20047-49-8

Basic information

• Product Name: 2-Buten-1-one, 2-methyl-1-phenyl-, (Z)-
• Synonyms: 2-Benzoyl-trans-buten-(2);2-methyl-1-phenyl-2-buten-1-one;cis-Methylcrotophenon
• CAS NO: 20047-49-8
• Molecular Formula: C11H12O
• Molecular Weight: 160.216
• Mol File: 20047-49-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Buten-1-one, 2-methyl-1-phenyl-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Buten-1-one, 2-methyl-1-phenyl-, (Z)-(20047-49-8)
• EPA Substance Registry System: 2-Buten-1-one, 2-methyl-1-phenyl-, (Z)-(20047-49-8)

Safety Data

• Hazardous Substances Data: 20047-49-8(Hazardous Substances Data)

Upstream product

• 4461-41-0 2-chloro-but-2-ene 
• 1461-22-9 tributyltin chloride 
• 98-88-4 benzoyl chloride 
• 7204-29-7 trans-2-butenyl acetate 
• 100-51-6 benzyl alcohol 
• 6737-11-7 2-acetoxy-3-butene 
• 503-17-3 dimethylacetylene 
• 25201-44-9 2-methyl-1-phenyl-3-butene-1-ol 
• 100-52-7 benzaldehyde 
• 4111-08-4 2-hydroxy-2-methyl-butyronitrile 
• 7505-96-6 2-hydroxy-2-methyl-1-phenylbutane-1-one 
• 98-07-7 Benzotrichlorid 
• 78-93-3 butanone 
• 86633-14-9 (Z)-tributyl(1-methyl-1-propenyl)stannane 

Relevant articles and documents

Iridium-Catalyzed coupling reaction of primary alcohols with 2-alkynes leading to hydroacylation products

A novel iridium-catalyzed intermolecular coupling reaction of primary alcohols or aldehydes with 2-alkynes was successfully achieved with high regioselectivity to give hydroacylation products such as α,β- unsaturated ketones in good yields. The mechanistic investigation of the reaction strongly indicated that the coupling proceeds through the initial formation of homoallylic alcohols followed by dehydrogenation to β,γ-unsatutated ketones and then isomerisation, which leads to the hydroacylation products.

Cathodic Addition of Benzylidyne Trichloride to Ketones and Aldehydes

Ketones are converted to homologated enones 7a-g in good yields by cathodic addition of benzylidyne trichloride (1d).As intermediates α-Chlorooxiranes 6 are assumed, which rearrange via α-keto carbenium ions 9 to enones.The intermediacy of 9 is supported by the addition of 1d to norcamphor, where the products indicate equilibrating norbornyl cations as intermediates. α,β-Unsaturated ketones lead depending on steric shielding of the double bond to the cyclopropane 23 as 1,4-adduct or the enone 26 as 1,2-adduct.With aldehydes and 1d, α-chloro or βhydroxy ketones, the conversion products of 2-chlorooxiranes, are obtained.

Synthetic Utility of the Palladium-Catalyzed Coupling Reaction of Acid Chlorides with Organotins

The palladium coupling of acid chlorides with unsymmetrical organotin reagents R''3SnR' can be carried out in chloroform under mild conditions in high yields to give the ketone RCOR'in which only one of the four organic groups on tin appears in the ketone product.Alkyl partners (R''= methyl or butyl) on tin serve as anchoring groups and do not transfer.When R' is acetylenic, vinyl, aryl, methoxymethylene, allyl, or benzyl, transmetalation takes place preferentially, resulting in coupling with the acyl group from the acid chloride.The reaction is tolerant of functional groups both on the acid chloride and the tin reagent.A palladium-catalyzed coupling reaction of an organotin reagent bearing acrylate functionality with an acid chloride serves as a method to introduce both a ketone and an acrylate functionality into a carbon framework.The coupling reaction of 4-(tert-butyldiphenylsiloxy)pentanoyl chloride with benzyl 3-(tributylstannyl)acrylate gave a 71percent yield of benzyl 7-(tert-butyldiphenylsiloxy)-4-oxo-2-octenoate, a precursor to the macrolide antibiotic pyrenophorin.