308357-39-3

Upstream product

• 4341-76-8 Ethyl 2-butynoate 
• 536-74-3 phenylacetylene 
• 122135-89-1 ethyl (Z)-3-methyl-5-phenylpent-2-en-4-ynoate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 1817-57-8 4-phenyl-3-butyne-2-one 

Downstream Products

• 127915-54-2 ethyl 5-phenylhexa-3,4-dienoate 
• 122135-89-1 ethyl (Z)-3-methyl-5-phenylpent-2-en-4-ynoate 
• 4467-30-5 4-methyl-6-phenyl-2H-pyran-2-one 
• 50405-77-1 6-phenyl-4-methyl-1-hydroxypyridin-2(1H)-one 
• 149929-75-9 trans-3-methyl-5-phenyl-2-penten-4-yn-1-ol 

Relevant academic research and scientific papers

Chemoselective Biohydrogenation of Alkenes in the Presence of Alkynes for the Homologation of 2-Alkynals/3-Alkyn-2-ones into 4-Alkynals/Alkynols

The chemoselective hydrogenation of alkenes in the presence of alkynes is a very challenging transformation to achieve with traditional chemical methods. The development of an effective procedure to perform this transformation would enrich the tool-kit available to organic chemists for the development of useful synthetic routes, and the creation of novel structural motifs. The reduction of activated alkene bonds by ene-reductases (ERs) is completely chemoselective, because of the mechanism of the reaction. Thus, we investigated the use of ERs belonging to the Old Yellow Enzyme family for the reduction of α,β-unsaturated aldehydes with a conjugated C≡C triple bond at the γ position. This reaction was exploited as the key step for the development of an effective homologation route to convert aryl and alkyl substituted propynals and butynones into 4-alkynals and 4-alkynols, avoiding some troublesome or hazardous steps of known synthetic routes. (Figure presented.).

Discovery of a novel series of N-hydroxypyridone derivatives protecting astrocytes against hydrogen peroxide-induced toxicity via improved mitochondrial functionality

Astrocytes play a key role in brain homeostasis, protecting neurons against neurotoxic stimuli such as oxidative stress. Therefore, the neuroprotective therapeutics that enhance astrocytic functionality has been regarded as a promising strategy to reduce brain damage. We previously reported that ciclopirox, a well-known antifungal N-hydroxypyridone compound, protects astrocytes from oxidative stress by enhancing mitochondrial function. Using the N-hydroxypyridone scaffold, we have synthesized a series of cytoprotective derivatives. Mitochondrial activity assay showed that N-hydroxypyridone derivatives with biphenyl group have comparable to better protective effects than ciclopirox in astrocytes exposed to H2O2. N-hydroxypyridone derivatives, especially 11g, inhibited H2O2-induced deterioration of mitochondrial membrane potential and oxygen consumption rate, and significantly improved cell viability of astrocytes. The results indicate that the N-hydroxypyridone motif can provide a novel cytoprotective scaffold for astrocytes via enhancing mitochondrial functionality.

Ruthenium/halide catalytic system for C-C bond forming reaction between alkynes and unsaturated carbonyl compounds

A ruthenium complex [triruthenium dodecacarbonyl, Ru3(CO) 12] in the presence of bis(triphenylphosphine)iminium chloride ([PPN]Cl) catalyzes the conjugate addition of terminal alkynes to alkyl acrylates to give high yields of γ,δ-alkynyl esters. On the other hand, the linear codimerization reaction of terminal alkynes with alkyl acrylates proceeds in the presence of a catalytic amount of Ru 3(CO)12 and lithium iodide to give the corresponding conjugate dienes. These two different types of catalytic carbon-carbon bond forming reactions are controlled only by the nature of halide ions, either a chloride or an iodide, with other conditions being kept almost the same.

Palladium-catalyzed highly chemo- and regioselective formal [2 + 2 + 2] sequential cycloaddition of alkynes: A renaissance of the well known trimerization reaction?

A new concept of highly chemo- and regioselective formation of the benzene ring by a palladium-catalyzed formal [2 + 2 + 2] sequential intermolecular trimerization of, alkynes is proposed. Homodimerization of terminal alkynes and subsequent [4 + 2] benzannulation with diynes gives tetrasubstituted benzenes in moderate to good yields. The introduction of two different alkynes (terminal and internal) in the first step of the sequence allows for construction of pentasubstituted benzenes from three different acyclic acetylenic units. In all cases the tetra- and pentasubstituted benzenes are formed as a single reaction product without being accompanied by any of regio- or chemoisomers. A significant acceleration of the sequential trimerization reaction in the presence of Lewis acid/phosphine combined system was observed. Mechanistic studies reveal that the Lewis acid assisted isomerization of the E-enyne formed in the first step of the sequence to the more reactive Z-isomer is responsible for the observed acceleration effect. The proposed methodology provides a conceptually new and synthetically useful route to multifunctional aromatic compounds.

New efficient catalysts for the palladium-catalyzed coupling of alkynes to enynes

Palladium complexes with phosphinooxazoline ligands are very efficient catalysts for the coupling of alkynes to enynes. The catalyst system could be employed in solvent-free reactions and provided an efficient means for the regiocontrol of cross-coupling