100883-23-6

Upstream product

• 1415425-82-9 (E)-3-chloro-1-phenyloct-2-en-1-one 
• 98-88-4 benzoyl chloride 
• 27259-10-5 1-phenyloct-2-yn-1-one 
• 552-89-6 2-nitro-benzaldehyde 
• 18495-26-6 1-bromo-2-heptyne 
• 100-52-7 benzaldehyde 
• 35281-66-4 (±)-1-phenyloct-3-yn-1-ol 
• 628-71-7 1-Heptyne 

Downstream Products

• 80866-26-8 2-n-butyl-5-phenylfuran 
• 96412-99-6 1-phenyl-(2E,4E)-octa-2,4-dien-1-one 

Relevant academic research and scientific papers

1,3-Dienones and 2H-Pyran-2-ones from Soft α-Vinyl Enolization of β-Chlorovinyl Ketones: Defined Roles of Br?nsted and Lewis Base

The eliminative reaction pathways of (E)-β-chlorovinyl ketones were investigated in the presence of both Br?nsted and Lewis bases. The Br?nsted base, Et3N, effected the soft α-vinyl enolization of (E)-β-chlorovinyl ketones to [3]cumulenol intermediates; in turn, a catalytic amount of Lewis base, PPh3, initiated isomerization to provide 1,3-dienones in high yields. The introduction of a carbon-based nucleophile into the reaction mixture provided the highly efficient synthetic route to 2H-pyran-2-ones in one pot, where the carbon-based nucleophile generated by an extra equivalent of Br?nsted base, Et3N, attacked the electrophilic [3]cumulenol intermediates to initiate cyclization to give 2H-pyran-2-ones.

Regiodivergent halogenation of (E)-?2-chlorovinyl ketones via soft ?±-vinyl enolization strategy

The soft ?±-vinyl enolization of (E)-?2-chlorovinyl ketones was investigated in the presence of various halogen electrophiles. Depending on the nature of halogen electrophiles, the selective formation of three products, namely ?±,?±-dichloropropargyl keto

Ambivalent reactivity modes of β-chlorovinyl ketones: Electrophilic lithium [3]cumulenolates from soft vinyl enolization strategy

Soft spot: The soft vinyl enolization of (E)-β-chlorovinyl ketones results in the in situ generation of electrophilic lithium [3]cumulenolates, which react with nucleophiles such as another lithium [3]cumulenolate to stereoselectively form vinyl allenones

Formal metal-free γ-arylation of 1,3-dicarbonyl compounds: Via an isomerisation/1,4-addition/[3,3]-sigmatropic rearrangement sequence

A metal-free redox arylation of alkynes with sulfoxides has been developed to provide unconventional access to diverse γ-arylated 1,3-dicarbonyl compounds in an atom-economical manner. Mechanistic studies suggest that a conjugated allenone intermediate was generated in situ, which solves the problem of reactivity and regioselectivity of unsymmetrical dialkyl-substituted internal alkynes and enables the functionalisation of a broad range of substrates bearing electron-withdrawing functional groups. The resulting arylated 1,3-dicarbonyl compounds are versatile and useful building blocks for further functionalisation. This journal is

Highly regioselective synthesis of 1-acyl-5-hydroxypyrazolines or synthesis of 3,5-disubstituted pyrazoles from (E)-β-chlorovinyl ketones and benzohydrazides or hydrazine hydrate

Highly regioselective synthesis of 1-acyl-5-hydroxypyrazolines or synthesis of 3,5-disubstituted pyrazoles have been achieved through the cyclocondensation of (E)-β-chlorovinyl ketones with benzohydrazides/hydrazine hydrate under extremely mild reaction conditions. The mechanistic studies showed that diverse electrophilic pathways of (E)-β-chlorovinyl ketones could be observed by using different nucelophilic species. Moreover, the utility of the tandem reaction is further illustrated by the concise synthesis of 1-acyl-pyrazole and 3-pentyl-5-phenyl-1H-pyrazole.

A soft vinyl enolization approach to α-acylvinyl anions: Direct aldol/aldol condensation reactions of (E)-β-chlorovinyl ketones

Synthesizing the synthons: The development of α-acylvinyl anion synthons has been achieved using direct α-vinyl enolization of α,β-unsaturated ketones under mild reaction conditions. The synthetic utility of such synthons has been demonstrated in intermolecular aldol and aldol condensation reactions, which provide synthetically useful allenyl ketone and enyne derivatives. Copyright

Studies on elimination pathways of β-halovinyl ketones leading to allenyl and propargyl ketones and furans under the action of mild bases

The elimination pathway of stereochemically defined β-halovinyl ketones has been investigated using a mild base, NEt3, leading to the formation of allenyl ketones and propargyl ketones. A preferential α-vinyl enolization of (E)-β-chlorovinyl ke