57542-05-9

Basic information

• Product Name: 4-Hexen-1-one, 1-phenyl-, (4E)-
• CAS NO: 57542-05-9
• Molecular Formula: C12H14O
• Molecular Weight: 174.243
• Mol File: 57542-05-9.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 4-Hexen-1-one, 1-phenyl-, (4E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hexen-1-one, 1-phenyl-, (4E)-(57542-05-9)
• EPA Substance Registry System: 4-Hexen-1-one, 1-phenyl-, (4E)-(57542-05-9)

Safety Data

• Hazardous Substances Data: 57542-05-9(Hazardous Substances Data)

Upstream product

• 17851-98-8 1-phenyl-1-(tributylstannyloxy)ethene 
• 591-97-9 1-chloro-2-butene 
• 542-72-3 (E)-but-2-en-1-ol 
• 532-27-4 1-chloroacetophenone 
• 106-99-0 buta-1,3-diene 
• 98-86-2 acetophenone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 504-61-0 (E)-but-2-enol 
• 4784-77-4 (E/Z)-crotyl bromide 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 4535-44-8 (E)-1-phenylhex-4-ene-1-ol 
• 65001-62-9 3-buten-2-yl benzoate 
• 3240-29-7 1-Phenylpent-4-en-1-one 

Downstream Products

• 59361-03-4 (E)-2-phenylhept-5-en-2-ol 
• 4535-44-8 (E)-1-phenylhex-4-ene-1-ol 
• 182144-39-4 C₁₂H₁₅O 
• 139909-12-9 6-Chloro-6-phenyl-2-hexene 
• 59321-58-3 1-Phenyl-4-hexen-1-ol 

Relevant articles and documents

Selective Synthesis of Z-Silyl Enol Ethers via Ni-Catalyzed Remote Functionalization of Ketones

We report a remote functionalization strategy, which allows the Z-selective synthesis of silyl enol ethers of (hetero)aromatic and aliphatic ketones via Ni-catalyzed chain walking from a distant olefin site. The positional selectivity is controlled by the directionality of the chain walk and is independent of thermodynamic preferences of the resulting silyl enol ether. Our mechanistic data indicate that a Ni(I) dimer is formed under these conditions, which serves as a catalyst resting state and, upon reaction with an alkyl bromide, is converted to [Ni(II)-H] as an active chain-walking/functionalization catalyst, ultimately generating a stabilized η3-bound Ni(II) enolate as the key selectivity-controlling intermediate.

Water-Accelerated Nickel-Catalyzed α-Crotylation of Simple Ketones with 1,3-Butadiene under pH and Redox-Neutral Conditions

We report a nickel/NHC-catalyzed branched-selective α-crotylation of simple ketones using 1,3-butadiene as the alkylation agent. This reaction is regioselective and operated under pH and redox-neutral conditions. Water was used as the sole additive, which significantly accelerates the transformation.

Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the SRN1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.