53744-27-7

Basic information

• Product Name: 3-(3,4-dimethoxyphenyl)-1-phenylprop-2-en-1-one
• CAS NO: 53744-27-7
• Molecular Formula: C₁₇H₁₆O₃
• Molecular Weight: 268.3071
• Mol File: 53744-27-7.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 421.8°C at 760 mmHg
• Flash Point: 200.7°C
• Density: 1.128g/cm³
• Vapor Pressure: 2.53E-07mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 3-(3,4-dimethoxyphenyl)-1-phenylprop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3,4-dimethoxyphenyl)-1-phenylprop-2-en-1-one(53744-27-7)
• EPA Substance Registry System: 3-(3,4-dimethoxyphenyl)-1-phenylprop-2-en-1-one(53744-27-7)

Safety Data

• Hazardous Substances Data: 53744-27-7(Hazardous Substances Data)

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 98-86-2 acetophenone 
• 1352347-01-3 (E)-1-(2-chlorophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 1136-86-3 methyl (3,4,5-trimethoxyphenyl) ketone 

Downstream Products

• 49747-52-6 1-(3,4-dimethoxyphenyl)-3-phenylpropan-1-one 
• 7468-58-8 3-(3, 4-dimethoxyphenyl)-1-phenylpropan-1-one 
• 72666-42-3 4-(3,4-Dimethoxy-phenyl)-2-phenyl-6-p-tolyl-pyridine 
• 72666-49-0 2-(4-Chloro-phenyl)-4-(3,4-dimethoxy-phenyl)-6-phenyl-pyridine 
• 79852-76-9 4-(3,4-Dimethoxy-phenyl)-2-(3-nitro-phenyl)-6-phenyl-pyridine 
• 160729-09-9 2-amino-4-(3,4-dimethoxy-phenyl)-6-phenyl-3-pyridinecarbonitrile 
• 128566-86-9 ethyl 2-acetyl-3-(3,4-dimethoxyphenyl)-5-phenyl-5-oxovalerate 
• 1042093-16-2 2-amino-5-(3,4-dimethoxyphenyl)-7-phenyl-5,8-dihydropyrido[2,3-d]pyrimidin-4(3H)-one 
• 1197386-10-9 2-(p-tolylthio)-4-(3,4-dimethoxyphenyl)-6-phenylpyridine-3-carbonitrile 
• 1204142-11-9 3-(3,4-dimethoxyphenyl)-4-nitro-1-phenylbutan-1-one 
• 1298097-00-3 (benzofuran-2-yl)(4,5-dihydro-5-(3,4-dimethoxyphenyl)-3-phenylpyrazol-1-yl)methanone 
• 1372629-98-5 2-(8,9-dimethoxy-6H-benzo[c]chromen-6-yl)-1-phenylethanone 
• 60246-78-8 2-(3,4-dimethoxy-phenyl)-4-phenyl-2,3-dihydro-benzo[b][1,4]thiazepine 
• 1429405-47-9 1-[2-(5-chloro-2-benzoxazolinone-3-yl)acetyl]-3-phenyl-5-(3,4-dimethoxyphenyl)-4,5-dihydro-(1H)-pyrazole 

Relevant articles and documents

Absolute configuration and biological profile of pyrazoline enantiomers as MAO inhibitory activity

A new racemic pyrazoline derivative was synthesized and resolved to its enantiomers using analytic and semipreparative high-pressure liquid chromatography. The absolute configuration of both fractions was established using vibrational circular dichroism.

Inhibition of Caco-2 and MCF-7 cancer cells using chalcones: synthesis, biological evaluation and computational study

Cancer is the second death cause worldwide, with breast and colon cancer among the most prevalent types. Traditional treatment strategies have several side effects that inspire the development of novel anticancer agents derived from natural sources, like chalcone derivatives. For this investigation, twenty-three chalcones (4a-w) were synthesized and evaluated as antiproliferative agents against MCF-7 and Caco-2 cells, finding three and two compounds with similar or higher antiproliferative activity than daunorubicin, while only two chalcones showed better selectivity indexes than daunorubicin on MCF-7. From these results, we developed good-performance QSAR models (r > 0.850, q2>0.650), finding several structural features that could modify chalcone activity and selectivity. According to these models, chalcones 4w and 4t have high potency and selectivity against Caco-2 and MCF-7, respectively, which make them attractive candidates for hit-to-lead development of ROS-independent pro apoptotic agents.

Rapid umpolung Michael addition of isatin N, N ′-cyclic azomethine imine 1,3-dipoles with chalcones

The umpolung Michael addition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones is reported. The reaction could be finished within a very short time (0.3-2 min), with 3,3-disubstituted oxindole derivatives obtained in moderate to excellent yields with promising dr values. Unusual Michael adducts were obtained in moderate to high yields (26-98%) with low to high diastereoselectivities (0.8: 1 to 8.5: 1 dr). All the synthesized compounds (3, 3′, 4, 5, 5′, 7, 7′, 9 and 9′) were well characterized by FTIR, NMR, and mass spectral analyses and further confirmed by the single-crystal X-ray diffraction analysis of compounds 3aa and 4n.