155586-41-7

Basic information

• Product Name: 1-(3,4-Dimethoxy-phenyl)-buta-2,3-dien-1-one
• Synonyms: 1-(3,4-Dimethoxy-phenyl)-buta-2,3-dien-1-one
• CAS NO: 155586-41-7
• Molecular Weight: 204.225
• Mol File: 155586-41-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-(3,4-Dimethoxy-phenyl)-buta-2,3-dien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-Dimethoxy-phenyl)-buta-2,3-dien-1-one(155586-41-7)
• EPA Substance Registry System: 1-(3,4-Dimethoxy-phenyl)-buta-2,3-dien-1-one(155586-41-7)

Safety Data

• Hazardous Substances Data: 155586-41-7(Hazardous Substances Data)

Usage

Molecular weight

204.22 g/mol

Physical state

Yellowish crystalline solid

Family

Chalcone family

Research and pharmaceutical applications

Potential pharmacological properties

Pharmacological properties

Anti-inflammatory, antioxidant, and anticancer effects

Additional properties

Antimicrobial and antidiabetic potential

Interest in medicinal chemistry

Further investigation and development due to its various properties

Upstream product

• 91496-51-4 1-(3,4-dimethoxy-phenyl)-but-3-yn-1-ol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 64-19-7 acetic acid 
• 18295-60-8 propargyl magnesium bromide 
• 155586-38-2 N,3,4-trimethoxy-N-methylbenzamide 

Downstream Products

• 1332524-45-4 3-cyano-1-(3,4-dimethoxybenzoyl)-4-(3,4-dimethoxyphenyl)-2,6-dimethylbenzene 
• 1590402-54-2 (3-benzoyl-2-methylindolizin-1-yl)(3,4-dimethoxyphenyl)methanone 
• 1580528-93-3 7-(3,4-dimethoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine 
• 15001-27-1 O-methyldehydrozingerone 
• 1454271-71-6 (E)-1-(3,4-dimethoxyphenyl)-3-fluorobut-2-en-1-one 
• 1454271-90-9 (Z)-1-(3,4-dimethoxyphenyl)-3-fluorobut-2-en-1-one 
• 1432479-29-2 C₁₈H₂₀O₆ 
• 1394836-53-3 C₁₉H₁₈N₂O₃ 
• 1350307-62-8 2-aceto-1-(3,4-dimethoxyphenyl)-4-phenylbutane-1,4-dione 
• 36517-91-6 2,3-dihydro-5,6-dimethoxy-1H-indene-1,3-dione 
• 109384-28-3 2-(3,4-Dimethoxy-phenyl)-furan 

Relevant articles and documents

Tandem reactions of 1,2-allenic ketones leading to substituted benzenes and α,β-unsaturated nitriles

One-pot double Michael addition/intramolecular aldol reaction/ decarboxylation of 1,2-allenic ketones with cyanoacetate offers an efficient and convenient approach to highly functionalized benzenes. With 2-substituted cyanoacetates, the reaction proceeds via a different tandem process to afford α,β-unsaturated nitriles effectively.

C-C-Bond Formation by the Palladium-Catalyzed Cycloisomerization/Dimerization of Terminal Allenyl Ketones: Selectivity and Mechanistic Aspects

The scope of the palladium-catalyzed cyclization/dimerization of terminal allenyl ketones 1 to the 2,4-disubstituted furans 3 has been investigated. Simplified and improved conditions almost exclusively provided the dimer 3, accompanied by only traces of the easily separable monomer 2. The formation of an isomer of 3, the unconjugated ketone 4, was completeley suppressed. Under these mild conditions, besides the normal functional group tolerance known for palladium-catalyzed reactions, an interesting selectivity was observed with functional groups that are known to react either in palladium-catalyzed reactions or reactions catalyzed by other transition-metals. Thus aryl halides, terminal alkynes, 1,6-enynes, and α-allenic alcohols were tolerated. In the latter example the selective reaction of only one out of two different allenes was achieved. Mechanistic investigation indicated a Pd(II)/Pd(IV)-cycle involving palladium(II)-γ-alkoxyvinylcarbene and furylpalladium(IV) hydride intermediates, although a second pathway for the formation of the dimer 3 which also involves Pd(IV)-intermediates like the 3,4-dimethylenepalladacyclopentane 23 and the 3-methylenepalladacyclobutane-like structure 15 (respectively 25) could not completely be excluded.