55282-95-6

Usage

Uses

Used in Flavoring Agents:
(2E)-5-Phenyl-2-pentenoic acid ethyl ester is used as a flavoring agent in the food industry for its sweet, fruity odor. It enhances the taste and aroma of food products, providing a pleasant sensory experience for consumers.
Used in Perfume and Fragrance Industry:
In the perfume and fragrance industry, (2E)-5-Phenyl-2-pentenoic acid ethyl ester is used as a key ingredient to create a variety of scents. Its floral and fruity notes contribute to the overall composition of perfumes, colognes, and other fragranced products, adding depth and complexity to the scent profile.
Used in Organic Synthesis:
(2E)-5-Phenyl-2-pentenoic acid ethyl ester is also utilized in the synthesis of other organic compounds. Its unique chemical structure allows it to be a valuable building block in the creation of various chemical products, including pharmaceuticals and other specialty chemicals.
Used in Pharmaceutical Formulations:
(2E)-5-Phenyl-2-pentenoic acid ethyl ester can be found in some pharmaceutical formulations, where it may serve as an active ingredient or a component in the development of new drugs. Its versatility in chemical reactions and potential therapeutic properties make it a candidate for further exploration in the pharmaceutical industry.

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 121192-49-2 P--P,P-diphenyl-P-methylphosphonium trifluoromethanesulfonate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 100-52-7 benzaldehyde 
• 623-73-4 diazoacetic acid ethyl ester 
• 250607-16-0 3-(1'-hydroxy-3'-phenylpropyl)-5,5-dimethyloxazolidin-2-one 
• 122-97-4 3-Phenyl-1-propanol 
• 250607-11-5 3-(3'-phenylpropionyl)-5,5-dimethyloxazolidin-2-one 
• 13950-58-8 ethyl 2-(triphenylsilyl)acetate 
• 16139-79-0 ethyl diphenylphosphonoacetate 
• 64-17-5 ethanol 
• 24271-22-5 5-phenyl-2(E)-pentenoic acid 
• 24074-26-8 ethyl (diisopropylphosphoryl)acetate 

Downstream Products

• 79424-79-6 (2S,3S)-2-Chloro-3-hydroxy-5-phenyl-pentanoic acid ethyl ester 
• 10521-91-2 5-phenylpentan-1-ol 
• 36884-28-3 5-phenyl-1-pentanal 
• 75553-28-5 Essigsaeure-(5-phenylpentyl)ester 
• 1198356-01-2 (R)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-phenylpentanoate 
• 1067197-74-3 (E)-1-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphorinan-2-yl)-6-phenylhex-3-en-2-one 
• 1452139-53-5 (E)-1,7-diphenylhept-4-en-1-one 
• 1452139-57-9 (E)-5-phenyl-2-[3-phenylprop-1-en-1-yl]-3,4-dihydro-2H-pyrrole 
• 1452139-59-1 2-phenyl-5-(3-phenylpropyl)-1H-pyrrole 
• 477531-94-5 (2E,4E)-ethyl 7-phenylhepta-2,4-dienoate 
• 10576-66-6 (2E,4E)-7-phenylhepta-2,4-dienal 

Relevant academic research and scientific papers

One-pot chemoenzymatic reactions in water enabled by micellar encapsulation

The use of micellar conditions to enable one-pot reactions involving both transition metal and enzymatic catalysts is reported. Representative enzymatic transformations under micellar conditions are unaffected by the presence of non-ionic surfactants, including designer surfactants such as TPGS-750-M. Furthermore, the presence of enzymes has a negligible effect on transition metal catalysis under micellar conditions in water. Finally, three one-pot chemoenzymatic reactions in water are reported in which the micelle-forming surfactant TPGS-750-M is a crucial factor for reaction efficiency.

A Sequential Acyl Thiol-Ene and Thiolactonization Approach for the Synthesis of δ-Thiolactones

A novel strategy for the synthesis of δ-thiolactones from inexpensive and readily available ?-unsaturated esters has been developed. This strategy incorporates a radical acyl thiol-ene reaction as the key C-S bond forming step. Cyclization is achieved via a Steglich-type thiolactonization of 5-mercaptopentanoic acids. We report the facile and scalable synthesis of δ-thiolactones in moderate to good yield under mild reaction conditions with tolerance for a range of functional groups.

Copper-Catalyzed Perfluoroalkylation of Allyl Phosphates with Stable Perfluoroalkylzinc Reagents

A general and practical method for copper-catalyzed cross-coupling of allyl phosphates with stable perfluoroalkylzinc reagents has been developed. The reaction proceeds under mild reaction conditions with high efficiency, good functional group tolerance, and high regio- A nd stereoselectivities and provides general, straightforward, and useful access to allyl-perfluoroalkyl compounds. Preliminary mechanistic studies reveal that the allyl copper intermediate may be involved in the catalytic cycle.

