10265-82-4

Basic information

• Product Name: 1H-Cyclopenta[b]quinoline, 2,3-dihydro-9-phenyl-
• CAS NO: 10265-82-4
• Molecular Formula: C18H15N
• Molecular Weight: 245.324
• Mol File: 10265-82-4.mol
• Article Data: 79

Chemical Properties

• CAS DataBase Reference: 1H-Cyclopenta[b]quinoline, 2,3-dihydro-9-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Cyclopenta[b]quinoline, 2,3-dihydro-9-phenyl-(10265-82-4)
• EPA Substance Registry System: 1H-Cyclopenta[b]quinoline, 2,3-dihydro-9-phenyl-(10265-82-4)

Safety Data

• Hazardous Substances Data: 10265-82-4(Hazardous Substances Data)

Usage

Polycyclic aromatic hydrocarbon

It is a type of hydrocarbon with multiple aromatic rings in its structure.

Cyclopentane ring

A five-carbon ring structure, which is part of the compound's core structure.

Quinoline ring

A tricyclic aromatic compound consisting of a benzene ring fused to a pyridine ring, also part of the compound's core structure.

Phenyl group

A benzene ring with a single bond to an atom or group, in this case, attached to the 9th position of the compound.

Potential biological activity

The compound may have effects on biological systems, making it of interest in medicinal chemistry and pharmaceutical research.

Antitumor potential

The compound has been studied for its potential to inhibit the growth of tumors, making it a candidate for cancer treatment research.

Inhibitory effects on enzymes

The compound may have the ability to interfere with the function of certain enzymes, which could be useful in the development of new drugs.

Applications in synthesis of organic compounds

The compound may serve as a building block or intermediate in the synthesis of other organic compounds, contributing to the development of new chemical products.

Development of new materials

The compound's unique structure and properties may contribute to the creation of new materials with potential applications in various industries.

Upstream product

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• 120-92-3 cyclopentanone 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 536-74-3 phenylacetylene 
• 1001593-46-9 2-diphenylmethylenecyclopentanone O-methyloxime 
• 96-41-3 Cyclopentanol 
• 136954-19-3 1,6-diphenyl-hex-5-yn-1-one 
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• 856120-87-1 (6-azidohex-1-yn-1-yl)benzene 
• 14918-21-9 5-hexynonitrile 
• 591-50-4 iodobenzene 

Relevant articles and documents

CuO nanoparticles as an efficient and reusable catalyst for the one-pot friedlander quinoline synthesis

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Efficient Friedlaender synthesis of quinoline derivatives from 2-aminoarylketones and carbonyl compounds mediated by recyclable PEG-supported sulfonic acid

2-Aminoarylketones undergo smooth condensation with α-methylene ketones in the presence of 10 mol% of poly(ethylene glycol) (PEG)-supported sulfonic acid under mild reaction conditions to afford the corresponding poly-substituted quinolines in excellent y

Dowex-50w promoted friedlaender synthesis of substituted quinolines under solvent-free conditions

An efficient method for the synthesis of substituted quinolines using Dowex-50W ion exchange resin as reusable eco-friendly catalyst vai Friedlaender annulation under solvent-free conditions is described. The Japan Institute of Heterocyclic Chemistry.

Palladium-Catalyzed Regioselective Oxidative Annulation of Cyclohexanones and 2-Aminophenyl Ketones Using Molecular Oxygen as the Sole Oxidant

A facile oxidative annulation of cyclohexanones and 2-aminophenyl ketones that uses molecular oxygen as the sole oxidant is described. The reaction provides a direct approach to acridines, a structural motif for a large number of fluorescent sensors, functional materials, ligands, and pharmaceuticals. In the presence of a palladium catalyst, high regioselectivity is observed when using non-symmetric 3-substituted cyclohexanones. With the use of oxygen as the terminal redox moderator, the electron gap of the global redox condensation process is filled and the reaction efficiency is significantly promoted. This protocol possesses many advantages such as using non-hazardous oxidant and readily available starting materials, high regioselectivity, and water as the only by-product. (Figure presented.).

