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Usage

Uses

Used in Pharmaceutical Industry:
2,6-Dimethylquinoline is used as a research chemical for in vitro studies, specifically to evaluate its inhibitory effects on the recombinant human CYP2B6 enzyme. This application aids in understanding the enzyme's role in drug metabolism and the potential interactions with other chemicals.
Used in Research and Development:
2,6-Dimethylquinoline serves as a valuable compound in the development of new drugs and therapies. Its study helps researchers to identify potential drug candidates and understand their interactions with specific enzymes, which is crucial for drug discovery and optimization processes.

Biochem/physiol Actions

2,6-Dimethylquinoline is the chemical constituent present in roots of Peucedantu praeruptorum. It is a potential inhibitor of cytochrome P450 1A2 activity.

InChI:InChI=1/C11H11N/c1-8-3-6-11-10(7-8)5-4-9(2)12-11/h3-7H,1-2H3

Upstream product

• 3085-54-9 N-(4-methylphenyl)formamide 
• 625-34-3 3-oxobutyraldehyde 
• 106-49-0 p-toluidine 
• 111-34-2 -butyl vinyl ether 
• 540-23-8 p-toluidine hydrochloride 
• 74-86-2 acetylene 
• 123-73-9 crotonaldehyde 
• 7647-01-0 hydrogenchloride 
• 123-63-7 paracetaldehyde 
• 67-64-1 acetone 
• 170697-87-7 (+/-)-cis-4-ethoxy-2,6-dimethyl-1,2,3,4-tetrahydroquinoline 
• 99-99-0 1-methyl-4-nitrobenzene 
• 75-07-0 acetaldehyde 
• 64-17-5 ethanol 

Downstream Products

• 83719-89-5 2-(6-methylquinolin-2-yl)-1-phenylethanone 
• 1028310-40-8 Acetic acid 3-[(E)-2-(6-methyl-quinolin-2-yl)-vinyl]-phenyl ester 
• 84689-26-9 2,4,6-Trimethyl-benzenesulfonate1-amino-2,6-dimethyl-quinolinium; 
• 2243-89-2 2,4,6-trimethylquinoline 
• 82105-00-8 4,9-Dimethyl-11-thia-8-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene 11-oxide 
• 22989-38-4 2-(Chloromethyl)-6-methylquinoline 
• 202262-63-3 6-(Chloromethyl)-2-methylquinoline 
• 168083-29-2 3-(6-methyl-2-quinolinylmethoxy)aniline 
• 67866-66-4 2-(4-methoxy-styryl)-6-methyl-quinoline 

Relevant academic research and scientific papers

1H, 13C and 15N NMR and GIAO CPHF calculations on two quinoacridinium salts

The complete 1H, 13C and 15N NMR assignments of two closely related quinoacridinium salts, 8,13-diethyl-6-methyl-8H-quino[4,3,2-kl]acridinium iodide and, 8,13-diethyl-3,6,11-trimethyl-8H-quino[4,3,2-kl]acridinium iodide, are described. The multinuclear 1D NMR and 2D shift-correlated NMR techniques HMQC, HSQC and HMBC were applied, accompanied by ab initia GIAO CPHF calculations of shielding constants. Copyright

Oxidation of 1,2-dihydroquinolines under mild and heterogeneous conditions

A combination of NaHSO4.H2O and Na2Cr2O7.2H2O in the presence of wet SiO2 were used as an effective oxidizing agent for the oxidation of 1,2-dihydroquinolines to their corresponding quinoline derivatives in dichloromethane at room temperature with excellent yields.

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies

We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.

ZnMe2-Mediated, Direct Alkylation of Electron-Deficient N-Heteroarenes with 1,1-Diborylalkanes: Scope and Mechanism

The regioselective, direct alkylation of electron-deficient N-heteroarenes is, in principle, a powerful and efficient way of accessing alkylated N-heteroarenes that are important core structures of many biologically active compounds and pharmaceutical agents. Herein, we report a ZnMe2-promoted, direct C2- or C4-selective primary and secondary alkylation of pyridines and quinolines using 1,1-diborylalkanes as alkylation sources. While substituted pyridines and quinolines exclusively afford C2-alkylated products, simple pyridine delivers C4-alkylated pyridine with excellent regioselectivity. The reaction scope is remarkably broad, and a range of C2- or C4-alkylated electron-deficient N-heteroarenes are obtained in good yields. Experimental and computational mechanistic studies imply that ZnMe2 serves not only as an activator of 1,1-diborylalkanes to generate (α-borylalkyl)methylalkoxy zincate, which acts as a Lewis acid to bind to the nitrogen atom of the heterocycles and controls the regioselectivity, but also as an oxidant for rearomatizing the dihydro-N-heteroarene intermediates to release the product.