Catalytic hydrogenation of α,β-unsaturated carboxylic acid derivatives using copper(i)/N-heterocyclic carbene complexes

A simple and air-stable copper(i)/N-heterocyclic carbene complex enables the catalytic hydrogenation of enoates and enamides, hitherto unreactive substrates employing homogeneous copper catalysis and H2 as a terminal reducing agent. This atom economic transformation replaces commonly employed hydrosilanes and can also be carried out in an asymmetric fashion.

Multicatalytic Stereoselective Synthesis of Highly Substituted Alkenes by Sequential Isomerization/Cross-Coupling Reactions

Starting from readily available alkenyl methyl ethers, the stereoselective preparation of highly substituted alkenes by two complementary multicatalytic sequential isomerization/cross-coupling sequences is described. Both elementary steps of these sequences are challenging processes when considered independently. A cationic iridium catalyst was identified for the stereoselective isomerization of allyl methyl ethers and was found to be compatible with a nickel catalyst for the subsequent cross-coupling of the in situ generated methyl vinyl ethers with various Grignard reagents. The method is compatible with sensitive functional groups and a multitude of olefinic substitution patterns to deliver products with high control of the newly generated C=C bond. A highly enantioselective variant of this [Ir/Ni] sequence has been established using a chiral iridium precatalyst. A complementary [Pd/Ni] catalytic sequence has been optimized for alkenyl methyl ethers with a remote C=C bond. The final alkenes were isolated with a lower level of stereocontrol. Upon proper choice of the Grignard reagent, we demonstrated that C(sp2) - C(sp2) and C(sp2) - C(sp3) bonds can be constructed with both systems delivering products that would be difficult to access by conventional methods.

Radical-mediated reactions of α-bromo aluminium thioacetals, α-bromothioesters, and xanthates for thiolactone synthesis

Thiolactones have attracted considerable attention in recent years as bioactive natural products, lead compounds for drug discovery, molecular probes, and reagents for polymerisation. We have investigated radical-mediated C-C bond forming reactions as a s

Remote sp3 C–H Amination of Alkenes with Nitroarenes

Direct installation of a functional group at remote, unfunctionalized sites in an alkyl chain is a synthetically valuable but rarely reported process. The remote relay hydroarylamination of distal and proximal olefins, and of olefin isomeric mixtures, has been achieved through NiH-catalyzed alkene isomerization and sequential reductive hydroarylamination with nitroarenes. This provides an attractive approach to the direct installation of a distal arylamino group within alkyl chains. The single-step conversion of simple olefins and nitro(hetero)arenes to value-added arylamines is a practical strategy for amine synthesis as well as the remote activation of sp3 C–H bonds. The value of this transformation is further supported by the regioconvergent arylamination of isomeric mixtures of olefins. Modern organic synthesis requires more efficient strategies, such as C–H functionalization, with which to construct complex molecules from readily available chemicals. Undirected functionalization of remote aliphatic C–H bonds is a synthetically valuable but largely unknown process. Synergistic combination of metal-catalyzed chainwalking (migration of a double bond along the hydrocarbon chain, a process involving repeated migratory insertions and β-hydride eliminations) and cross-coupling chemistry offers a general approach to the remote functionalization of easily accessed unsaturated hydrocarbon substrates. In this paper, we demonstrate that direct installation of a distal arylamino group can be achieved from two common feedstock chemicals (olefins and nitroarenes) via nickel hydride chemistry. It is anticipated that the strategy could inspire the development of other remote functionalizations with different regioselectivity as well as asymmetric transformations. Zhu and colleagues describe the remote hydroamination of alkenes with nitro(hetero)arenes through nickel-catalyzed alkene isomerization and sequential reductive relay hydroamination process. Using two common feedstock chemicals, olefins and nitroaromatics, in an operationally simple procedure, this attractive protocol provides efficient and practical access to a wide range of arylamines under mild conditions.

Stereodivergence in the Ireland-Claisen Rearrangement of α-Alkoxy Esters

A systematic investigation into the Ireland-Claisen rearrangement of α-alkoxy esters is reported. In all cases, the use of KN(SiMe3)2 in toluene gave rearrangement products corresponding to a Z-enolate intermediate with excellent diastereoselectivity, presumably because of chelation control. On the other hand, chelation-controlled enolate formation could be overcome for most substrates through the use of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).

One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts

A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O 2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO 2 Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.

Facile synthesis of α, β-unsaturated esters through a one-pot copper-catalyzed aerobic oxidation-Wittig reaction

An efficient one-pot synthesis of α, β-unsaturated esters through the aerobic oxidation – Wittig tandem reaction of alcohols and phosphorous ylide is developed. This new method operates under mild reaction conditions, and uses CuI/TEMPO (TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) as co-catalyst and air (O2) as the oxidant. It tolerates a wide range of functionalized benzylic alcohol and aliphatic alcohols.