Gd(OTf)3-[Bmim][PF6]: A novel and recyclable catalytic system for the synthesis of quinolines

A mild and efficient route for the synthesis of quinolines and polycyclic quinolines utilizing Gadolinium triflate (Gd(OTf)3) as a novel catalyst via Friedlaender annulation in ionic liquid 1-n-butyl-3- methylimidazolium hexafluorophosphate [Bm

Friedlaender quinoline synthesis catalyzed by M(HSO4) n (M=Al, Mg, Ca) under solvent-free conditions

Polysubstituted quinolines were synthesized from the 2-aminobenzophenone, ethylacetoacetate or ketones in the presence of metal hydrogen sulfates [M(HSO4)n] in good to high yields at 70 °C under solvent-free conditions. The Japan Ins

3-Methyl-1-sulfoimidazolium ionic liquids as recyclable medium for efficient synthesis of quinoline derivatives by Friedl?nder annulation

Two acidic ionic liquids, 3-methyl-1-sulfoimidazolium trichloroacetate ([Msim][OOCCCl3]) and 3-methyl-1-sulfoimidazolium chloride ([Msim]Cl) were efficiently utilized as recyclable acidic homogeneous medium for the Friedl?nder synthesis of quin

An efficient protocol for the Friedlaender quinoline synthesis using the Lewis acidic ionic liquid choline chloride · 2ZnCl2

Lewis acidic ionic liquid choline chloride · 2ZnCl2 is shown to be for the first time an excellent solvent and efficient catalyst for the synthesis of quinolines via Friedlaender annulation under mild conditions.

Magnetite (Fe3O4) nanoparticles-supported dodecylbenzenesulfonic acid as a highly efficient and green heterogeneous catalyst for the synthesis of substituted quinolines and 1-amidoalkyl-2-naphthol derivatives

Abstract: Magnetically retrievable, magnetite (Fe3O4) nanoparticles-supported dodecylbenzenesulfonic acid (DDBSA@MNP) was synthesized and characterized through different analytical techniques such as TEM, XRD, FTIR, TGA, SEM, EDX and

Versatile Barium and Calcium Imidazolium-Dicarboxylate Heterogeneous Catalysts in Quinoline Synthesis

This article details the development of heterogeneous catalysts based on calcium and barium in combination with the organic linker 1,3-bis(carboxymethyl)imidazolium (bcmim). The linker and the materials from alkaline earth metals are easily prepared under very smooth conditions. The use of linkers with different counterions (Cl or Br) provided different materials. Calcium- and barium-based catalysts were successfully employed in the preparation of quinoline derivatives from ketones and 2-aminoarylaldehydes or 2-aminoarylketones. In general, barium-based catalysts provided better results than calcium, although the latter are an excellent complement for certain substrates. Thus, a notable feature of such catalysts is the possibility of accessing a variety of complementary heterogeneous catalytic systems, rendering the catalysis adaptive to the reactant.||||||.

Homogeneous catalysis, heterogeneous recycling: A new family of branched molecules with hydrocarbon or fluorocarbon chains for the Friedl?nder synthesis of quinoline under solvent-free conditions

A new family of branched catalysts with hydrocarbon or fluorocarbon chains was used to catalyze Friedl?nder reaction between 2-aminoarylketones and α-methylene ketones under solvent-free conditions in good to excellent yields. The catalysts exhibit temperature-dependent solubility and such a thermomorphic character allows them to be recovered by filtration conveniently at room temperature and reused at least five times. To some extent, the branched catalysts with hydrocarbon chains are superior to those with fluorocarbon chains, as they are cheaper and more biodegradable.

Molecular iodine: A highly efficient catalyst in the synthesis of quinolines via Friedlaender annulation

A mild and efficient route for the synthesis of quinolines and polycyclic quinolines via Friedlaender annulation, utilizing molecular iodine (1 mol%) as a new catalyst, is described. The Royal Society of Chemistry 2006.

An improved quinoline synthesis in the presence of nickel chloride

NiCl2·6H2O has been used as an efficient catalyst for the synthesis of quinolines by the reaction of 2-aminoaryl ketones and (α-methyleneketones under the solvent-free conditions. The clean, mild acidity conditions and quantitative y

A green biosynthesis of NiO nanoparticles using aqueous extract of Tamarix serotina and their characterization and application

Nickel oxide nanoparticles were prepared using nickel nitrate as precursor with extract of Tamarix serotina flowers and were characterized using powder X-ray diffraction, infrared and UV spectroscopies, transmission electron microscopy, vibrating sample m

Microwave-assisted solvent-free synthesis of quinolines using N-bromosulfonamides

