4891-38-7

Usage

Uses

Used in Chemical Synthesis:
METHYL PHENYLPROPIOLATE is used as a key intermediate for the synthesis of various organic compounds, such as bicyclohexadienes, cis-methyl cinnamate, and (E)-alkyl 3-(dialkoxyphosphoryl)-3-phenylacrylate derivatives. Its reactivity and versatility make it a valuable component in the development of new chemical products.
Used in Organoiron Carbonyl Complexes:
METHYL PHENYLPROPIOLATE is used as a reactant in the formation of organoiron carbonyl complexes when combined with Fe2(CO)9. These complexes have potential applications in various fields, including catalysis and materials science.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 4859, 1987 DOI: 10.1021/jo00231a007Tetrahedron Letters, 21, p. 849, 1980 DOI: 10.1016/S0040-4039(00)71522-X

InChI:InChI=1/C10H8O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-6H,1H3

Upstream product

• 67-56-1 methanol 
• 637-44-5 phenylpropyolic acid 
• 56950-09-5 phenyl(phenylethynyl)tellane 
• 201230-82-2 carbon monoxide 
• 932-88-7 1-iodo-2-phenylethyne 
• 79069-32-2 phenyl(phenylethynyl)iodonium tosylate 
• 21770-48-9 methyl 2,3-dibromo-3-phenylpropanoate 
• 27412-71-1 5-phenyl-1H-pyrazol-3(2H)-one 
• 21473-06-3 1-phenylpropynoyl-1H-imidazole 
• 536-74-3 phenylacetylene 
• 24127-62-6 methyl 2-bromo-3-phenylacrylate 
• 108-95-2 phenol 
• 79-22-1 methyl chloroformate 
• 108932-57-6 trimethyl phenylorthopropiolate 

Downstream Products

• 5932-28-5 4-phenyl-1H-pyrazole-3-carboxylic acid methyl ester 
• 21031-22-1 methyl 3-phenyl-1H-pyrazole-4-carboxylate 
• 50561-87-0 4,5-diphenyl-1⁽²⁾H-pyrazole-3-carboxylic acid methyl ester 
• 24161-43-1 methyl 3-phenylbicyclo<2.2.1>hepta-2,5-diene-2-carboxylate 
• 38750-49-1 3-methoxy-3-phenypropenoate 
• 116429-08-4 methyl 3-phenyl-3,3-dimethoxypropionate 
• 75024-36-1 2,3-dicyano-3-phenyl-propionic acid methyl ester 
• 2555-31-9 7-methoxy-4-phenyl-2H-chromen-2-one 
• 854692-89-0 1,1-bis-biphenyl-4-yl-3-phenyl-prop-2-yn-1-ol 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 708-82-7 α,β-dibromo-cis-cinnamic acid 
• 708-81-6 (E)-2,3-Dibromo-3-phenyl-acrylic acid 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 90800-02-5 2-chloro-1-methoxycarbonyl-2-phenyl-vinylmercury ⁽¹⁺⁾; chloride 

Relevant academic research and scientific papers

SF5-Enolates in Ti(IV)-Mediated Aldol Reactions

The F···Ti bonding in the transition structures determines high trans- and syn-diastereoselectivities for aldol reactions of SF5-acetates with aldehydes in the presence of TiCl4 in the non-nucleophilic solvent CH2Cl2

A new method for synthesis of methyl arylpropiolates by direct heck coupling of aryl iodide and methyl propiolate in presence of K2CO3

A protocol for the efficient direct cross coupling of esters of propiolic acid and of aryl iodides with a Pd(PPh3)2Cl2/copper(I) iodide catalyst system in the presence of K2CO3 has been developed.

Co3O4 nanoparticles embedded in triple-shelled graphitic carbon nitride (Co3O4/TSCN): a new sustainable and high-performance hierarchical catalyst for the Pd/Cu-free Sonogashira–Hagihara cross-coupling reaction

Inspired by the synthesis of triple-shelled periodic mesoporous organosilica hollow spheres, a straightforward and controllable approach for the preparation of Co3O4 NPs embedded in triple-shelled graphitic carbon nitride has been es

Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water

Phosphine-mediated reductions of substituted propynoic esters and amides in the presence of water yield the partially reduced α,β-unsaturated esters and amides with highZ-selectivity. The competitivein situ ZtoE-isomerization of the product in some cases lowers theZtoEratios of the isolated α,β-unsaturated carbonyl products. Reaction time and the amounts of phosphine and water in the reaction mixture are the key experimental factors which control the selectivity by preventing or reducing the rates ofZ- toE-product isomerization. Close reaction monitoring enables isolation of theZ-alkenes with high selectivities. The computational results suggest that the reactions could be highlyZ-selective owing to the stereoselective formation of theE-P-hydroxyphosphorane intermediate.

