• 56836-93-2 3-methyl-4-phenylbutan-2-ol 
• 30625-97-9 (E)-(2,3-dimethylbuta-1,3-dien-1-yl)benzene 

Relevant academic research and scientific papers

Stereoselective Iridium-N,P-Catalyzed Double Hydrogenation of Conjugated Enones to Saturated Alcohols

Asymmetric hydrogenation of prochiral substrates such as ketones and olefins constitutes an important instrument for the construction of stereogenic centers, and a multitude of catalytic systems have been developed for this purpose. However, due to the different nature of the π-system, the hydrogenation of olefins and ketones is normally catalyzed by different metal complexes. Herein, a study on the effect of additives on the Ir-N,P-catalyzed hydrogenation of enones is described. The combination of benzamide and the development of a reactive catalyst unlocked a novel reactivity mode of Crabtree-type complexes toward C=O bond hydrogenation. The role of benzamide is suggested to extend the lifetime of the dihydridic iridium intermediate, which is prone to undergo irreversible trimerization, deactivating the catalyst. This unique reactivity is then coupled with C=C bond hydrogenation for the facile installation of two contiguous stereogenic centers in high yield and stereoselectivity (up to 99% ee, 99/1 d.r.) resulting in a highly stereoselective reduction of enones.

Highly Active Cooperative Lewis Acid—Ammonium Salt Catalyst for the Enantioselective Hydroboration of Ketones

Enantiopure secondary alcohols are fundamental high-value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15 400), which were increased by around 1.5–3 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxophilic Lewis acid within the same catalyst molecule. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an SN2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working.

Hydroperoxidations of Alkenes using Cobalt Picolinate Catalysts

Hydroperoxides were synthesized in one step from various alkenes using Co(pic)2as the catalyst with molecular oxygen and tetramethyldisiloxane (TMDSO). The hydration product could be obtained using a modified catalyst, Co(3-mepic)2, with molecular oxygen and phenylsilane. Formation of hydroperoxides occurred through a rapid Co-O bond metathesis of a peroxycobalt compound with isopropanol.

Method for hydrocarbylation synthesis of trisubstituted and tetrasubstituted olefins from non-terminal olefins

The invention discloses a method for hydrocarbylation synthesis of trisubstituted and tetrasubstituted olefins from non-terminal olefins, wherein the method comprises the steps: carrying out hydrocarbylation reaction on the non-terminal olefins and sulfoxide in the presence of ferric salt and hydrogen peroxide, carrying out one-pot reaction on disubstituted non-terminal olefins to generate the trisubstituted olefins, and carrying out one-pot reaction on the trisubstituted non-terminal olefins to generate the tetrasubstituted olefins. In the method, sulfoxide is simultaneously used as a hydrocarbylation reagent and a solvent of olefins, and one more hydrocarbyl substituent is added to a reaction product compared with a double-bond carbon atom of a reactant, so that an olefin carbon chain isincreased; the reaction conditions are mild, the selectivity is good, the yield is high, and industrial production is facilitated.

Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones

Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.

Method for synthesizing alkyl olefin through coupling of double-bond carbon-hydrogen bond and saturated carbon-hydrogen bond

The invention discloses a method for synthesizing alkyl olefin through coupling of a double-bond carbon-hydrogen bond and a saturated carbon-hydrogen bond. According to to the method, one-pot reactionis implemented on olefin and sulfoxide in the presence of ferric salt and hydrogen peroxide to generate alkyl olefin; in the method, sulfoxide is simultaneously used as a hydrocarbylation reagent anda solvent of olefin, and a reaction product is alkyl olefin from sulfoxide alkyl coupled with olefin carbon atoms, so that an olefin carbon chain is increased; the reaction conditions are mild, the selectivity is good, the yield is high, and industrial production is facilitated.

Capturing the Monomeric (L)CuH in NHC-Capped Cyclodextrin: Cavity-Controlled Chemoselective Hydrosilylation of α,β-Unsaturated Ketones

The encapsulation of copper inside a cyclodextrin capped with an N-heterocyclic carbene (ICyD) allowed both to catch the elusive monomeric (L)CuH and a cavity-controlled chemoselective copper-catalyzed hydrosilylation of α,β-unsaturated ketones. Remarkably, (α-ICyD)CuCl promoted the 1,2-addition exclusively, while (β-ICyD)CuCl produced the fully reduced product. The chemoselectivity is controlled by the size of the cavity and weak interactions between the substrate and internal C?H bonds of the cyclodextrin.

Thermal decarboxylative Nazarov cyclization of cyclic enol carbonates involving chirality transfer

Decarboxylative Nazarov cyclization of chiral cyclic enol carbonates proceeded to afford chiral 2-cyclopentenones with excellent chirality transfer under thermal conditions without any catalyst. Interestingly, the thermal decarboxylative Nazarov cyclization furnished the desired product with better chirality transfer than the Lewis acid-catalyzed reaction.

Bovine serum albumin-catalysed cross aldol condensation: Influence of ketone structure

Bovine serum albumin (BSA) catalyses the cross aldol condensation and proved to be catalytically active at mild temperature and in ethanol, a cheap and green solvent, contrasting with the strong or expensive reaction media usually employed for this reaction. We herein report the reaction of a set of ketones (butanone, 3-pentanone, cyclopentanone and cyclohexanone) with benzaldehyde and p-nitrobenzaldehyde which provided high conversions (77–95%) of the corresponding enones (isolated in a range of yields from 19% to 74%). Parameters assayed to achieve these conversion values were solvent, ketone/aldehyde molar ratio and temperature. In this procedure only cyclohexanone gave the bis-enone, by-product of the conventional aldol condensation, in low amount even at high benzaldehyde/cyclohexanone molar excess. Under the assayed conditions null or low ketol amounts were observed, except for the reaction of cyclopentanone and p-nitrobenzaldehyde. Moreover, kinetic data of BSA-catalysed aldol condensation of cyclohexanone and p-nitrobenzaldehyde suggest an ordered bi bi mechanism for enone formation; an enamine mechanism involving residues of the catalytic cavity exhibiting abnormal pKa values is also proposed.

Decarboxylative Nazarov Cyclization-Based Chirality Transfer for Asymmetric Synthesis of 2-Cyclopentenones

Asymmetric synthesis of 2-cyclopentenones was achieved by chirality transfer based on Lewis acid catalyzed decarboxylative Nazarov cyclization of optically active cyclic enol carbonates, which are prepared by silver-catalyzed carbon dioxide incorporation into optically pure propargyl alcohols. The stereochemistry at the 4,5-positions of the 2-cyclopentenones was cleanly constructed by reflecting the stereochemistry of the starting materials. This method could be applied to various substrates to obtain the corresponding products in high yields with highly efficient chirality transfer.