62969-97-5

Usage

Appearance

Pale yellow solid

Solubility

Insoluble in water

Chemical reactivity

Participates in Suzuki-Miyaura cross-coupling reactions, Sonogashira coupling reactions, and palladium-catalyzed carboxylation reactions

Applications

a. Synthesis of various organic molecules and pharmaceuticals
b. Precursor in the production of polymers and other organic compounds

Pharmacological activity

Studied for potential anti-inflammatory and anti-cancer properties

InChI:InChI=1/C16H14O/c17-16(13-15-9-5-2-6-10-15)12-11-14-7-3-1-4-8-14/h1-10,16-17H,13H2

Upstream product

• 1407998-86-0 2-(1,4-diphenylbut-3-yn-2-yl)isoindoline-1,3-dione 
• 122-78-1 phenylacetaldehyde 
• 536-74-3 phenylacetylene 
• 6738-06-3 phenylethynylmagnesium bromide 

Relevant academic research and scientific papers

Kinetic Resolution of Propargylic Ethers via [2,3]-Wittig Rearrangement to Synthesize Chiral α-Hydroxyallenes

An efficient kinetic resolution of propargyloxy dicarbonyl compounds via asymmetric [2,3]-Wittig rearrangement was achieved by using a chiral N,N′-dioxide/NiII complex catalyst. Various chiral α-allenyl alcohols were obtained in high enantioselectivities under mild conditions. The utility of this method was readily demonstrated in the asymmetric synthesis of the chiral 2,5-dihydrofuran derivative.

Cu(I)-catalyzed oxidative cyclization of enynamides: Regioselective access to cyclopentadiene frameworks and 2-aminofurans

An efficient Cu(I)-catalyzed oxidative cyclization of alkynyl-tethered enynamides for the construction of fused bicyclic cyclopentadiene derivatives is disclosed. The cascade proceeds through alkyne oxidation, carbene/alkyne metathesis, and formal (3 + 2)

Quinoxalinyl pyridopyrazine compound, preparation method and application thereof

The invention provides a quinoxalinyl pyridopyrazine compound and a preparation method thereof. According to the invention, the compound is directly synthesized from an alkyne ketone compound 3 synthesized from an alkyne compound and phenylacetaldehyde wi

Catalytic Ynone-Amidine Formal [4 + 2]-Cycloaddition for the Regioselective Synthesis of Tricyclic Azepines

A Ca(OTf)2- and self-promoted ynone-amidine atom-economic formal [4 + 2]-cycloaddition of various ynones with amidines is reported for the construction of highly functionalized tricyclic azepines. High reaction rate, ease of operation, and high product se

Asymmetric Propargylic Radical Cyanation Enabled by Dual Organophotoredox and Copper Catalysis

The first asymmetric propargylic radical cyanation was realized through a dual photoredox and copper catalysis. An organic photocatalyst serves to both generate propargyl radicals and oxidize Cu(I) species to Cu(II) species. A chiral Cu complex functions as an efficient organometallic catalyst to resemble the propargyl radical and cyanide in an enantio-controlled manner. Thus, a diverse range of optically active propargyl cyanides were produced with high reaction efficiency and enantioselectivities (28 examples, 57-97% yields and 83-98% ee). Moreover, mechanistic investigations including experiments and density functional theory calculations were performed to illustrate on the reaction pathway and stereochemical results.

Neighboring Carbonyl Group Assisted Hydration of Unsymmetrical Aryl Alkynes Overriding Regular Selectivity

A mild and highly regioselective gold-catalyzed hydration of γ-acetoxy aryl alkynes leading to anti-Markovnikov products by the assistance of a neighboring carbonyl group is presented. The reaction procedure operates under room temperature conditions with

Synthesis of Tetrasubstituted α,β-Unsaturated Aldehydes via Radical 1,4-Aryl Migration/Trifluoromethylthiolation Cascade Reaction of Aryl Propynyl Ethers

A one-pot synthesis of tetrasubstituted acrylaldehydes via difunctionalization of aryl propynyl ethers has been achieved, which involves a trifluoromethylthiolation process and a radical 1,4-aryl migration from oxygen to carbon. The reaction shows excellent conversion of aryl propynyl ethers into trifluoromethyl-containing α,β-unsaturated aldehydes through a radical pathway. (Figure presented.).

Enantioselective Alkynylation of Aromatic Aldehydes Catalyzed by a Sterically Highly Demanding Chiral-at-Rhodium Lewis Acid

The enantioselective catalytic alkynylation of aromatic aldehydes is reported using a sterically highly hindered bis-cyclometalated rhodium-based Lewis acid catalyst featuring the octahedral metal as the only stereogenic center. Yields of 58-98% with 79-9

Synthesis of Polysubstituted γ-Butenolides via a Radical Pathway: Cyclization of α-Bromo Aluminium Acetals and Comparison with the Cyclization of α-Bromoesters at High Temperature

Polysubstituted butenolides were obtained in good to high yields from α-bromoesters derived from propargyl alcohols by a one-pot reaction involving the radical cyclization of α-bromo aluminium acetals, followed by the oxidation of the resulting cyclic aluminium acetals in an Oppenauer-type process and migration of the exocyclic C-C bond into the α,β-position. Comparison with the direct cyclization of α-bromoesters at high temperature and under high dilution conditions is described. Deuterium-labelling experiments allowed us to uncover "invisible" 1,5-hydrogen atom transfers (1,5-HATs) that occur during these cyclization processes, together with the consequences of the latter in the epimerization of stereogenic centres. Compared to the classical approach, the cyclization of aluminium acetals proved to be highly chemoselective and its efficiency was illustrated by the short total syntheses of optically enriched γ-butenolides isolated from Plagiomnium undulatum and from Kyrtuhrix maculans.

Gold-catalyzed oxidative reactions of propargylic carbonates involving 1,2-carbonate migration: Stereoselective synthesis of functionalized alkenes

A gold-catalyzed oxidative reaction of propargylic carbonates or acetates using 3,5-dichloropyridine as the oxidant has been developed. The reaction provides efficient access to α-functionalized-α,β-unsaturated ketones with excellent regio- and diastereoc