436146-73-5

Basic information

• Product Name: Methanone, (2-ethynyl-1-cyclohexen-1-yl)phenyl-
• CAS NO: 436146-73-5
• Molecular Formula: C15H14O
• Molecular Weight: 210.276
• Mol File: 436146-73-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Methanone, (2-ethynyl-1-cyclohexen-1-yl)phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, (2-ethynyl-1-cyclohexen-1-yl)phenyl-(436146-73-5)
• EPA Substance Registry System: Methanone, (2-ethynyl-1-cyclohexen-1-yl)phenyl-(436146-73-5)

Safety Data

• Hazardous Substances Data: 436146-73-5(Hazardous Substances Data)

Upstream product

• 1373776-05-6 C₁₅H₁₆O 
• 21403-36-1 2-ethynyl-3,4,5,6-tetrahydrobenzaldehyde 
• 38127-47-8 2-bromocyclohex-1-ene-1-carbaldehyde 
• 439864-12-7 N-methyl N-methoxy 2-(trimethysilyl)-1-cyclohexenecarboxamide 
• 234111-16-1 2-((trimethylsilyl)ethynyl)cyclohex-1-ene-1-carbaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 

Downstream Products

• 1373775-88-2 C₂₆H₃₁NO 
• 1373775-95-1 C₂₅H₂₇NO 
• 1373775-94-0 C₂₉H₂₉NO 
• 1373776-07-8 C₂₂H₂₂O₂ 
• 1373775-98-4 C₃₅H₃₃NO 

Relevant articles and documents

Palladium-catalyzed carbene migratory insertion using conjugated ene-yne-ketones as carbene precursors

Palladium-catalyzed cross-coupling reactions between benzyl, aryl, or allyl bromides and conjugated ene-yne-ketones lead to the formation of 2-alkenyl-substituted furans. This novel coupling reaction involves oxidative addition, alkyne activation-cyclization, palladium carbene migratory insertion, β-hydride elimination, and catalyst regeneration. Palladium (2-furyl)carbene is proposed as the key intermediate, which is supported by DFT calculations. The palladium carbene character of the key intermediate is validated by three aspects, including bond lengths, Wiberg bond order indices, and molecular orbitals, by comparison to those reported for stable palladium carbene species. Computational studies also revealed that the rate-limiting step is ene-yne-ketone cyclization, which leads to the formation of the palladium (2-furyl)carbene, while the subsequent carbene migratory insertion is a facile process with a low energy barrier (5 kcal/mol).

Synthesis of 2-pyranylidene or (2-furyl)carbene-chromium complexes from conjugated enyne carbonyl compounds with Cr(CO)5(THF)

The reaction of Β-ethynyl α,β-unsaturated esters or amides with Cr(CO)5(L) (L = Et2O, THF), derived from chromium hexacarbonyl, gives 2-pyranylidene-chromium complexes in good yields. The conjugated ene-carbonyl-vinylidene complex is a key intermediate to these Fischer-type oxacarbene complexes. In contrast, β-ethynyl α,β-unsaturated ketones react with Cr(CO)5(THF) to give (2-furyl)carbene complexes via nucleophilic attack of the carbonyl oxygen atom to the intermediate π-alkyne-chromium complexes. Some chemical transformation, such as [4 + 2] type cyclization of 2-pyranylidene complexes with alkynes and aldehyde formation from (2-furyl)carbene complexes, has also been described.