16831-05-3

Basic information

• Product Name: 4-(2,4-dimethoxyphenyl)but-3-en-2-one
• Synonyms: 3-Buten-2-one,4-(2,4-dimethoxyphenyl)-;(E)-4-(2,4-dimethoxyphenyl)but-3-en-2-one
• CAS NO: 16831-05-3
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.2378
• Mol File: 16831-05-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 62 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 362.9°C at 760 mmHg
• Flash Point: 164.6°C
• Density: 1.073g/cm³
• Vapor Pressure: 1.88E-05mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: 4-(2,4-dimethoxyphenyl)but-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,4-dimethoxyphenyl)but-3-en-2-one(16831-05-3)
• EPA Substance Registry System: 4-(2,4-dimethoxyphenyl)but-3-en-2-one(16831-05-3)

Safety Data

• Hazardous Substances Data: 16831-05-3(Hazardous Substances Data)

Upstream product

• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 67-64-1 acetone 
• 16909-09-4 (E)-3-(2,4-dimethoxyphenyl)-2-propenoic acid 
• 4643-20-3 (E)-4-chloro-3-buten-2-one 
• 151-10-0 1,3-Dimethoxybenzene 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 

Downstream Products

• 1293997-24-6 (S)-tert-butyl 2-((S)-1-(2,4-dimethoxyphenyl)-3-oxobutyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 1450740-52-9 ethyl (5E)-4-hydroxy-4-methyl-6-(2,4-dimethoxyphenyl)hex-5-en-2-ynoate 
• 1450740-26-7 5-methyl-5-[(E)-2-(2,4-dimethoxyphenyl)ethenyl]-2,5-dihydrofuran-2-one 
• 1443545-72-9 (E)-1-(3,4-dihydroxyphenyl)-5-(2,4-dimethoxyphenyl)-pent-1-en-3-one 
• 1443545-66-1 acetic acid (E)-2-acetoxy-4-[5-(2,4-dimethoxyphenyl)-3-oxo-pent-1-enyl]phenyl ester 
• 1418030-42-8 6-(2,4-dimethoxyphenyl)-4-methyl-2,10-diphenyl-2,3-diazaspiro[4.5]dec-3-ene-1,8-dione 
• 1371579-07-5 (1E,4E)-1-(2,4-dimethoxyphenyl)-5-(4-nitrophenyl)penta-1,4-dien-3-one 
• 1371579-21-3 (1E,4E)-1-(2,4-dimethoxyphenyl)-5-(3-nitrophenyl)penta-1,4-dien-3-one 
• 1371579-51-9 2-bromo-N-(3-((1E,4E)-5-(2,4-dimethoxyphenyl)-3-oxopenta-1,4-dienyl)phenyl)acrylamide 
• 1371579-34-8 2-bromo-N-(4-((1E,4E)-5-(2,4-dimethoxyphenyl)-3-oxopenta-1,4-dienyl)phenyl)acrylamide 

Relevant articles and documents

Aminium cation-radical catalysed selective hydration of (E)-aryl enynes

The hydration of carbon-carbon triple bonds is an important and atom economic synthetic transformation. Herein, we report a mild and selective method for the catalytic Markovnikov hydration of (E)-aryl enynes to the corresponding enones, mediated through the bench-stable aminium salt, tris(4-bromophenyl)ammoniumyl hexachloroantimonate (TBPA). The chemoselective and diastereoselective method proceeds under neutral metal-free conditions, delivering excellent product yields from terminal and internal alkyne units. The synthesis of biologically important (E)-3-styrylisocoumarins, including a formal synthesis of the natural product achlisocoumarin III, demonstrates the utility of this novel transformation.

Stereodivergent Pd/Cu Catalysis for the Dynamic Kinetic Asymmetric Transformation of Racemic Unsymmetrical 1,3-Disubstituted Allyl Acetates

A stereodivergent Pd/Cu catalyst system has been developed for the unprecedented dynamic kinetic asymmetric transformation (DyKAT) of racemic unsymmetrical 1,3-disubstituted allylic acetates with prochiral aldimine esters. A series of α,α-disubstituted α-amino acids bearing vicinal stereocenters were easily prepared with excellent enantioselectivities (up to >99% ee) and diastereoselectivities (up to >20:1 dr). Moreover, all four stereoisomers of the product can be readily obtained simply by switching the configurations of the two chiral metal catalysts. Furthermore, the present work highlights the power of synergistic Pd/Cu catalysis consisting of two common bidentate chiral ligands for stereodivergent synthesis.

Curcumin inspired 2-chloro/phenoxy quinoline analogues: Synthesis and biological evaluation as potential anticancer agents

Synthesis of twenty new curcumin inspired 2-chloro/phenoxy quinoline derivatives is outlined in this study. The obtained new chemical entities were screened in vitro for their cytotoxic activity towards various tumor cell lines. Of the compounds screened, 6c and 9d exhibited significant activity and the most active analogue 6c displayed promising cytotoxicity against PC-3 (IC50 of 3.12 ± 0.11 μM), DU-145, NCI-H460 and 4 T1 cell lines. Further, 6c and 9d have 2.1 and 1.4 times more aqueous solubility, respectively, than curcumin. Additionally, the promising candidate 6c could induce G2/M cell cycle arrest and apoptosis in PC-3 cells, as determined by AO-EB staining, DAPI staining, analysis of ROS levels as well as annexin binding assay.