86395-64-4

Upstream product

• 148601-11-0 (2E,4E)-4-methyl-5-phenyl-penta-2,4-dien-1-ol 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 
• 75-07-0 acetaldehyde 

Downstream Products

• 1379586-75-0 5,5-dimethyl-2-[(2E,4E)-4-methyl-5-phenylpenta-2,4-dien-1-ylidene]cyclohexane-1,3-dione 
• 1379586-70-5 3-(4-methyl-5-phenyl-penta-2,4-dienylidene)-pentane-2,4-dione 
• 50397-92-7 3-methyl-2-phenylcyclopent-2-en-1-one 

Relevant academic research and scientific papers

One-pot organocatalytic tandem aldol/polycyclization reactions between 1,3-dicarbonyl compounds and α,β,γ,δ-unsaturated aldehydes for the straightforward assembly of cyclopenta[b]furan-type derivatives: New insight into the Knoevenagel reaction

A new cascade pathway viable for Knoevenagel chemistry that involves the coupling between 1,3-dicarbonyl systems and α,β,γ,δ- unsaturated aldehydes has been developed. The process comprises the combination of a classic aldol-type condensation and a rare spontaneous metal-free cycloisomerization, representing a convergent and innovative approach for the stereoselective synthesis of cyclopenta[b]furan-type derivatives. The scope and limitations with respect to both reaction partners and mechanistic features were investigated. Meaningfully, our study provides valuable guidance concerning the structural and electronic effects controlling the reactivity of conjugated polyene carbonyl systems. Copyright

Synthesis and hydrolysis of [alkenyl(alkoxy)carbene]manganese complexes: Evidence for a transient allylic intermediate on the way to α,β-unsaturated aldehydes

A variety of alkenylcarbene complexes [Cp'(CO)2Mn= C(OEt)CH=CHR] (3) (Cp' = TiS-MeCsH4) was obtained in a straightforward manner upon aldol condensation of [Cp'(CO)2Mn=C(OEt)CH3] (1) with aromatic and α,β- unsaturated aldehydes RC(H)O (2). The reaction is totally stereoselective, giving (E)- or (all-E)-alkenylcarbenes only. The protonation of 3 at low temperature followed by reaction with water affords the α,β-unsaturated aldehyde complexes [Cp'(CO)2Mn(n2-RCH=CHCHO] (5), from which the aldehydes RC(H)=C(H)C(H)O (6) were displaced by acetonitrile. The intermediate aldehyde complexes are shown to result from the hydrolysis of a transient cationic π- allyl species [Cp'(CO)2Mn(n3-RCHCHC(OEt)H]+ ([4]+) formed upon protonation of 3.