5747-06-8

Usage

Uses

Used in Organic Synthesis:
4-Phenyl-4-Pentenoic Acid is used as a key intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows for versatile reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Phenyl-4-Pentenoic Acid is used as a building block for the development of new drugs. Its potential biological activities have been studied, and it is considered a promising candidate for the treatment of various diseases.
Used as a Flavoring Agent:
4-Phenyl-4-Pentenoic Acid is used as a flavoring agent in the food and beverage industry. Its unique chemical structure contributes to the development of distinct flavors and scents, enhancing the sensory experience of various products.
Used in Polymer Synthesis:
In the polymer industry, 4-Phenyl-4-Pentenoic Acid is utilized in the synthesis of polymers with specific properties. Its incorporation into polymer chains can lead to materials with tailored characteristics, such as improved strength, flexibility, or thermal stability.
Used as a Precursor in Compound Production:
4-Phenyl-4-Pentenoic Acid serves as a precursor in the production of various compounds, including specialty chemicals and materials. Its reactivity and structural features make it an essential component in the synthesis of these advanced materials.

Upstream product

• 78687-92-0 ethyl 4-phenyl-4-pentenoate 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 2051-95-8 succinylbenzene 
• 93863-05-9 4-phenylpent-4-enoic acid methyl ester 
• 4432-63-7 2-phenylacrolein 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 108-30-5 succinic acid anhydride 
• 71-43-2 benzene 
• 596-43-0 bromo-triphenyl-methane 
• 27200-84-6 methyl triphenylphosphonium bromide 
• 6270-17-3 ethyl 3-benzoylpropanoate 
• 100-59-4 phenylmagnesium chloride 
• 194805-62-4 methyl-4-bromo-pent-4-enoate 

Downstream Products

• 7210-42-6 (5S)-5-methyl-5-phenyldihydrofuran-2(3H)-one 
• 88314-79-8 (R)-5-methyl-5-phenyl-3,4-dihydro(5H)-furan-2-one 
• 3183-15-1 4-oxo-5-phenylvaleric acid 
• 1254701-62-6 (S)-5-(bromomethyl)-dihydro-5-phenylfuran-2(3H)-one 
• 1217263-84-7 (R)-5-(bromomethyl)-dihydro-5-phenylfuran-2(3H)-one 
• 1217263-86-9 (S)-5-(chloromethyl)-5-phenyldihydrofuran-2(3H)-one 
• 1217263-85-8 (R)-5-(chloromethyl)-5-phenyldihydrofuran-2(3H)-one 
• 1338575-99-7 4-nitro-N-((2-phenyltetrahydrofuran-2-yl)methyl)benzenesulfonamide 
• 1338575-94-2 tert-butyl (3-phenylbut-3-en-1-yl)carbamate 

Relevant academic research and scientific papers

Quaternary Charge-Transfer Complex Enables Photoenzymatic Intermolecular Hydroalkylation of Olefins

Intermolecular C-C bond-forming reactions are underdeveloped transformations in the field of biocatalysis. Here we report a photoenzymatic intermolecular hydroalkylation of olefins catalyzed by flavin-dependent 'ene'-reductases. Radical initiation occurs via photoexcitation of a rare high-order enzyme-templated charge-transfer complex that forms between an alkene, α-chloroamide, and flavin hydroquinone. This unique mechanism ensures that radical formation only occurs when both substrates are present within the protein active site. This active site can control the radical terminating hydrogen atom transfer, enabling the synthesis of enantioenriched γ-stereogenic amides. This work highlights the potential for photoenzymatic catalysis to enable new biocatalytic transformations via previously unknown electron transfer mechanisms.

Are bis(pyridine)iodine(i) complexes applicable for asymmetric halogenation?

Enantiopure halogenated molecules are of tremendous importance as synthetic intermediates in the construction of pharmaceuticals, fragrances, flavours, natural products, pesticides, and functional materials. Enantioselective halofunctionalizations remain

Development of Nitrolactonization Mediated by Iron(III) Nitrate Nonahydrate

The nitrolactonization of alkenyl carboxylic acids mediated by Fe(NO3)3·9H2O has been developed. Nitrolactones were obtained in up to 93% yield by treatment of alkenyl carboxylic acids with Fe(NO3)3·9H2O. Mechanistic studies disclosed that the reaction proceeded through a radical intermediate generated from addition of NO2 to alkenyl carboxylic acids.

