50552-30-2

Basic information

• Product Name: 4-phenylhex-5-en-2-one
• Synonyms: 4-Phenylhex-5-en-2-one; 5-hexen-2-one, 4-phenyl-
• CAS NO: 50552-30-2
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.239
• Mol File: 50552-30-2.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 257.6°C at 760 mmHg
• Flash Point: 108.1°C
• Density: 0.961g/cm³
• Vapor Pressure: 0.0144mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: 4-phenylhex-5-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-phenylhex-5-en-2-one(50552-30-2)
• EPA Substance Registry System: 4-phenylhex-5-en-2-one(50552-30-2)

Safety Data

• Hazardous Substances Data: 50552-30-2(Hazardous Substances Data)

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 67-64-1 acetone 
• 121725-72-2 2-acetyl-3-phenyl-pent-4-enoic acid methyl ester 
• 1826-67-1 vinyl magnesium bromide 
• 1896-62-4 (E)-benzalacetone 
• 541-50-4 2-acetoacetic acid 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 116-11-0 2-Methoxypropene 
• 2327-99-3 1-phenylpropadiene 
• 117747-28-1 C₆H₁₃NO 
• 2687-12-9 cinnamyl chloride 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 137151-62-3 (E)-1-phenyl-3-isopropenyloxyprop-1-ene 
• 112163-00-5 (+/-)-1-phenylallyl acetoacetate 

Downstream Products

• 16460-85-8 (R)-4-phenylhexan-2-one 
• 60091-38-5 4-phenyl-5-hexen-2-ol 
• 88681-86-1 3-Oxo-5-phenyl-hept-6-enoic acid methyl ester 

Relevant articles and documents

Rhodium-Catalyzed Branched and Enantioselective Direct α-Allylic Alkylation of Simple Ketones with Alkynes

Herein, we report the first direct branched-selective α-allylic alkylation of simple ketones with alkynes under rhodium and secondary amine cooperative catalysis. Through a rhodium-hydride-catalyzed allylic substitution pathway, a series of valuable γ,δ-unsaturated ketones are obtained with excellent regioselectivity in an atom-economic and byproduct-free manner. With a chiral BIPHEP ligand, high enantioselectivity has been achieved for this transformation.

Regioselective Rhodium-Catalyzed Addition of β-Keto Esters, β-Keto Amides, and 1,3-Diketones to Internal Alkynes

The first rhodium-catalyzed regioselective addition of 1,3-dicarbonyl compounds, including β-keto esters, β-keto amides, and 1,3-diketones, to internal alkynes furnishes branched allylic compounds. By applying RhI/DPEphos/TFA as the catalytic system, aliphatic as well as aromatic internal methyl-substituted alkynes act as suitable substrates to yield valuable branched α-allylated 1,3-dicarbonyl compounds regioselectively in good to excellent yields. A simple basic saponification–decarboxylation procedure provides access to valuable γ,δ-unsaturated ketones. The reaction shows a broad functional-group tolerance, and numerous structural variations on both reaction partners highlight the synthetic potential and flexibility of this method.

Rhodium-catalyzed chemo- and regioselective decarboxylative addition of β-ketoacids to alkynes

A highly efficient rhodium-catalyzed chemo- and regioselective addition of β-ketoacids to alkynes is reported. Applying a Rh(i)/(S,S)-DIOP catalyst system, γ,δ-unsaturated ketones were prepared with exclusively branched selectivity under mild conditions. This demonstrates that readily available alkynes can be an alternative entry to allyl electrophiles in transition-metal catalyzed allylic alkylation reactions.