77669-22-8

Basic information

• Product Name: 2-(3,4-dimethoxyphenylethenyl)quinoline
• Synonyms: 2-(3,4-dimethoxyphenylethenyl)quinoline
• CAS NO: 77669-22-8
• Molecular Weight: 291.349
• Mol File: 77669-22-8.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 2-(3,4-dimethoxyphenylethenyl)quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-dimethoxyphenylethenyl)quinoline(77669-22-8)
• EPA Substance Registry System: 2-(3,4-dimethoxyphenylethenyl)quinoline(77669-22-8)

Safety Data

• Hazardous Substances Data: 77669-22-8(Hazardous Substances Data)

Upstream product

• 91-63-4 2-methylquinoline 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 5344-90-1 2-Aminobenzyl alcohol 
• 15001-27-1 O-methyldehydrozingerone 
• 91-22-5 quinoline 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 5470-96-2 quinoline 2-carbaldehyde 
• 93-10-7 quinoline-2-carboxylic acid 
• 1613-37-2 Quinoline N-oxide 
• 6380-23-0 3,4-dimethoxystyrene 
• 62-53-3 aniline 
• 58045-88-8 3,4-dimethoxycinnamaldehyde 
• 109-92-2 ethyl vinyl ether 
• 69731-27-7 (E)-1-bromo-2-(3,4-dimethoxyphenyl)ethene 

Downstream Products

• 442-33-1 (-)-(2S)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1-methyl-1,2,3,4-tetrahydroquinoline 
• 104967-55-7 2-[2-(3,4-dimethoxyphenyl)ethyl]-1-methyl-1,2,3,4-tetrahydroquinolineanol 
• 104967-54-6 2-(3,4-dimethoxy-β-phenethyl)-1,2,3,4-tetrahydroquinoline 
• 95279-34-8 2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-quinoline 

Relevant articles and documents

Biological evaluation of substituted quinolines

Several quinolines were synthesized and evaluated in vitro against several parasites (Trypanosoma brucei, T. cruzi, Leishmania infantum, L. amazonensis, Plasmodium falciparum). Then, they were evaluated in vitro (at 10μM), against HTLV-1 transformed cells

Metal-Free Synthesis of Alkenylazaarenes and 2-Aminoquinolines through Base-Mediated Aerobic Oxidative Dehydrogenation of Benzyl Alcohols

A metal-free, base-mediated, and atom-efficient oxidative dehydrogenative coupling of substituted phenylmethanols (benzyl alcohols) with methyl azaarenes or phenylacetonitriles to afford substituted alkenylazaarenes or 2-aminoquinolines, respectively is described. CsOH.H2O was discovered to be the base of choice for obtaining optimal yields of the title compounds, although the reaction could proceed with KOH as well. The protocol that works efficiently in the presence of air is amenable over broad range of substrates.

C2-Alkenylation of N-heteroaromatic compounds: Via Br?nsted acid catalysis

Substituted heteroaromatic compounds, especially those based on pyridine, hold a privileged position within drug discovery and medicinal chemistry. However, functionalisation of the C2 position of 6-membered heteroarenes is challenging because of (a) the difficulties of installing a halogen at this site and (b) the instability of C2 heteroaryl-metal reagents. Here we show that C2-alkenylated heteroaromatics can be accessed by simple Br?nsted acid catalysed union of diverse heteroarene N-oxides with alkenes. The approach is notable because (a) it is operationally simple, (b) the Br?nsted acid catalyst is cheap, non-toxic and sustainable, (c) the N-oxide activator disappears during the reaction, and (d) water is the sole stoichiometric byproduct of the process. The new protocol offers orthogonal functional group tolerance to metal-catalysed methods and can be integrated easily into synthetic sequences to provide polyfunctionalised targets. In broader terms, this study demonstrates how classical organic reactivity can still be used to provide solutions to contemporary synthetic challenges that might otherwise be approached using transition metal catalysis.