Metal-Free Arylation-Lactonization Sequence of γ-Alkenoic Acids Using Anilines as Aryl Radical Precursors

The presence of salicylic acid (10 mol-%) and H2O (10 equiv.) significantly improves the arylation-lactonization sequence of γ-alkenoic acids with in situ formed diazonium salts (from bench stable anilines). The reaction is finished in less than 5 h without thermal or photochemical activation, giving access to a variety of γ,γ-disubstituted butyrolactones. The protocol is user-friendly and can be used at gram-scale or adapted to transform alkenols into phthalanes. Control experiments revealed that aryl radicals participate in the reaction and a plausible mechanism is proposed to include this and other mechanistic investigations, for the catalyzed and the background reaction.

Synthesis of Novel C 2-Symmetric Sulfur-Based Catalysts: Asymmetric Formation of Halo- and Seleno-Functionalized Normal- and Medium-Sized Rings

The synthesis of novel, highly functionalized, C 2 -symmetric sulfur-based catalysts is developed and their catalytic applications are explored in asymmetric bromo-, iodo- and seleno-functionalizations of alkenoic acids. This protocol provides

Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis

The double functionalization of styrenes through Cu-mediated assisted tandem catalysis was developed. The reaction was initiated by Cu-catalyzed aziridination and the subsequent nucleophilic ring-opening, which was triggered by the addition of (NH4)2S2O8 as an oxidant of Cu-catalyst to form a variety of C–C and C–X bonds. The expansion to three contiguous catalytic cycles led to the synthesis of functionalized indolines by one-pot operation.

Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons

Copper-catalyzed alkene amino oxygenation reactions using O-acylhydroxylamines have been achieved for a rapid and modular access to diverse 1,2-amino oxygen-containing molecules. This transformation is applicable to the use of alcohols, carbonyls, oximes, and thio-carboxylic acids as nucleophiles on both terminal and internal alkenes. Mild reaction conditions tolerate a wide range of functional groups, including ether, ester, amide, carbamate, and halide. The reaction protocol allows for starting with free amines as the precursor of O-benzoylhydroxylamines to eliminate their isolation and purification, contributing to broader synthetic utilities. Mechanistic investigations reveal the amino oxygenation reactions may involve distinct pathways, depending on different oxygen nucleophiles.

Enantioselective Halo-oxy- and Halo-azacyclizations Induced by Chiral Amidophosphate Catalysts and Halo-Lewis Acids

Catalytic enantioselective halocyclization of 2-alkenylphenols and enamides have been achieved through the use of chiral amidophosphate catalysts and halo-Lewis acids. Density functional theory calculations suggested that the Lewis basicity of the catalyst played an important role in the reactivity and enantioselectivity. The resulting chiral halogenated chromans can be transformed to α-Tocopherol, α-Tocotrienol, Daedalin A and Englitazone in short steps. Furthermore, a halogenated product with an unsaturated side chain may provide polycyclic adducts under radical cyclization conditions.

Gold(I)-Catalyzed Enantioselective Annulations between Allenes and Alkene-Tethered Oxime Ethers: A Straight Entry to Highly Substituted Piperidines and aza-Bridged Medium-Sized Carbocycles

Piperidine scaffolds are present in a wide range of bioactive natural products and are therefore considered as highly valuable, privileged synthetic targets. In this manuscript, we describe a gold-catalyzed annulation strategy that allows a straightforward assembly of piperidines and piperidine-containing aza-bridged products from readily available alkene-tethered oxime ethers (or esters) and N-allenamides. Importantly, we demonstrate the advantages of using oxime derivatives over imines, something pertinent to the whole area of gold catalysis, and provide relevant mechanistic experiments that shed light into the factors affecting the annulation processes. Moreover, we also describe preliminary experiments demonstrating the viability of enantioselective versions of the above reactions.

Synthesis of Chiral Sulfonyl Lactones via Copper-Catalyzed Asymmetric Radical Reaction of DABCO?(SO2)

In the present work, an asymmetric copper-catalyzed radical multi-component cascade reaction of an unsaturated carboxylic acid, aryldiazonium tetrafluoroborate, and DABCO?(SO2)2 (DABSO) has been developed for the enantioselective synthesis of sulfonyl lactones. In this reaction, this SO2 surrogate, DABSO was applied for the first time in the construction of chiral compounds. This multiple-step asymmetric radical reaction was carried out under mild conditions and tolerated a wide range of substrates, resulting in the corresponding sulfonyl lactones with up to 95% chemical yields and 88% ee. The current reaction enriches the research contents of DABSO, and provides a new and efficient strategy to chiral functionalized lactones bearing quarternary stereogenic center. (Figure presented.).