1205-84-1

Usage

Uses

Used in Food and Beverage Industry:
Ethyl Trans-4-Phenyl-2-Butenoate is used as a flavoring agent for its fruity, sweet odor, enhancing the taste and aroma of various food and beverage products.
Used in Fragrance and Perfume Industry:
Ethyl Trans-4-Phenyl-2-Butenoate is used in the production of fragrances and perfumes, contributing to their pleasant and appealing scents.
Used in Medical Research:
Ethyl Trans-4-Phenyl-2-Butenoate is used as a potential biomarker for the diagnosis of kidney and bladder cancer, aiding in early detection and treatment of these conditions.

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 536-74-3 phenylacetylene 
• 96-09-3 styrene oxide 
• 1834-01-1 tributyl(methoxycarbonylmethylene)phosphonium bromide 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 122-78-1 phenylacetaldehyde 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 201230-82-2 carbon monoxide 
• 141-52-6 sodium ethanolate 
• 64-17-5 ethanol 
• 21040-45-9 Cinnamyl acetate 
• 5187-82-6 (ethoxycarbonylmethyl)dimethylsulfonium bromide 
• 4192-77-2 ethyl cinnamate 
• 74-95-3 1,1-dibromomethane 

Downstream Products

• 937-58-6 (3E)-4-phenyl-3-buten-1-ol 
• 875325-74-9 ethyl (2-phenylcyclopropyl)acetate 
• 1449251-99-3 C₁₂H₁₄O 
• 1449252-54-3 C₁₄H₁₈O₂ 
• 1454283-99-8 5-di-tert-butyl 2-diethyl 6,6'-(1,4-phenylene)bis(4-phenylpyridine-2,5-dicarboxylate) 
• 1454283-98-7 5-di-tert-butyl 2-diethyl 6,6'-(1,3-phenylene)bis(4-phenylpyridine-2,5-dicarboxylate) 
• 1454283-84-1 ethyl 4,5,6-triphenylpicolinate 
• 1454283-83-0 5-tert-butyl 2-ethyl 4-phenyl-6-styrylpyridine-2,5-dicarboxylate 
• 1454283-82-9 5-tert-butyl 2-ethyl 6-(furan-2-yl)-4-phenylpyridine-2,5-dicarboxylate 
• 1454283-81-8 5-tert-butyl 2-ethyl 4-phenyl-6-(thiophen-2-yl)pyridine-2,5-dicarboxylate 
• 1454283-80-7 5-tert-butyl 2-ethyl 6-(naphthalen-2-yl)-4-phenylpyridine-2,5-dicarboxylate 
• 1454283-79-4 5-tert-butyl 2-ethyl 6-(2-chlorophenyl)-4-phenylpyridine-2,5-dicarboxylate 
• 1454283-78-3 5-tert-butyl 2-ethyl 6-(4-nitrophenyl)-4-phenylpyridine-2,5-dicarboxylate 
• 1454283-77-2 2-ethyl 5-methyl 6-(4-methoxyphenyl)-4-phenylpyridine-2,5-dicarboxylate 

Relevant academic research and scientific papers

Thermal defect engineering of precious group metal-organic frameworks: Impact on the catalytic cyclopropanation reaction

We report on the engineering of defects in precious group metal (PGM)-based HKUST-1 (Hong Kong University of Science and Technology) analogues (RhII,II, RuII,II, RuII,III) and the ramification on the catalytic activity by using the cyclopropanation of styrene with ethyl diazoacetate (EDA) as an analytical probe to investigate complex metal-organic framework (MOF) structures. We have characterized the active sites within the extended frameworks by their activity, product distribution and stereoselectivity. The role of the metal, its oxidation state and the availability of open metal sites is elucidated. With a set of 17 samples including reference to Cu-HKUST-1, metal nanoparticles and existing literature, conclusions on the tuneability of paddlewheel complexes within self-supported porous and crystalline frameworks are presented. In particular, additional axial ligands (OAc-/Cl-) accounting for charge compensation at the mixed-valent RuII,III nodes seem responsible for side-product formation during catalysis. Thermal defect-engineering allows for controlled and preferential removal of those axial ligands accompanied by reduction of the average metal oxidation state. This enhances the number of open metal sites (OMS) and the catalytic activity as well as improving the chemoselectivity towards cyclopropanes. The preference towards formation of trans-cyclopropane is assigned to the steric crowding of the paddlewheel moiety. This diastereoselectivity gradually diminishes with rising defectiveness of the PGM-HKUST-1 analogues featuring modified paddlewheel nodes.

Palladium(0)-Catalyzed Alkoxycarbonylation of Allyl Phosphates and Acetates

Palladium-catalyzed alkoxycarbonylation of allyl phosphates under CO (1 atm) at 50 deg C proceeds highly efficiently to give the corresponding β,γ-unsaturated esters.The carbonylation of geranyl phosphate ((E)-11) under CO (1 atm) at 50 deg C gave ethyl ester of homogeranic acid ((E)-12) stereoselectively.The carbonylation takes place at least substituted allylic positions with inversion of configuration.Typically, the methoxycarbonylation of cis-5-(methoxycarbonyl)-2-cyclohexen-1-yl phosphate (cis-16) gave trans-dimethyl-2-cyclohexene-1,5-dicarboxylate (trans-17) selectively.Alkoxycarbonylation of allyl acetates is performed for the first time in the presence of a catalytic amount of bromide ion.The reaction can be rationalized by assuming the mechanism which involves oxidative addition of palladium(0) species to allyl acetates to give ?-allylpalladium acetate, fast ligand exchange of the acetate with bromide, insertion of carbon monoxide to give acylpalladium species, and alkoxylation.

