54966-47-1

Upstream product

• 16205-84-8 ethyl 3-(trimethylsilyl)propynoate 
• 98-88-4 benzoyl chloride 
• 72036-37-4 ethyl 4-hydroxy-4-phenylbut-2-ynoate 
• 37174-94-0 ethyl 4-phenylbut-3-ynoate 
• 43165-51-1 sodium benzoylformate 
• 25726-04-9 phenylglyoxylyl chloride 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 623-47-2 propynoic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 152126-77-7 ethyl 3,4-dioxo-4-phenyl-2-triphenylphosphoranylidenebutanoate 

Downstream Products

• 1196458-79-3 ethyl (S)-4-phenyl-4-hydroxybut-2-ynoate 
• 73952-47-3 (R)-4-hydroxy-4-phenyl-but-2-ynoic acid ethyl ester 
• 166319-11-5 ethyl 4-benzoyl-2,5-dimethylpyrrole-3-carboxylate 
• 653605-66-4 ethyl (E)-4-oxo-4-phenyl-2-(pyrrolidin-1-yl)but-2-enoate 
• 653605-67-5 ethyl (E)-2-(morpholin-4-yl)-4-oxo-4-phenylbut-2-enoate 

Relevant academic research and scientific papers

Synthesis of trisubstituted allenamides utilizing 1,2-rearrangement of dialkoxyphosphoryl moiety under Br?nsted base catalysis

A new method for the synthesis of trisubstituted allenamides was developed by utilizing the 1,2-rearrangement of a dialkoxyphosphoryl moiety from carbon to nitrogen under Br?nsted base catalysis. The reaction would involve the catalytic generation of an α-amino propargyl anion through the key rearrangement, the addition to an electrophile at the α-position of the anionic intermediate, and the unprecedented rearrangement of a phosphoramidate moiety of the adduct, providing trisubstituted allenamides that are difficult to synthesize by using conventional methods.

Selenium-π-Acid Catalyzed Oxidative Functionalization of Alkynes: Facile Access to Ynones and Multisubstituted Oxazoles

Unprecedented selenium-catalyzed propargylic oxidation of alkynes is disclosed. Various propargylphosphonates and 3-alkynoates were efficiently converted to valuable ynones via unusual C-C triple bond migration and deselenenylation at a vinyl carbon. By the strategies of tautomerization of enamine intermediate and SN2 displacement, similar conditions were effective for the oxidative difunctionalization of ynamides to afford multisubstituted oxazoles with high regioselectivity. Mechanistic studies revealed these detailed processes.

Synthesis of N-methoxy-N-methyl-β-enaminoketoesters: New synthetic precursors for the regioselective synthesis of heterocyclic compounds

Weinreb amides react with the lithium or sodium acetylide of ethyl propynoate in a hitherto unexplored acyl substitution-conjugate addition sequence to furnish (E)-N-methoxy-N-methyl-β-enaminoketoesters. This approach provides a diverse entry to densely functionalized heterocyclic compounds, including pyrazoles through regioselective cyclocondensations with hydrazines in a microwave-assisted reaction.

Alkoxycarbonyl-Substituted 3-Trifloxypropene Iminium Salts and Iminium-Substituted Δ2,3-Butenolides: Synthesis and Reactivity toward Nucleophiles

Triflic anhydride reacts regioselectively with the ethoxy-carbonyl- substituted enaminones 6a-h to give the novel 3-trifloxypropene iminium salts 7a-d or iminium-substituted Δ2,3-butenolides 8a-d and 9a-d in good yields. Hydride reduction of the iminium salts 7a,b affords new 2-dialkylamino-4-trifloxy-but-3-enoates 13a,b, while mild hydrolysis generates 2-oxo-4-trifloxy-butenoates 14a,b. Butenolides 8b,d, and 9c react with methyl hydrazine to afford 4-dialkylamino-pyridazin-3(2H)-ones 12a-c.

Oxalylmethylenephosphoranes: III. Synthesis and Flash Vacuum Pyrolysis of Ethyl 4-Aryl-3-triphenylphosphoranylidene-2,4-dioxobutanoates

Ethyl 4-aryl-3-triphenylphosphoranylidene-2,4-dioxobutanoates were obtained by C-acylation of (aroylmethylene)(triphenyl)phosphorane with ethyl oxalyl chloride. Under conditions of vacuum flash pyrolysis at 500°C the former eliminate triphenylphosphine oxide to give ethyl 4-aryl-4-oxo-2-butynoates.

Direct alkynyl group transfer from silicon to copper: New preparation method of alkynylcopper (I) reagents

A first observation of the direct alkynyl group transfer from silicon to copper is reported. The silicon group of alkynylsilanes was smoothly replaced by copper (I) chloride in DMI to give the corresponding copper (I) acetylides. This transformation was a

Flash Vacuum Pyrolysis of Stabilized Phosphorous Ylides. Part 5. Selective Extrusion of Ph3PO from β,γ,β'-Trioxo Ylides to give Doacylalkynes

Sixteen examples of the previously unknown trioxo ylides 7 have been prepared by acylation of stabilized phosphorus ylides 8 with α-oxo acid chlorides 9.Extrusion of Ph3PO from these is readily achieved using FVP at 500 deg C in most cases, to afford the diacylalkynes 10 in moderate yield.Three examples failed to give the expected alkynes and the nature of the processes involved in these cases is certain.Fully assigned 13C NMR spectra are presented for the ylides and an unexpected pattern is observed in the value of JP-C for the three carbonyl carbons depending on the nature of the substituents present.There is some correlation between the value of 2JP-C for the central carbonyl carbon and the success of the pyrolysis although this is not complete.The method has been used to prepare a specifically 13C labelled acetylenic diester 14.

Pyrolysis of β,γ,β'-trioxo phosphorus ylides: Convenient synthesis of symmetrical and unsymmetrical diacylalkynes

Flash vacuum pyrolysis of a series of 1,2,4-trioxo-3-triphenylphosphoranylidene-butane derivatives, formed by acylation of β-oxo-phosphorus ylides with α-oxo-acid chlorides, results in extrusion of Ph3PO exclusively across the 2,3-position to give diacylalkynes.