29577-34-2

Usage

Properties

Chemical compound

Specific content

Also known as allyl phenyl propiolate
Used in consumer products such as perfumes, soaps, and cosmetics
Used in manufacturing pharmaceuticals
Used as synthetic intermediate in organic chemistry
Should be handled and stored with caution

Upstream product

• 107-18-6 allyl alcohol 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 124-38-9 carbon dioxide 
• 536-74-3 phenylacetylene 
• 107-05-1 3-chloroprop-1-ene 
• 106-95-6 allyl bromide 
• 637-44-5 phenylpropyolic acid 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 107-11-9 1-amino-2-propene 

Downstream Products

• 143121-35-1 6-Phenyl-3a,4-dihydro-3H-cyclopenta[c]furan-1,5-dione 
• 592-51-8 4-Pentenenitrile 
• 4289-20-7 1-phenyl-4-penten-1-yne 
• 1019264-81-3 (Z)-α-(1'-chlorobenzylidene)-β-methyl-γ-butyrolactone 
• 1130965-30-8 (1R,5S)-1-benzoyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 1266335-10-7 C₁₂H₁₁FO₂ 
• 1342795-47-4 C₁₂H₁₂O₂ 
• 122057-55-0 (E)-2-Methyl-penta-2,4-dienoic acid methyl ester 
• 899797-21-8 (Z)-methyl 2-phenylpenta-2,4-dienoate 

Relevant academic research and scientific papers

Selective Alkynylallylation of the C?C σ Bond of Cyclopropenes

A Pd-catalyzed regio- and stereoselective alkynylallylation of a specific C?C σ bond in cyclopropenes, using allyl propiolates as both allylation and alkynylation reagents, has been achieved for the first time. By merging selective C(sp2)-C(sp3) bond scission with conjunctive cross-couplings, this decarboxylative reorganization reaction features fascinating atom and step economy and provides an efficient approach to highly functionalized dienynes from readily available substrates. Without further optimization, gram-scale products can be easily obtained by such a simple, neutral, and low-cost catalytic system with high TONs. DFT calculations afford a rationale toward the formation of the products and indicate that the selective insertion of the double bond of cyclopropenes into the C-Pd bond of ambidentate Pd complex and the subsequent nonclassical β-C elimination promoted by 1,4-palladium migration are critical for the success of the reaction.

Synthesis of aryl allyl alkynes via reaction with allyl amine and aryl alkynoic acids through decarboxylation

Allyl alkynoic esters were synthesized by the reaction of allyl amines and alkynoic acids via deaminative esterification. The reaction of allyl alkynoic esters with Pd(dba)2 and Xantphos in digylme at 110 °C for 12 h afforded the desired decarb

Unprecedented Multicomponent Organocatalytic Synthesis of Propargylic Esters via CO2 Activation

An efficient and straightforward organocatalytic method for the direct, multicomponent carboxylation of terminal alkynes with CO2 and organochlorides, towards propargylic esters, is reported for the first time. 1,3-Di-tert-butyl-1H-imidazol-3-ium chloride, a simple, widely-available, stable, and cost-efficient N-heterocyclic carbene (NHC) precursor salt was used as the (pre)catalyst. A wide range of phenylacetylenes, bearing electron-withdrawing or electron-donating substituents, react with allyl-chlorides, benzyl chlorides, or 2-chloroacetates, providing the corresponding propargylic esters in low to excellent yields. DFT calculations on the mechanism of this transformation indicate that the reaction is initiated with the formation of an NHC-carboxylate, by addition of the carbene to a molecule of CO2. Then, the nucleophilic addition of this species to the corresponding chlorides has been computed to be the rate limiting step of the process.

3 - Aryl methylacetylene acid and 3 - aryl methylacetylene ester preparation method of compound (by machine translation)

The invention relates to a 3 - aryl methylacetylene acid compound preparation method: formula (I) shown phenylacetylene compound with carbon dioxide under the action of alkali, in solvent dimethyl sulfoxide in 40 - 70 °C under reaction, as shown in formula (II) of the 3 - aryl methylacetylene acid compounds, more than normal pressure of the body reaction in water-free, oxygen-free inert atmosphere, the reaction route is as follows: Wherein R1 Selected from hydrogen, alkyl, alkoxy, phenyl, nitro or halogen. The invention further provides a 3 - aryl methylacetylene ester preparation method of compound: adopting the above-mentioned method of the formula (II) is shown in the 3 - aryl methylacetylene acid compound, then adding the halogenated hydrocarbon or tosylates, after the in-situ reaction of the formula (III) is shown in the 3 - aryl methylacetylene ester compound: Wherein R2 Is selected from alkyl, benzyl or allyl. The method of the invention does not need to transition metal or rare earth metal catalyst, normal pressure reaction, mild condition, pervasive good substrate. (by machine translation)

Effective Synthesis of Benzyl 3-Phenylpropiolates Via Copper(I)-Catalyzed Esterification of Alkynoic Acids with Benzyl Halides under Ligand-Free Conditions

We developed an efficient way to prepare benzyl 3-phenylpropiolates via copper-catalyzed coupling between corresponding benzyl halides and alkynoic acids under ligand-free condition. This methodology is also suitable for aromatic and α,β-unsaturated acids. The desired esters could be obtained in good yields.

Copper(II)-Catalyzed β-Borylation of Acetylenic Esters in Water

A method for the β-borylation of alkynoates has been developed. In the presence of bis(pinacolato)diboron and catalytic amounts of both copper(II) and 4-picoline, substituted alkynoates undergo borylation in a regio-, stereo-, and chemoselective fashion. The reaction is performed under mild conditions using water as solvent and open to the atmosphere to exclusively afford (Z)-β-boryl-α,β-unsaturated esters.

Synthesis of 1,4-dienes by Pd(II)-catalyzed haloallylation of alkynes with allylic alcohols in ionic liquids

A Pd-catalyzed haloallylation of alkynes with allyl alcohols in ionic liquids has been reported. Both chloroallylation and bromoallylation can be easily carried out with high selectivity. A variety of 1,4-dienes were formed in moderate to excellent yields. The reaction system of the Pd catalyst as well as the ionic liquid can be recycled for several times. And the ionic liquid acts as not only a solvent in the reaction, but also provides the excess halide ions to control Z/E selectivity and acts as a ligand inhibit the β-hydride elimination.

Carboxylation of alkynylsilanes with carbon dioxide mediated by cesium fluoride in DMSO

The facile syntheses of a variety functionalized propiolic acids were achieved by carboxylation of alkynylsilanes with carbon dioxide mediated by cesium fluoride under ambient conditions. This journal is The Royal Society of Chemistry 2013.

CuII-exchanged montmorillonite K10 clay-catalyzed direct carboxylation of terminal alkynes with carbon dioxide

A new, simple and straight-forward protocol for direct carboxylation of terminal alkynes has been developed using CuII-montmorillonite K10 clay as a heterogeneous catalyst and CO2 as the C1 carbon feedstock. Also coupling of terminal alkynes with CO2 (1 atm) in the presence of alkyl halides has been achieved under the same reaction conditions, thereby providing access to a variety of functionalized alkyl-2-alkynoates in high yields.

Ligand-free Ag(I)-catalyzed carboxylative coupling of terminal alkynes, chloride compounds, and CO2

Simple silver(I) slats were found to be highly efficient and selective catalyst for carboxylative coupling of aryl- or alkyl-substituted terminal alkynes, CO2, and various allylic, propargylic or benzylic chlorides to exclusively yield function