Domino catalysis: Palladium-catalyzed carbonylation of allylic alcohols to β,γ-unsaturated esters

Make it green: The Pd-catalyzed carbonylation of allylic alcohols with aliphatic alcohols represents a cost-effective, salt-free, and atom-economic carbonylation process generating water as the sole by-product. Mechanistic studies uncovered a new domino C-O coupling/carbonylation reaction pathway. Copyright

SUBSTITUTION NUCLEOPHILE VINYLIQUE PAR LE REACTIF DE REFORMATSKY CATALYSSE PAR DES COMPLEXES DU NICKEL ET DU PALLADIUM ZEROVALENTS. SYNTHESE D'ESTERS β,γ-ETHYLENIQUES

Zerovalent complexes of palladium and nickel catalyse vinylic nucleophilic substitution by the Reformatsky reagent giving β,γ-ethylenic esters.Formation of a ?-vinylpalladium complex is the rate-determining step of the reaction.

Iridium complex-catalyzed carbonylation of allylic phosphates

[Ir(cod)Cl]2 with a ligand such as P(2-furyl)3, PPh2C6F5 or AsPh3 showed high catalytic activity for the carbonylation of allylic phosphates in the presence of alcohols to give the corresponding β,γ-unsaturated esters. The carbonylation of diethyl (E)-3-phenyl-2-propenyl phosphate in the presence of EtOH under an initial carbon monoxide pressure of 40 kg cm-2 at 100°C gave ethyl (E)-4-phenyl-3-butenoate in 90% yield. No (Z)-isomer was obtained. The reaction proceeded smoothly without using an amine as an additive. The carbonylation of 2-alkenyl diethyl phosphates in the presence of EtOH gave a mixture of ethyl (E)- and (Z)-3-alkenoate. The stereochemistry of the starting material was lost by syn-anti isomerization of the π-allyl iridium intermediate prior to the insertion of carbon monoxide into the iridium-carbon bond. Increasing the steric bulkiness of the substituent at the γ-position of the allyl system or increasing the initial carbon monoxide pressure increased the selectivity for a product with the same stereochemistry as the starting material.

Common precursor strategy for the synthesis of bestatin, amprenavir intermediate and syn-4-hydroxy-5-phenyl-γ-lactam

A common precursor strategy for the synthesis of bestatin hydrochloride, an anticancer agent, 1,3-diaminoalcohol, an amprenavir intermediate, and a syn-4-hydroxy-5-phenyl-γ-lactam intermediate of various bioactive molecules using an α,β-unsaturated ester as a common precursor is described. The protocol offers mild reaction conditions, good yields and excellent stereoselectivity.

PALLADIUM-CATALYZED DECARBOXYLATION-CARBONYLATION OF ALLYLIC CARBONATES TO GIVE β,Γ-UNSATURATED ESTERS UNDER MILD CONDITIONS

Allylic carbonates undergo facile palladium-catalyzed decarboxylation-carbonylation under mild conditions to give β,γ-unsaturated esters in high yields using palladium-phosphine complex as a catalyst.

Ligand-Controlled Palladium-Catalyzed Alkoxycarbonylation of Allenes: Regioselective Synthesis of α,β- and β,γ-Unsaturated Esters

The palladium-catalyzed regioselective alkoxycarbonylation of allenes with aliphatic alcohols allows to produce synthetically useful α,β- and β,γ-unsaturated esters in good yields. Efficient selectivity control is achieved in the presence of appropriate ligands. Using Xantphos as the ligand, β,γ-unsaturated esters are produced selectively in good yields. In contrast, the corresponding α,β-unsaturated esters are obtained with high regioselectivity in the presence of PPh2Py as the ligand. Preliminary mechanistic studies revealed that these two catalytic processes proceed by different reaction pathways. In addition, this novel protocol was successfully applied to convert an industrially available bulk chemical, 1,2-butadiene, into dimethyl adipate, which is a valuable feedstock for polymer and plasticizer syntheses, with high yield and TON (turnover number).

Visible Light Induced Br?nsted Acid Assisted Pd-Catalyzed Alkyl Heck Reaction of Diazo Compounds and N-Tosylhydrazones

A mild visible light-induced palladium-catalyzed alkyl Heck reaction of diazo compounds and N-tosylhydrazones is reported. A broad range of vinyl arenes and heteroarenes with high functional group tolerance, as well as a range of different diazo compounds, can efficiently undergo this transformation. This method features Br?nsted acid-assisted generation of hybrid palladium C(sp3)-centered radical intermediate, which allowed for new selective C?H functionalization protocol.

Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands

The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This limitation has now been overcome by the tailoring of ylide-functionalized phosphines to fit the requirements of Negishi couplings. Record-setting activities were achieved in palladium-catalyzed arylations of organozinc reagents with aryl electrophiles using a cyclohexyl-YPhos ligand bearing an ortho-tolyl-substituent in the backbone. This highly electron-rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively over triflate electrophiles, which permits consecutive coupling strategies.