37166-60-2

Upstream product

• 102-92-1 Cinnamoyl chloride 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 501072-27-1 (E)-3-hydroxy-1-phenyl-5-trimethylsilyl-1-penten-4-yne 
• 1066-54-2 trimethylsilylacetylene 
• 102-92-1 cinnamoyl chloride 
• 14371-10-9 (E)-3-phenylpropenal 
• 80783-99-9 N-methoxy-N-methylcinnamamide 
• 100-52-7 benzaldehyde 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 78965-33-0 3,4-dihydro-2-phenyl-2H-thiopyran-4-one 
• 37176-81-1 trans,trans-1,10-Diphenyldeca-1,9-dien-4,6-diin-3,8-dion 
• 37401-88-0 (E)-1-phenyl-1-penten-4-yn-3-one 

Relevant academic research and scientific papers

Preparation of unsymmetrical dialkenyl ketones from the reactions of alkenyl alkynyl ketones with Gilman reagents

Unsymmetrical dialkenyl ketones were prepared from the reactions of alkenyl alkynyl ketones with 0.55 equiv of lithium dialkylcuprates.

Asymmetric transfer hydrogenation of unsaturated ketones; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects

A detailed study has been completed on the asymmetric transfer hydrogenation (ATH) of a series of enones using Ru(II) catalysts. Electron-rich rings adjacent to the C[dbnd]O group reduce the level of C[dbnd]O reduction compared to C[dbnd]C. The ATH reaction can readily discriminate between double and triple bonds adjacent to ketones, reducing the double bond but leaving a triple bond intact in the major product.

Synthesis of 2-(hetero)aryl-5-(trimethylsilylethynyl)oxazoles from (hetero)arylacrylic acids

A three-step method for the synthesis of 2-(hetero)aryl-5-(trimethylsilylethynyl)oxazoles is described. Easily accessible bis(trimethylsilyl)acetylene and acrylic acid derivatives are used as starting materials for the preparation of mono- and disubstituted 5-(trimethylsilyl)pent-1-en-4-yn-3-ones. Oxidative phthalimidoaziridination of these enynones provides the key 2-acyl-1-phthalimidoaziridines that are further utilized in the thermal expansion of the three-membered ring to furnish the target functionalizable oxazoles.

Synthesis of 2,3-dihydrothiopyran-4-ones from 3-oxo-1-pentene-4-ynes

3-Oxo-1-pentene-4-ynes were converted with sodium sulfide or hydrogensulfide to give 2,6-disubstituted 2,3-dihydrothiopyran-4-one derivatives. The starting materials were prepared in two steps from terminal alkynes and α,β-unsaturated aldehydes.

Synthesis of unsymmetrically 2,6-disubstituted 2,3-dihydrothiopyran-4-ones

A series of 2,3-dihydrothiopyran-4-one derivatives with unequal substituents in the 2- and 6-position have been prepared by double conjugate addition of sulfide to enynones. These starting materials were accessed in two steps from terminal alkynes and α,β

Synthesis of unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes via alkylidene carbenoid rearrangements

Unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes are synthesized in four steps from commercially available aldehydes or carboxylic acids. The key step in this process involves a Fritsch-Buttenberg-Wiechell rearrangement, in which an alkylidene carbenoid intermediate subsequently rearranges to the desired polyyne. This rearrangement proceeds under mild conditions, and it is tolerant of a range of functionalities. In general, the procedurally facile formation of the dibromoolefinic precursors, in combination with the effectiveness of the rearrangement step, makes this procedure an attractive alternative to traditional methods for di- and triyne synthesis that utilize palladium or copper catalysis.

Friedel-crafts reactions of bis(trimethylsilyl)polyynes with acyl chlorides; a useful route to terminal-alkynyl ketones

Bis(trimethylsilyl)acetylenes, Me3Si(CC)nSiMe3, react with acyl chloride-aluminium chloride complexes, XC6H4 COCl·AlCl3 in methylene chloride at 0-20° to form the corresponding ketones XC6H4CO(CC)nSiMe3 in excellent (n = 1) or moderate (n = 2, 4) yield. Treatment of the products with aqueous methanolic borax results in virtually quantitative liberation of the terminal alkynyl ketones XC6H4CO(CC)nH. The method provides the first practical route to the ketotetraynes (n = 4) and usefully supplements existing oxidative methods for keto-monoyne and -diyne synthesis. The oxalyl chloride-aluminium chloride complex reacts with Me3SiCCSiMe3 to give the novel silyl-substituted heterocycle (I): {A figure is presented}.