Method for producing quinoline derivative through one-pot two-step method

The invention relates to a method for producing a quinoline derivative through a one-pot two-step method. According to the method, an aromatic nitro compound and fatty alcohol are used as raw materials, oxygen-containing molybdenum disulfide is used as a catalyst, firstly, under the conditions of 0.3-3.0-MPa hydrogen and 120-160 DEG C, a reaction is carried out for 2-10 h, the aromatic nitro compound is translated into an aromatic amine, then a reaction atmosphere is displaced, in an inert atmosphere or an oxygen-containing atmosphere, a reaction is carried out under the condition of 120-200 DEG C for 2-12 h, after the reaction is completed, a liquid-phase component is separated out, and is concentrated, and an obtained product is separated by a silica gel column to obtain a substituted qunoline compound. The synthesis method can have important application on the aspect of synthesis of quinoline compounds.

Method for preparing quinoline compound through oxidation and reduction integration (by machine translation)

The method takes the aromatic nitro compound and the fatty alcohol as. the raw material and uses the aromatic nitro compound and the fatty, alcohol as the catalyst to, react under an inert atmosphere or under the, 150-200 °C atmosphere containing oxygen 2-12h, at the atmosphere, of oxygen containing, oxygen, to obtain the substituted, quinoline compound, and. the synthesis method can have important application in the aspect of quinoline compound. synthesis. (by machine translation)

Half-Sandwich Ruthenium Complexes for One-Pot Synthesis of Quinolines and Tetrahydroquinolines: Diverse Catalytic Activity in the Coupled Cyclization and Hydrogenation Process

Four types of half-sandwich ruthenium complexes with an N,O-coordinate mode based on hydroxyindanone-imine ligands have been prepared in good yields. These stable ruthenium complexes exhibited high activity in the catalytic synthesis of quinolines from the reactions of amino alcohols with different types of ketones or secondary alcohols under very mild conditions. Moreover, the methodology for the direct one-pot synthesis of tetrahydroquinoline derivatives from amino alcohols and ketones has been also developed on the basis of the continuous catalytic activity of this ruthenium catalyst in the selective hydrogenation of the obtained quinoline derivatives with a low catalyst loading. The corresponding products, quinolines and tetrahydroquinoline derivatives, were afforded in good to excellent yields. The efficient and diverse catalytic activity of these ruthenium complexes suggested their potential large-scale application. All of the ruthenium complexes were characterized by various spectroscopies to confirm their structures.

Method for preparing quinoline derivative

The invention relates to a method for preparing a quinoline derivative. The method comprises the following steps: by taking aromatic amine compounds and fatty alcohol as raw materials and oxygen-containing molybdenum disulfide as a catalyst, performing a reaction for 2-12 hours in an inert atmosphere or an oxygen-containing atmosphere at the temperature of 120-200 DEG C, after the reaction is finished, separating liquid phase components, performing concentration, and performing separation through a silica gel column, so as to obtain a substituted quinoline compound. The synthetic method may have important application in the aspect of quinoline compound synthesis.

Potassium tert-Butoxide-Promoted Acceptorless Dehydrogenation of N-Heterocycles

Potassium tert-butoxide-promoted acceptorless dehydrogenation of N-heterocycles was efficiently realized for the generation of N-heteroarenes and hydrogen gas under transition-metal-free conditions. In the presence of KOtBu base, a variety of six- and five-membered N-heterocyclic compounds efficiently underwent acceptorless dehydrogenation to afford the corresponding N-heteroarenes and H2 gas in o-xylene at 140 °C. The present protocol provides a convenient route to aromatic nitrogen-containing compounds and H2 gas. (Figure presented.).