Quinolines were readily prepared under new convenient conditions using poly(N,N'-dibromo-N,N'-dimethylenebenzene-1,3-disulfonamide) (PBBS) or N,N,N',N'-tetra bromo benzene-1,3-disulfonamide (TBBDA) as efficient reagents from 2-aminobenzophenones and keton

Introduction of a novel Br?nsted acidic ionic liquid for the promotion of the synthesis of quinolines

3,3′-(Butane-1,4-diyl) bis (1-methyl-1H-imidazol-3-ium) ·dibromide·disulfuric acid (C4(mim)2- 2Br--2H2SO4) as a new ionic liquid was prepared and efficiently used for the promotion of the one-pot synt

Sustainable Synthesis of Quinolines and Pyrimidines Catalyzed by Manganese PNP Pincer Complexes

This study represents the first example an environmentally benign, sustainable, and practical synthesis of substituted quinolines and pyrimidines using combinations of 2-aminobenzyl alcohols and alcohols as well as benzamidine and two different alcohols,

Fast, solvent-free, microwave-promoted friedlaender annulation with a reusable solid catalyst

A fast, solvent-free method is described for the synthesis of substituted quinoline derivatives via Friedlander cyclization, employing a reusable solid catalyst (silica-propylsulfonic acid). Although it worked best under microwave irradiation (with generally more than 90% isolated yields in 30min), the reaction was also feasible under conventional heating (with fair to good yields in about 5h).

Oxalic acid: An efficient and cost-effective organic catalyst for the Friedlaender quinoline synthesis under solvent-free conditions

Oxalic acid is used as an efficient catalyst in the condensation of 2-aminoaryl ketones with carbonyl compounds leading to the formation of quinolines in excellent yields under solvent-free conditions. This methodology offers significant improvements for

A new green approach to the Friedl?nder synthesis of quinolines

A new approach to the Friedl?nder synthesis of quinolines is described. Polysubstituted quinolines are readily prepared under milder conditions than in other existing methods through a gold(III)-catalysed sequential condensation/annulation reaction of o-a

Imidazole-functionalized magnetic Fe3O4 nanoparticles: an efficient, green, recyclable catalyst for one-pot Friedl?nder quinoline synthesis

An efficient and cost-effective procedure for preparation of Fe3O4 nanoparticles and supported Br?nsted acidic ionic liquid 1-methyl-3-(3-trimethoxysilylpropyl)imidazolium hydrogen sulfate (Fe3O4-IL-HSO4/s

LiBr-catalyzed simple and efficient synthesis of some novel substituted quinolines via Friedlander heteroannulation reaction

A simple and efficient method has been developed for the condensation of o-aminoaryl ketones with α-methylene ketones in the presence of catalytic amounts of LiBr to afford the corresponding fused cyclic quinolines in high yield using the Friedlander hete

Poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) and N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide as efficient reagents for synthesis of quinolines

Poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) [PBBS] and N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide [TBBDA] were used as efficient reagents for the synthesis of quinolines in excellent yields from 2-aminoaryl ketones and carbonyl compounds under aqueo

A mild and efficient one-step synthesis of quinolines

2-Aminoaryl ketones undergo condensation with α-methylene ketones in the presence of a catalytic amount of Y(OTf)3 at room temperature under mild conditions to afford the corresponding polysubstituted quinolines in excellent yields.

Rapid and Efficient Microwave-Assisted Friedl?nder Quinoline Synthesis

A microwave-based methodology facilitates reaction of 2-aminophenylketones with cyclic ketones to form a quinoline scaffold. Syntheses of amido- and amino-linked 17β-hydroxysteroid dehydrogenase type 3 inhibitors with a benzophenone-linked motif were purs

Synthesis of neocryptolepines and carbocycle-fused quinolines and evaluation of their anticancer and antiplasmodial activities

This study reported the discovery of novel compounds containing five-membered ring fused quinoline core structures as anticancer and antimalarial agents. Two libraries containing these core structures, neocryptolepines and carbocycle-fused quinolines, were prepared and evaluated. Compound 3h was found to be much more potent than other analogs against cancer cell lines with high selectivity. Meanwhile, carbocycle-fused quinolines 5h and 5s showed moderate anticancer properties but much less cytotoxicity to normal cell than doxorubicin. In addition, compound 3h also showed much lower cytotoxic against human normal kidney cell line compared to doxorubicin standard. However, only compounds 3s and 3p provided acceptable results for antimalarial activities.