4439-87-6

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenyllevulinic acid is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs and materials, enhancing the industry's capacity to innovate and provide novel therapeutic options.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Phenyllevulinic acid is utilized as an intermediate in the production of agrochemicals, potentially contributing to the development of more effective and environmentally friendly products for agricultural applications.
Used in Flavor and Fragrance Industry:
2-Phenyllevulinic acid is employed as a building block in the creation of natural and artificial flavors and fragrances, adding to the diversity and complexity of scents and tastes in various consumer products.
Used in Cancer Treatment:
2-Phenyllevulinic acid is used as a potential therapeutic agent in cancer treatment, leveraging its properties to target and combat cancer cells, offering a novel approach to managing this disease.
Used as an Antioxidant:
In various applications, 2-Phenyllevulinic acid serves as an antioxidant, providing protection against oxidative stress and potentially contributing to the prevention of certain diseases and the preservation of product integrity.

InChI:InChI=1/C11H12O3/c1-8(12)7-10(11(13)14)9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,13,14)

Upstream product

• 620-80-4 ethyl 2-benzylidene acetoacetate 
• 90124-76-8 2-acetyl-3-phenyl-succinic acid diethyl ester 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 74-88-4 methyl iodide 
• 124-38-9 carbon dioxide 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 4743-82-2 4-oxo-2-pentenoic acid 
• 71-43-2 benzene 
• 51632-38-3 2-phenyl-pent-4-ynoic acid 
• 110698-36-7 2-nitro-5-oxo-3-phenylhexanoic acid ethyl ester 
• 106180-81-8 2,2-Dimethoxy-5-methyl-3-phenyl-2,3-dihydrofuran 
• 13049-41-7 1,1-dimethoxy-2-phenylethene 
• 101-41-7 benzeneacetic acid methyl ester 

Downstream Products

• 40923-67-9 5-methyl-3-phenyldihydrofuran-2(3H)-one 
• 55091-68-4 3-phenyl-5-methyl-2,5-dihydrofuran-2-one 
• 21053-95-2 γ-methyl-α-phenyltetronic acid 
• 20272-25-7 cis-4-methyl-2-phenyl-γ-butyrolactone 
• 20272-25-7 trans-4-methyl-2-phenyl-γ-butyrolactone 
• 6303-83-9 ethyl 4-oxo-2-phenylpentanoate 
• 95605-88-2 4,5-Dihydro-4-phenyl-6(α-p-methoxystyryl)pyridazin-3(2H)-one 
• 95605-91-7 4-phenyl-6-(α-p-methoxystyryl)pyridazin-3(2H)-one 
• 95605-87-1 4,5-dihydro-4-phenyl-6(α-styryl)pyridazin-3(2H)-one 
• 95605-90-6 4-phenyl-6-(α-styryl)pyridazin-3(2H)-one 
• 138984-15-3 1-(2-Oxo-propyl)-indan-2-one 
• 116145-09-6 7-Methyl-5-phenyl-indan-4-ol 
• 95605-95-1 δ-(p-methoxyphenyl)-methylene-α-phenylleavulinic acid 
• 95605-94-0 δ-phenylmethylene-α-phenylleavulinic acid 

Relevant academic research and scientific papers

Bimetallic Phase Transfer Catalysis

γ-Keto acids are obtained by the phase transfer catalysed reaction of alkynes with carbon monoxide and methyl iodide in the presence of catalytic amounts of cobalt and ruthenium carbonyl complexes.

Practical synthesis of diethyl phenylsuccinate by Mg-promoted carboxylation of ethyl cinnamate

Mg-promoted reduction of ethyl cinnamate (1a) in the presence of carbon dioxide gave a mixture of β-carboxylated compound 2a and α,β-dicarboxylated compound 3a. Similar reductive carboxylation of 1a followed by acidic decarboxylation of one of the two geminal carboxyl groups of the generated 3a and esterification afforded selective formation of diethyl phenylsuccinate (2a) in good yield.

Formation of γ-oxoacids and 1 H-pyrrol-2(5 H)-ones from α,β-unsaturated ketones and ethyl nitroacetate

Michael addition of ethyl nitroacetate on α,β-unsaturated ketones followed by Nef oxidation under hydrolytic conditions yields γ-oxoacids instead of the corresponding α,δ-dioxoesters. A concerted decarboxylation step is proposed on the basis of computational results. Finally, conversion of the γ-ketoacids thus prepared into 1H-pyrrol-2(5H)-ones by reaction with primary amines under Paal-Knorr conditions is also reported.

