16619-68-4

Upstream product

• 109365-86-8 1-(o-hydroxyphenyl)-3-phenylpropargylic alcohol 
• 90-02-8 salicylaldehyde 
• 536-74-3 phenylacetylene 
• 4440-01-1 lithium phenylacetylide 
• 1441-87-8 salicyloyl chloride 
• 6738-06-3 phenylethynylmagnesium bromide 
• 525-82-6 FLAVONE 
• 119-36-8 methyl salicylate 

Downstream Products

• 525-82-6 FLAVONE 
• 104959-21-9 Potassium; 2-((Z)-3-phenyl-3-p-tolylsulfanyl-acryloyl)-phenolate 
• 104959-20-8 Potassium; 2-((E)-3-phenyl-3-p-tolylsulfanyl-acryloyl)-phenolate 
• 36685-41-3 (Z)-4'-methoxyaurone 
• 582-04-7 aurone 
• 37542-14-6 aurone 
• 109619-12-7 (Z)-1-(2-Hydroxy-phenyl)-3-isopropylamino-3-phenyl-propenone 
• 109619-15-0 2-(β-Anilino-cinnamoyl)-phenol 
• 109619-16-1 (Z)-3-Allylamino-1-(2-hydroxy-phenyl)-3-phenyl-propenone 
• 35614-55-2 3-benzylamino-1-(2-hydroxyphenyl)-3-phenyl-2-propenone 
• 1607814-81-2 N,N-diphenyl 2-(3-phenylprop-2-ynoyl)phenyl carbamate 
• 16619-67-3 1-(2-acetoxy-phenyl)-3-phenyl-2-propyn-1-one 
• 1415385-07-7 3-[(naphthalen-2-yl)carbonyl]-2-phenyl-4H-chromen-4-one 
• 1415385-01-1 2-(3-phenylprop-2-ynoyl)phenyl naphthalene-2-carboxylate 

Relevant academic research and scientific papers

Ligand-promoted, copper nanoparticles catalyzed oxidation of propargylic alcohols with TBHP or Air as Oxidant

A highly efficient oxidation of propargylic alcohols to ynones was catalyzed by copper nanoparticles (Cu Nps) with TBHP as an oxidant at room temperature. With bipyridine as the ligand, the reaction was accelerated significantly and led in good to excellent yields to a variety of propargylic alcohols. Furthermore, with Cu Nps as the catalyst, molecular oxygen in air could be utilized as oxidant effectively in the presence of bpy ligand. Georg Thieme Verlag Stuttgart - New York.

Palladium-catalyzed synthesis of aurone from salicyloyl chloride and phenylacetylene

Salicyloyl chloride has been found to react with phenylacetylene under the catalytic action of a palladium(O) complex with trioctylamine as ligand to give o-hydroxyphenyl phenylalkynyl ketone as the main product.The ketone undergoes selective cyclization to aurone in the presence of a palladium(O)-triphenylphosphine catalyst.

Bioactivity-Guided Synthesis Accelerates the Discovery of 3-(Iso)quinolinyl-4-chromenones as Potent Fungicide Candidates

Fungal infections could cause tremendous decreases in crop yield and quality. Natural products, including flavonoids and (iso)quinolines, have always been an important source for lead discovery in medicinal and agricultural chemistry. To promote the discovery and development of new fungicides, a series of 3-(iso)quinolinyl-4-chromenone derivatives was designed and synthesized by the active substructure splicing principle and evaluated for their antifungal activities. The lead optimization was guided by bioactivity. The bioassay data revealed that the 3-quinolinyl-4-chromenone 13 showed significant in vitro activities against S. sclerotiorum, V. mali, and B. cinerea with EC50 values of 3.65, 2.61, and 2.32 mg/L, respectively. The 3-isoquinolinyl-4-chromenone 25 exhibited excellent in vitro activity against S. sclerotiorum with an EC50 value of 1.94 mg/L, close to that of commercial fungicide chlorothalonil (EC50 = 1.57 mg/L) but lower than that of boscalid (EC50 = 0.67 mg/L). For V. mali and B. cinerea, 3-isoquinolinyl-4-chromenone 25 (EC50 = 1.56, 1.54 mg/L) showed significantly higher activities than chlorothalonil (EC50 = 11.24, 2.92 mg/L). In addition, in vivo experiments proved that compounds 13 and 25 have excellent protective fungicidal activities with inhibitory rates of 88.24 and 94.12%, respectively, against B. cinerea at 50 mg/L, while the positive controls chlorothalonil and boscalid showed inhibitory rates of 76.47 and 97.06%, respectively. Physiological and biochemical studies showed that the primary action of mechanism of compounds 13 and 25 on S. sclerotiorum and B. cinerea may involve changing mycelial morphology and increasing cell membrane permeability. In addition, compound 13 may also affect the respiratory metabolism of B. cinerea. This study revealed that compounds 13 and 25 could be promising candidates for the development of novel fungicides in crop protection.

