1078-28-0

Usage

Uses

Used in Chemical Synthesis:
6-Methoxyquinaldine is used as a starting reagent for the synthesis of various tetrahydroquinoline derivatives, which are important in the development of pharmaceuticals and other chemical compounds.
Used in Fluorescent Probes:
6-Methoxyquinaldine is used as a key component in the preparation and characterization of three RNA-specific fluorescent probes (E36, E144, and F22). These probes are designed for applications in live cell imaging, allowing for the visualization and study of RNA dynamics within cells.
Used in Live Cell Imaging:
In the field of cell biology, 6-Methoxyquinaldine is used as a component in the development of RNA-specific fluorescent probes that enable live cell imaging. This application aids researchers in understanding the behavior and interactions of RNA within living cells, which is crucial for advancing our knowledge of cellular processes and potential therapeutic targets.

InChI:InChI=1/C11H11NO/c1-8-3-4-9-7-10(13-2)5-6-11(9)12-8/h3-7H,1-2H3

Upstream product

• 111-34-2 -butyl vinyl ether 
• 20265-97-8 p-anisidine hydrochloride 
• 104-94-9 4-methoxy-aniline 
• 74-86-2 acetylene 
• 123-73-9 crotonaldehyde 
• 5470-34-8 4-methoxyformanilide 
• 123-63-7 paracetaldehyde 
• 877-42-9 6-Bromo-2-methyl-quinoline 
• 123-73-9 trans-Crotonaldehyde 
• 52271-43-9 4-(4-methoxyphenyl)-2-butanone oxime 
• 74-87-3 methylene chloride 
• 74-88-4 methyl iodide 
• 108-88-3 toluene 
• 64-17-5 ethanol 

Downstream Products

• 59066-58-9 (E)-6-methoxy-2-styrylquinoline 
• 108716-85-4 (E)-6-methoxy-2-(4-methoxystyryl)quinoline 
• 102237-85-4 2-(3,4-dimethoxy-trans-styryl)-6-methoxy-quinoline 
• 89060-22-0 6-methoxyquinoline-2-carboxaldehyde 
• 83719-91-9 2-(6-methoxyquinolin-2-yl)-1-phenylethanone 
• 84689-22-5 2,4,6-Trimethyl-benzenesulfonate1-amino-6-methoxy-2-methyl-quinolinium; 
• 99540-15-5 4-(3'-methoxyphenyl)-N,N-dimethyl-2-butanamine 
• 1608092-48-3 6-methoxy-2-((2-phenyl-1,2,3,4-tetrahydroisoquinoline-1-yl)methyl)quinoline 

Relevant academic research and scientific papers

Aerobic oxidative dehydrogenation of N-heterocycles catalyzed by cobalt porphyrin

An efficient catalytic procedure has been developed for the aerobic oxidative dehydrogenation of N-heterocycles by cobalt porphyrin in the absence of any additives. The catalytic system could tolerate various 1,2,3,4-tetrahydroquinoline derivatives and some other N-heterocycles. The corresponding N-heteroaromatics could be obtained in 59–86% yields. The mechanism investigation suggested that the aerobic oxidative dehydrogenation might proceed with imine intermediate through radical paths.

Catalytic Asymmetric Cascade Using Spiro-Pyrrolidine Organocatalyst: Efficient Construction of Hydrophenanthridine Derivatives

A newly developed SPD (spiro-pyrrolidine) organocatalyst has been demonstrated to enable an asymmetric aza-Michael/Michael/aldol cyclization cascade, in which two six-membered rings (B/C) and three stereocenters have been constructed in a catalytic one-step process. It is so far the most efficient method for construction of hydrophenanthridine derivatives featuring high enantioselectivity. The trans- or cis-fused B/C-rings can be selectively assembled in a substrate-controlled manner. Moreover, this cascade could magnify to gram scale without loss of enanioselectivity.

Continuous Flow Doebner-Miller Reaction and Isolation Using Continuous Stirred Tank Reactors

Continuous flow Doebner-Miller synthesis of different quinaldines from respective anilines is demonstrated using sulfuric acid as a homogeneous catalyst. The extent of reaction was monitored for various parameters, namely, temperature, residence time, mole ratio of sulfuric acid to substrate, mole ratio of crotonaldehyde to substrate, and so forth. Continuous stirred reactors in series were used as a preferred configuration for this rection that generates byproduct in the form of sticky solid material. The approach has been extended for six different anilines, and the results are compared with batch reactions. Continuous stirred reactors in series with distributed dosing of crotonaldehyde facilitated a continuous flow reaction with lower byproduct formation, increased yields, and continuous workup and is a scalable approach.