trans-Selective hydrocyanation of ynoates, ynones and ynoic acids catalyzed by nucleophilic phosphines

trans-Selective hydrocyanation of ynoates and ynones in the presence of TMSCN and an alcohol additive are catalyzed by nucleophilic phosphines. The trisubstituted E-olefin products of anti-addition of hydrogen cyanide to the alkyne are produced with high regio- and stereoselectivity. The alcohol additive reacts with TMSCN to produce hydrogen cyanide in situ. Ynoic acids undergo the phosphine catalyzed hydrocyanation in the presence of TMSCN under aprotic conditions only. In these reactions, TMSCN reacts with the acid to generate hydrogen cyanide and the silyl ester which, unlike the acid, undergoes phosphine catalyzed hydrocyanation and gives the stereo-defined E-2-cyano-acrylic acids after work up.

Esterification or Thioesterification of Carboxylic Acids with Alcohols or Thiols Using Amphipathic Monolith-SO3H Resin

We have developed a method for the esterification of carboxylic acids with alcohols using amphipathic, monolithic-resin bearing sulfonic acid moieties as cation exchange functions (monolith-SO3H). Monolith-SO3H efficiently catalyzed the esterification of aromatic and aliphatic carboxylic acids with various primary and secondary alcohols (1.55.0 equiv) in toluene at 6080 °C without the need to remove water generated during the reaction. The amphipathic property of monolith-SO3H facilitates dehydration due to its capacity for water absorption. This reaction was also applicable to thioesterification, wherein the corresponding thioesters were obtained in excellent yield using only 2.0 equiv of thiol in toluene, although heating at 120 °C was required. Moreover, monolith-SO3H was separable from the reaction mixtures by simple filtration and reused for at least five runs without decreasing the catalytic activity.

Synthesis method of aryl-substituted alkyne

The invention relates to the technical field of synthesis of aryl substituted alkyne, and discloses a synthetic method of an aryl-substituted alkyne, and discloses a synthesis method of an aryl-substituted alkyne. Aryl boronic acid and divalent copper compounds, 8 - hydroxyquinoline, an oxidizing agent and an inorganic base are added to the reaction solvent, and the aryl substituted alkyne is obtained by stirring and separating after stirring at room temperature. Compared with the existing sonogashira reaction, the synthesis method disclosed by the invention realizes the aryl reaction of the lean electron alkyne through the oxidative coupling reaction, avoids Sonogashira reaction required precious palladium catalyst, can react at room temperature, and is mild in reaction condition and high in product yield.

Organocatalytic trans Phosphinoboration of Internal Alkynes

We report the first trans phosphinoboration of internal alkynes. With an organophosphine catalyst, alkynoate esters and the phosphinoboronate Ph2P-Bpin are efficiently converted into the corresponding trans-α-phosphino-β-boryl acrylate products in moderate to good yield with high regio- and Z-selectivity. This reaction operates under mild conditions and demonstrates good atom economy, requiring only a modest excess of the phosphinoboronate. X-ray crystallography experiments allowed structural assignment of the unprecedented and densely functionalized (Z)-α-phosphino-β-boryl acrylate products.

Enantioselective Fluorination of α-Branched β-Ynone Esters Using a Cinchona-Based Phase-Transfer Catalyst

Herein, we report the fluorination of α-branched β-ynone esters to afford their corresponding quaternary fluorinated products with good enantioselectivity (ee = 73-90%) using a cinchona-based phase-transfer catalyst. α-Branched β-ynone esters possess a highly acidic α-proton and form their corresponding enolate as a single isomer, which allows the enantioselective fluorination reaction to occur under standard cinchona-based phase-transfer catalyst conditions. Moreover, the obtained α-fluorinated product can be treated with [(SPhos)AuNTf2] (1 mol %) to afford a fluorinated 3,5-diketo carboxylic acid.

Ynamide-Mediated Intermolecular Esterification

An ynamide-mediated one-pot, two-step intermolecular esterification via the condensation of carboxylic acids with nucleophilic hydroxyl species was reported. A broad substrate scope with respect to carboxylic acids, alcohols, and phenols was observed. The α-acyloxyenamide intermediates formed by the addition of carboxylic acids to ynamides proved to be effective acylating reagents for the esterification of alcohol and phenol derivatives with the assistance of base catalysis. Notably, the racemization of the α-chiral center of carboxylic acids can be avoided.