METHOD FOR SYNTHESIZING (Z)-AURONE AND DERIVATIVE COMPOUNDS THEREOF

One embodiment of the present invention is described below. Provided is (Z)-operon comprising o - (alkanone -1 - yl) phenol or its derivative compound in a thallium (Tl) catalyst and an cyclization step for cyclizing the compound under an organic solvent, and a method for producing the derivative compound.

Copper-catalyzed method for preparing aldehyde or ketone compound by oxidizing alcohol with oxygen as oxidizing agent and application

The invention discloses a copper-catalyzed method for preparing an aldehyde or ketone compound by oxidizing alcohol with oxygen as an oxidizing agent. Reaction is performed in an organic solvent for 4-48 hours at room temperature by using copper salt and nitroxide free radicals as catalysts and oxygen or air as an oxidizing agent to efficiently oxidize an alcohol compound into the corresponding aldehyde or ketone compound. The method is simple to operate, free of chlorides corrosive to equipment, available in raw materials and reagents, mild in reaction conditions, wide in substrate universality, good in functional group compatibility, convenient in separation and purification, environmentally friendly in the whole process and free of pollution, and is a method suitable for industrial production.

One-pot Synthesis of Aurones through Oxidation-cyclization Tandem Reaction Catalyzed by Copper Nanoparticles Catalyst

Aurones were synthesized through an oxidation-cyclization tandem reaction of 2-(1- hydroxyprop-2-ynyl)phenols catalyzed by copper nanoparticles (Cu NPs) with bipyridine as the ligand. In the reaction, oxygen worked as a green and mild oxidant to give the best results. Cu NPs were dually activated by bipyridine ligand and water, and showed highly efficient catalytic activities to the oxygen oxidation and the cylization to give aurones and flavonoids.

One Pot Synthesis of γ-Benzopyranones via Iron-Catalyzed Aerobic Oxidation and Subsequent 4-Dimethylaminopyridine Catalyzed 6-endo Cyclization

One-pot synthesis of γ-benzopyranones was realized in decent yields and excellent regioselectivities via iron-catalyzed aerobic oxidation and 4-dimethylaminopyridine-catalyzed cyclization of related propargylic alcohols. Derivatizations to aromatic substituted γ-benzopyranones and synthesis of naturally occurring 3′,4′-dimethoxyflavone have also been realized. (Figure presented.).

Divergence in Ynone Reactivity: Atypical Cyclization by 3,4-Difunctionalization versus Rare Bis(cyclization)

Functionalized ynones can be activated by Tf2C=CH2, which was generated in situ, to form zwitterionic species. These species were trapped in an intramolecular fashion by several nucleophiles to generate two major types of triflones in a divergent manner. Through fine-tuning of the reaction temperature, bis(triflyl)-6-membered- or (triflyl)-5-membered-fused-heterocycles were achieved in reasonable yields in a totally selective manner. In this way, bis(triflyl)flavones, bis(triflyl)thioflavones, bis(triflyl)selenoflavones, (triflyl)benzothienopyrans, (triflyl)benzoselenophenopyrans, (triflyl)vinyl aurones, and (triflyl)pyranoindoles were constructed. Conceivable mechanistic pathways were suggested on the basis of the isolation of several intermediates and the results from control experiments.

Dual-immobilized copper catalyst: Carbon nitride-supported copper nanoparticles catalyzed oxidation of propargylic alcohols

Copper nanoparticles were supported and modified by carbon nitride, which was utilized as support and might work as a kind of immobilized N-donor ligand. The modified nanoparticle catalyst was evaluated with the oxidation of propargylic alcohols and showed highly catalytic efficiency as well as significant ligand or support effect in the reaction. The dual-immobilized nanoparticle catalyst could be recycled for 3 times at least without an obvious decrease in catalytic activities.