Discovery of fused heterocyclic carboxamide derivatives as novel α7-nAChR agonists: Synthesis, preliminary SAR and biological evaluation

The α7 nicotinic acetylcholine receptor (α7 nAChR) has emerged as a promising therapeutic target for schizophrenia. In our previous work, a novel series of α7-nAChR agonists bearing scaffold of indolizine were discovered. To explore the effect of aromaticity on the activity and find more active agents, herein, fused heterocyclic carboxamide derivatives were designed and synthesized in this study. Based on the evaluation by two-electrode voltage clamp in Xenopus oocytes, 27 of the synthesized compounds showed obvious agonism of α7 nAChR. Particularly, compounds 10a and 10e showed significantly higher Emax than EVP-6124. The result illustrated the importance of aromaticity to the activity of agonism. Compound 10a, which showed EC50 of 1.88 μM and Emax of 72.4%, was further characterized comprehensively, including co-application with type II positive allosteric modulator PNU-120596, selectivity with other closely related ligand-gated ion channel, etc. The results showed that 10a showed moderate selectivity over other subtypes such as α4β2 and α3β4 nAChR. 10a evoked α7-like currents that were inhibited by MLA and enhanced in the presence of the α7 PAM PNU-120596. The analysis of binding mode and understanding of structure-activity relationship provided insights to develop more potent novel α7-nAChR agonists.

Synthesis and structure elucidation of allyl Pd(II) complexes of NHC ligands derived from substituted imidazo[1,5-a]quinolin-1(2H)-ylidene

Nine Pd(II) complexes involving N-heterocyclic carbenes (NHCs) derived from 2-substituted and 2- and 7-substituted imidazo[1,5-a]quinolin-1(2H)-ylidene with auxiliary allylic ligands were synthesized and characterized. The structure and configuration of the complexes were elucidated on the basis of combination of dynamic NMR and DFT studies. Conformational studies in respect of hindered rotation around Pd-C bond and η3-η1-η3 pseudo allyl rotation were performed. The results from dynamic NMR and DFT studies confirmed the mechanism of selective η3-η1-η3 isomerization, whose energy barriers are affected by steric hindrance of substituents at nitrogen atom. Energy barriers of isomerization (16.7–18.8 kcal/mol) are slightly influenced by the electronic nature of substituents at seventh position in imidazo[1,5-a]quinolin-1(2H)-ylidene moiety. The results from DFT calculations were in good agreement with the experimental energy barriers.

Synthesis of 2,3-disubstituted quinolines from in situ generated imines and its enamine tautomer under radical cation induced conditions

A tandem cyclization/aromatization of anilines and aldehydes was achieved under catalytic radical cation salt induced conditions, producing a series of 2,3-disubstituted quinolines in good yields. In this reaction, the in situ generated imine tautomerizes to enamine, which acts as a dienophile to participate in the tandem cyclization, and further elimination of the anilino group triggers the aromatization of tetrahydroquinolines, avoiding harsh conditions.

A highly selective and easy-to-synthesize Zn(II) fluorescent probe based on 6-methoxyquinolin

A novel fluorescent Zn2+ probe based on 6-methoxyquinolin was synthesized in four steps from inexpensive starting materials. It exhibits very strong fluorescence responses and has a remarkably high selectivity to Zn 2+ than other physiological relevant metal ions. This new compound could be used as low-priced yet high-quality Zn2+ probe.

Deracemization of Phenyl-Substituted 2-Methyl-1,2,3,4-Tetrahydroquinolines by a Recombinant Monoamine Oxidase from Pseudomonas monteilii ZMU-T01

A monoamine oxidase (MAO5) from Pseudomonas monteilii ZMU-T01 was first heterologously expressed in Escherichia coli BL21(DE3) and then used as a biocatalyst for the deracemization of racemic 2-methyl-1,2,3,4-tetrahdroquinoline derivatives to yield the unreacted R enantiomer with up to >99 % ee. Sequence alignment revealed that MAO5 shared 14.7 % identity toward the well-studied monoamine oxidase (MAO-N).

A water soluble ratiometric fluorescent probe for targeting SO2in mitochondria based on conjugated biquinolines

Despite the unprecedented development of SO2 fluorescent probes in the past five years, the water-solubility of these probes is still an important factor related to their practical application. In previous work, we have studied SO2 detection by coupling quinoline and coumarin. Although the water solubility of the probe was improved, SO2 detection in a 100% aqueous medium was not fully achieved. Therefore, based on the previous system, we conjugated two quinolines to realize a 100% water-soluble sulfur dioxide fluorescent probe. The Probe showed a large Stokes shift (170 nm). Besides, the Probe could respond to SO2 within 1.5 min with high selectivity and sensitivity (LOD = 0.29 μM). In addition, fluorescence co-localization studies suggested that the Probe could be used for monitoring SO2 in the mitochondria of HeLa cells and living mice. It is believed that such an excellent probe will have a wide application prospect in the future. This journal is

Limitations of the two-phase doebner-miller reaction for the synthesis of quinolines

The Doebner-Miller synthesis of quinolines under modified biphasic conditions was investigated. Crotonaldehyde, reacted readily with aniline to produce 2-methylquinoline. However, cinnamaldehyde and other γ-substituted α,β-unsaturated aldehydes yielded complex mixtures with substituted anilines to provide only trace quantities of quinolines. The Doebner-Miller reaction under these conditions is only suitable for sterically accessible α,β-unsaturated aldehydes.