1865-29-8

Usage

Uses

Used in Flavor and Fragrance Industry:
2-PHENYL-ACRYLIC ACID METHYL ESTER is used as a flavoring agent for its sweet, fruit-like taste, enhancing the taste profiles of various food and beverages. It is also utilized as a fragrance ingredient, adding a pleasant aroma to perfumes, soaps, and cosmetics, where its natural scent is appreciated for creating a fresh and fruity note.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2-PHENYL-ACRYLIC ACID METHYL ESTER is recognized for its potential applications due to its antimicrobial and antioxidant properties. These characteristics make it a candidate for development in treatments and products that require such properties for their efficacy and safety.
While the provided materials do not specify other industries or detailed applications, the above uses are inferred from the general properties and known applications of 2-PHENYL-ACRYLIC ACID METHYL ESTER, or methyl cinnamate, in the industries mentioned. Further research or additional materials would be required to detail more specific applications or industries.

InChI:InChI=1/C10H10O2/c1-8(10(11)12-2)9-6-4-3-5-7-9/h3-7H,1H2,2H3

Upstream product

• 591-50-4 iodobenzene 
• 124582-37-2 methyl 2-(tributylstannanyl)-2-propenoate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 74-88-4 methyl iodide 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 15231-78-4 2.2-dimethyl-5-phenyl-1,3-dioxane-4,6-dione 
• 529-64-6 Tropic acid 
• 616-38-6 carbonic acid dimethyl ester 
• 80-63-7 methyl 2-chloroacrylate 
• 98-80-6 phenylboronic acid 
• 64741-27-1 2,6-bis(diphenylphosphino)pyridine 
• 74-99-7 prop-1-yne 

Downstream Products

• 1528-39-8 3-phenyl-2-pentanone 
• 4842-45-9 1,2,3-triphenylpropan-1-one 
• 723-19-3 cis-1,2-Dimethoxycarbonyl-1-phenylcyclopropane 
• 723-19-3 trans-1,2-Dimethoxycarbonyl-1-phenylcyclopropane 
• 40556-79-4 methyl 2-cyclohexylpropionate 
• 330173-28-9 1-benzyl-3-phenyl-5-(toluene-4-sulfonyl)-piperidine-2,6-dione 
• 459453-61-3 3-[(4-methylphenyl)sulfonyl]-5-phenyl-1-propylpiperidine-2,6-dione 
• 31508-44-8 2-phenylpropionic acid methyl ester 
• 67031-12-3 methyl 4-oxo-2-phenylbutanoate 
• 98324-47-1 2-phenyloxirane-2-carboxylic acid methyl ester 
• 3881-28-5 1-Methyl-3-phenylpiperidin-4-one 
• 137628-75-2 3,5,7-Triphenyl-1-azaadamantan-4,6-dion 
• 53530-59-9 3-Brom-2-hydroxy-2-phenylpropionsaeuremethylester 
• 177581-94-1 methyl 2-phenyl-3-tributyltinpropanate 

Relevant academic research and scientific papers

Rhodium catalysed hydroformylation of unsaturated esters

Rhodium catalysed hydroformylation of unsaturated esters has been studied. A pronounced temperature dependence was observed on the regioselectivity and catalytic activity for these reactions, and under the appropriate conditions, it is possible to obtain preferentially either linear or quaternary products. A quaternary selective hydroformylation of methyl atropate to give 1,3-aldehydic esters has also been developed.

Catalysis in supercritical CO2 using dendrimer-encapsulated palladium nanoparticles

Dendrimer-encapsulated nanoparticles are shown to be versatile catalysts for both the hydrogenation of styrene and Heck heterocoupling of iodobenzene and methacrylate in supercritical CO2 (scCO2).

Group 6 heteroatom- and non-heteroatom-stabilized carbene complexes. β,β′- and α,ββ′-Annulation reactions of cyclic enamines

Cyclization reactions of group 6 Fischer carbene complexes with cyclopentanone and cyclohexanone enamines are described. Enamine 3a undergoes thermal β,β′-annulation with alkenylcarbene complexes 1 and 2 (THF, 60 °C), affording semibullvalenes 5. The metalate intermediates 6, resulting from β,β′-annulation of the enamines 3a and 4a, were quantitatively formed by running the reaction in hexane at room temperature. Acid-promoted demetalation of 6 afforded endo-2-bicyclo[3.2.1]octen-8-ones 7 and endo/exo-2-bicyclo[3.3.1]nonen-9-ones 8 (endo/exo = 5:1). Using (S)-methoxymethylpyrrolidinederived enamines 3b and 4b,c allowed highly enantioenriched cycloadducts endo-(+)-7 as well as endo- (-)-8 and exo-(-)-8 to be accessed. The non -heteroatom -stabilized carbene complex 10 was formed from complex 6 by Me3SiOTf-promoted elimination of the methoxy group, characterized by 13C NMR, and transformed into the organic compounds 7, 7-d, and 11 as well as into bicyclo[3.2.1]octan-2,8-diones 14 and cycloheptanones 15, On the basis of this sequence, enantioenriched cycloheptanones (+)-15 were efficiently prepared in one pot from carbene complexes 2 and enamine 3b (51-55% yield, 91-96% ee). Extension of this work to simple Fischer carbene complexes 16 allowed an appropriate way to generate the nonstabilized pentacarbonyl[(phenyl(alkyl)carbene]tungsten complex 17 to be designed, for which the thermal and chemical behavior leading to compounds 18-21 is described.

