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

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 
• 69731-27-7 (E)-1-bromo-2-(3,4-dimethoxyphenyl)ethene 
• 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 
• 5344-90-1 2-Aminobenzyl alcohol 
• 15001-27-1 O-methyldehydrozingerone 
• 109-92-2 ethyl vinyl ether 
• 91-22-5 quinoline 

Downstream Products

• 95279-34-8 2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-quinoline 
• 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 

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

Ru(II)–NNO pincer-type complexes catalysed E-olefination of alkyl-substituted quinolines/pyrazines utilizing primary alcohols

An efficient and selective E-olefination of alkyl-substituted quinolines and pyrazines through acceptorless dehydrogenative coupling of alcohols catalysed by Ru(II)–N^N^O pincer-type complexes encompassing carbonyl and triphenylarsines as co-ligands is de

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.

A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction

The present study describes the total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, in three steps and high yields (78%, 76%, 74%, and 66%, respectively) from common aldehyde and the ylide respectives. The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium (aq. NaOH/CH2Cl2 1:1 or t-BuOK/t-BuOH/CH2Cl2 1:1), affording olefinic intermediates in high yields.

Direct alkenylation of 2-substituted azaarenes with carbonyls via C-H bond activation using iron-based metal-organic framework Fe3O(BPDC)3 as an efficient heterogeneous catalyst

A porous crystalline metal-organic framework Fe3O(BPDC)3 was synthesized from the reaction of biphenyl-4,4′-dicarboxylic acid and iron(III) chloride hexahydrate by a solvothermal method in the presence of acetic acid, and was characterized by using a variety of different techniques. The Fe3O(BPDC)3 could be used as an efficient heterogeneous catalyst in the synthesis of 2-alkenylazaarenes using the direct alkenylation of 2-substituted azaarenes with carbonyls via C-H bond activation. The presence of acetic acid as a co-catalyst accelerated the transformation significantly. The Fe3O(BPDC)3 exhibited better performance in this transformation then other MOFs such as Fe3O(BDC)3, Cu2(OBA)2(BPY), Cu2(BDC)2(DABCO), Ni2(BDC)2(DABCO), Zn-MOF-74, and Cu2(NDC)2(DABCO). The Fe3O(BPDC)3 also exhibited higher catalytic activity than that of several homogeneous catalysts such as FeCl2, FeCl3, CuCl2, Zn(OAc)2, Zn(NO3)2, and Ni(OAc)2. The Fe3O(BPDC)3 catalyst could be recovered and reused several times in the synthesis of 2-alkenylazaarenes without a significant degradation in catalytic activity. To the best of our knowledge, 2-alkenylazaarenes was not previously synthesized via the direct alkenylation of 2-substituted azaarenes with carbonyls using heterogeneous catalysts.

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.

Regiospecific C-N photocyclization of 2-styrylquinolines

Regiospecific C-N photocyclization of 2-styrylquinolines resulting in formation of potentially biologically active quino[1,2-a]quinolizinium derivatives was investigated. The presence of strong electron-donating groups in the phenyl ring reveals to be a crucial factor managing photocyclization effectiveness. Introduction of a crown ether moiety allows changing the photoreaction parameters by means of complexation with Mg(ClO4) 2.

Multifunctional catalysis of a ruthenium-grafted hydrotalcite: One-pot synthesis of quinolines from 2-aminobenzyl alcohol and various carbonyl compounds via aerobic oxidation and aldol reaction

The Ru-grafted hydrotalcite was found to be an excellent multifunctional catalyst for one-pot synthesis of quinolines from 2-aminobenzyl alcohol and various carbonyl compounds. These quinolines were obtained through aerobic oxidation by the Ru species, followed by aldol reaction on base sites of the hydrotalcite.

APPLICATION OF THE LEWIS ACID CATALYZED CYCLOADDITION REACTION TO SYNTHESIS OF NATURAL QUINOLINE ALKALOIDS

Lewis acids catalyzed cycloaddition reaction of the Schiff base with the olefin was applied to the syntheses of some natural quinoline alkaloids.The extension of cycloaddition using the acetal and the orthoester as dienophiles or using s-triazin

A SIMPLE REGIOSELECTIVE PREPARATION OF 2- OR 3-SUBSTITUTED QUINOLINE DERIVATIVES VIA DIALKYLQUINOLYLBORANES

Various quinoline derivatives possessing a substituent at the 2- or 3-position were prepared by the reaction of dialkylquinolylboranes and organic bromides in the presence of a palladium catalyst.