Au2O3 as a stable and efficient catalyst for the selective cycloisomerization of γ-acetylenic carboxylic acids to γ-alkylidene-γ-butyrolactones

The high potential of commercially available Au2O3 as a catalyst in the cyclization of alkynes bearing carboxylic acids to the corresponding γ-alkylidene-γ-butyrolactones through a general, efficient and easy procedure is presented. The reaction shows a high degree of chemo-, regio-, and stereoselectivity. The 5-exo mode of cyclization and anti auration are a general trend for the Au2O3 catalyst. Georg Thieme Verlag Stuttgart.

Predominant 1,2-insertion of styrene in the Pd-catalyzed alternating copolymerization with carbon monoxide

The regioselectivity of styrene insertion to an acyl-Pd bond was studied by NMR in (i) a stoichiomeric reaction and (ii) a copolymerization with CO. In the stoichiometric reaction of styrene with [(CH3CO)Pd-(CH3CN){(R,S)-BINAPHOS}] ·[B{3,5-(CF3)2C6 H3}4], both 1,2-and 2,1-products were given. To mimic the real polymerization conditions, a polyketone-substituted complex [{CH3(CH2CHCH3CO)n}Pd{(R,S)-BINAP HOS}]·[B(3,5-(CF3)2C6 H3)4] (n ≈ 14) was prepared. When this polymer-attached Pd species was treated with styrene, the 1,2-insertion product was the only detectable species. Thus, exclusive 1,2-insertion is demonstrated to be responsible for the styrene-CO copolymerization, in sharp contrast to the predominant 2,1-insertion with conventional nitrogen ligands. Chain-end analysis revealed that β-hydride elimination took place from the 2,1-complex but not from the 1,2-complex. Thus, once 2,1-insertion occurs, rapid β-hydride elimination proceeds to terminate the polymerization, as is common to the other phosphorus-ligand systems. The resulting Pd-H species re-initiates the copolymerization, as was proven by MALDI-TOF mass analysis of the product copolymers.

Chemoselectivity of rhodium carbenoids. A comparison of the selectivity for O-H insertion reactions or carbonyl ylide formation versus aliphatic and aromatic C-H insertion and cyclopropanation

A range of diazocarbonyl compounds 1-9 containing two different functional groups has been prepared, and their rhodium(II) catalysed decomposition studied as a means of probing the chemoselectivity of carbenoid intermediates. The results indicate that wereas O-H insertion reactions predominate over cyclopropanation and aromatic insertion reactions, carbonyl ylide formation vs other competing processes is more finely balanced, and is catalyst dependent.

A new chiral alkylation methodology for the synthesis of 2-alkyl-4-ketoacids in high optical purity using 2-triflyloxy esters

Optical active 2-triflyloxy esters are excellent alkylating agents for β-ketoester enolates. Decarboxylation of the alkylation products gives 2-substituted-4-ketoacid derivatives in high optical purities.

Electrocarboxylation de composes carbonyles aliphatiques, aromatiques et vinyliques: interet de l'utilisation d'une anode consommable en magnesium

In the presence of carbon dioxide in DMF, the electroreduction of carbonyl compounds or α,β-ketoalkenes at high concentration yields respectively α-hydroxyacids and β-ketoacids.The use of a sacrificial magnesium anode allows constant current electrolyses in a diaphragmless cell.

Reactions of Ketenes. XX. Phenylketene Dimethylacetal As Synthon For the Introduction of Functionalized Phenylethyl Units

Phenylketene dimethylacetal (1) reacts with the α-diazoketones to give the dihydrofurans 6.These compounds, as cyclic ortho esters, can undergo dealcoholation into the furans 2 and hydrolysis into the γ-ketoesters 3 and into the γ-ketoacids 4.Cyclopropane acetal 8, obtained starting from acetal 1 and ethyl diazoacetate, by heating leads quantitatively to functionalized ester 9.These synthetic methods enlarge the sphere of applicability of the electron-rich alkene 1 as synthon in organic synthesis.

ELECTROCHEMICAL CARBOXYLATION OF alpha , beta -UNSATURATED KETONES WITH CARBON DIOXIDE.

Several aromatic and aliphatic alpha , beta -unsaturated ketones were converted to the corresponding gamma -keto acids by the electrochemical reduction in acetonitrile in the presence of CO//2. The yields of the keto acid were 73-82% when the enones have at least one aromatic substituent. In the case of aliphatic enones, the yields of the carboxylation reaction were 67% for 2-cyclohexen-1-one and 44% for 3-buten-2-one.