Room-temperature Pd-catalyzed methoxycarbonylation of terminal alkynes with high branched selectivity enabled by bisphosphine-picolinamide ligand

We report the room-temperature Pd-catalyzed methoxy-carbonylation with high branched selectivity using a new class of bisphosphine-picolinamide ligands. Systematic optimization of ligand structures and reaction conditions revealed the significance of both

Electrochemical oxidative: Z -selective C(sp2)-H chlorination of acrylamides

An electrochemical method for the oxidative Z-selective C(sp2)-H chlorination of acrylamides has been developed. This catalyst and organic oxidant free method is applicable across various substituted tertiary acrylamides, and provides access to a broad range of synthetically useful Z-β-chloroacrylamides in good yields (22 examples, 73% average yield). The orthogonal derivatization of the products was demonstrated through chemoselective transformations and the electrochemical process was performed on gram scale in flow.

Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates

A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.

Pyrrolidine integrin regulator and application thereof

Disclosed are a compound as represented by formula I, and a racemate, a stereoisomer, a tautomer, an isotopic marker, a nitrogen oxide, a solvate, a polymorph, a metabolite, an ester, and a prodrug thereof or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising same, a preparation method therefor, and the medical use thereof. The structure of formula I is as follows:

Photocatalytic Hydromethylation and Hydroalkylation of Olefins Enabled by Titanium Dioxide Mediated Decarboxylation

A versatile method for the hydromethylation and hydroalkylation of alkenes at room temperature is achieved by using the photooxidative redox capacity of the valence band of anatase titanium dioxide (TiO2). Mechanistic studies support a radical-based mechanism involving the photoexcitation of TiO2 with 390 nm light in the presence of acetic acid and other carboxylic acids to generate methyl and alkyl radicals, respectively, without the need for stoichiometric base. This protocol is accepting of a broad scope of alkene and carboxylic acids, including challenging ones that produce highly reactive primary alkyl radicals and those containing functional groups that are susceptible to nucleophilic substitution such as alkyl halides. This methodology highlights the utility of using heterogeneous semiconductor photocatalysts such as TiO2 for promoting challenging organic syntheses that rely on highly reactive intermediates.

Synergetic Catalysis for One-pot Bis-alkoxycarbonylation of Terminal Alkynes over Pd/Xantphos?Al(OTf)3 Bi-functional Catalytic System

Tandem bis-alkoxycarbonylation of alkynes allows for the preparation of 2-substituted succinates from alkynes and nucleophile alcohol via two successive alkoxycarbonylation with advantages of 100 % atomic economy and simplified one-pot operation. Herein, the one-pot tandem bis-alkoxycarbonylation of alkynes was accomplished over the bi-functional catalytic system containing Xantphos-modified Pd-complex and Lewis super-acid of Al(OTf)3. It was found that, via the synergetic catalysis, the involved Xantphos-modified Pd-complex was responsible for the activation of CO and the alkynes through coordination to Pd-center while Al(OTf)3 was in charge of the activation of the alcohol to facilitate the formation of [Pd?H]+ active species. The in situ high-pressure FT-IR analysis, coupled with 1H/13C NMR spectral characterizations, confirmed that the introduced Al(OTf)3 with intensive oxophilicity (via acid-base pair interaction) was able to activate nucleophilic MeOH to be a reliable proton-donor (i. e. hydride-source) to warrant the formation and stability of [Pd?H]+ species upon the oxidation of Pd0 by H+ (Pd0+H+→[PdII?H]+). Over the developed bi-functional catalytic system, the yields of the target diesters were obtained in the range of 36～86 % in this sequence with the wide substrate scope.

Palladium-catalyzed intermolecular C-H silylation initiated by aminopalladation

A Pd(ii)-catalyzed intermolecular C-H silylation reaction initiated by aminopalladation has been developed. The C-H bonds were activated by an alkyl Pd(ii) species generated through aminopalladation and then disilylated with hexamethyldisilane to form disilylated indolines as the final products. The reaction provides a new method for the introduction of silyl groups into complex organic molecules.