49545-70-2

Usage

Molecular Structure

2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one consists of a complex structure that includes a chlorobenzylidene group (a benzylidene group with a chlorine atom attached to the benzene ring) and a dihydronaphthalenone group (a naphthalenone group with two additional carbon atoms forming a six-membered ring).

Common Uses

This chemical compound is commonly used in the synthesis of pharmaceuticals and agrochemicals.

Potential Applications

2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one has potential applications as an intermediate for the production of various drugs and agricultural chemicals.

Chemical Reactivity

The compound has a versatile chemical structure and reactivity, making it useful in the synthesis of various products.

Safety Precautions

It is important to handle and use 2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one with caution due to its potential for toxic and hazardous properties.

Further Research

More research and development is needed to explore the potential uses and applications of 2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one in various industries.

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 873-76-7 para-Chlorobenzyl alcohol 

Downstream Products

• 129116-55-8 1-(4-Chloro-phenyl)-3-oxo-1,2,3,9,10,10a-hexahydro-phenanthrene-2-carboxylic acid (2-chloro-phenyl)-amide 
• 129078-78-0 1-(4-Chloro-phenyl)-3-oxo-1,2,3,9,10,10a-hexahydro-phenanthrene-2-carboxylic acid (2-nitro-phenyl)-amide 
• 129116-56-9 1-(4-Chloro-phenyl)-3-oxo-1,2,3,9,10,10a-hexahydro-phenanthrene-2-carboxylic acid (4-dimethylamino-phenyl)-amide 
• 128483-26-1 2-Mercapto-4-p-chlorophenyl-4H-1,2,3,4,5,6-hexahydrobenzo-quinazoline 
• 78364-68-8 2-Bromo-2-[bromo-(4-chloro-phenyl)-methyl]-3,4-dihydro-2H-naphthalen-1-one 
• 612087-56-6 2-(4-chloro-benzyl)-1,2,3,4-tetrahydro-[1]naphthol 
• 933467-66-4 7-(4-chlorophenyl)-10-thioxo-5,6,10,11-tetrahydro-9H-benzo[h]pyrimido[4,5-b]quinolin-8-one 
• 1187455-89-5 4-(4-chloro-phenyl)-2-(4-pyridin-2-yl-piperazin-1-yl)-5,6-dihydro-benzo[h]quinazoline 
• 1187456-06-9 C₂₇H₂₆ClN₅ 
• 1187456-05-8 C₂₂H₂₂ClN₃ 
• 1187455-88-4 C₂₂H₂₀ClN₃ 
• 1187455-86-2 C₂₂H₂₀ClN₃O 
• 1187456-03-6 4-(4-chloro-phenyl)-2-morpholin-4-yl-3,4,5,6-tetrahydro-benzo[h]quinazoline 
• 1187455-87-3 4-(4-chlorophenyl)-2-piperidin-1-yl-5,6-dihydro-benzo[h]quinazoline 

Relevant academic research and scientific papers

Asymmetric Transfer Hydrogenation of Arylidene-Substituted Chromanones and Tetralones Catalyzed by Noyori-Ikariya Ru(II) Complexes: One-Pot Reduction of C═C and C═O bonds

3-Arylidenechroman-4-ones and 2-arylidene-1-tetralones are hydrogenated to cis-benzylic alcohols in dr's and er's up to 99:1 via a C═C and C═O one-pot reduction in the presence of 2-5 mol % Noyori-Ikariya-type RuII chiral complexes and HCO2Na as a hydroge

Tetralone derivatives are MIF tautomerase inhibitors and attenuate macrophage activation and amplify the hypothermic response in endotoxemic mice

Macrophage migration inhibitory factor (MIF) is a pro-inflammatory cytokine playing crucial role in immunity. MIF exerts a unique tautomerase enzymatic activity that has relevance concerning its multiple functions and its small molecule inhibitors have been proven to block its pro-inflammatory effects. Here we demonstrate that some of the E-2-arylmethylene-1-tetralones and their heteroanalogues efficiently bind to MIF’s active site and inhibit MIF tautomeric (enolase, ketolase activity) functions. A small set of the synthesised derivatives, namely compounds (4), (23), (24), (26) and (32), reduced inflammatory macrophage activation. Two of the selected compounds (24) and (26), however, markedly inhibited ROS and nitrite production, NF-κB activation, TNF-α, IL-6 and CCL-2 cytokine expression. Pre-treatment of mice with compound (24) exaggerated the hypothermic response to high dose of bacterial endotoxin. Our experiments suggest that tetralones and their derivatives inhibit MIF’s tautomeric functions and regulate macrophage activation and thermal changes in severe forms of systemic inflammation.

I2/TBHP mediated diastereoselective synthesis of spiroaziridines

Eventhough spiroheterocycles are considered as emerging drug candidates, synthesis of spiroaziridines has not been well explored so far. Herein, we disclose an efficient I2/TBHP mediated diastereoselective synthesis of N-alkyl spiroaziridines from primary amines and easily accessible α,β-unsaturated ketones. The reaction is also compatible for the synthesis of 2-aroylaziridines.

Ash of pomegranate peels (APP): A bio-waste heterogeneous catalyst for sustainable synthesis of α,α′-bis(substituted benzylidine)cycloalkanones and 2-arylidene-1-tetralones

Abstract: α,α′-bis(substituted benzylidene)cycloalkanones were efficiently prepared from variously substituted aldehydes and cycloalkanones in water by using ash of pomegranate peels (APP) as a catalyst. The APP-catalyst was obtained from bio-waste by simple thermal treatment to dry peels of pomegranate fruit and formation of its active phase was confirmed by FT-IR, XRD, XRF, EDX, SEM, DSC-TGA and BET techniques. The analysis revealed that the present catalyst has basic sites which promote the synthesis of desired products. The main attractions of our protocol are utilization of highly abundant bio-waste-derived catalyst and good-to-excellent yield in shortest reaction time. This green protocol was further extended for structurally diverse 2-arylidene-1-tetralones by condensation of equimolar quantity of aromatic aldehydes and 1-tetralone at low temperature. The catalyst could be quantitatively recovered and reused effectively for five times. Graphic abstract: [Figure not available: see fulltext.].

A simple iron-catalyst for alkenylation of ketones using primary alcohols

Herein, we developed a simple iron-catalyzed system for the α-alkenylation of ketones using primary alcohols. Such acceptor-less dehydrogenative coupling (ADC) of alcohols resulted in the synthesis of a series of important α,β-unsaturated functionalized ketones, having aryl, heteroaryl, alkyl, nitro, nitrile and trifluoro-methyl, as well as halogen moieties, with excellent yields and selectivity. Initial mechanistic studies, including deuterium labeling experiments, determination of rate and order of the reaction, and quantitative determination of H2 gas, were performed. The overall transformations produce water and dihydrogen as byproducts.

Novel 1-tetralone chalcone and composition for preventing or treating inflammatory disease comprising the same as active ingredient

Novel 1 -tetralone chalcone derivatives, 1-tetralone alone alone alone alone. A composition containing 6 - amino -1 - tetralone chalcone derivatives and 6-amino-1-tetralone alone alone alone alone is provided to systematically design 32 halogenated 1 -tet

Basic Anion-Exchange Resin-Catalyzed Aldol Condensation of Aromatic Ketones with Aldehydes in Continuous Flow

A general method for the aldol condensation of aromatic ketones with aldehydes was developed under continuous-flow conditions using a commercially available, strongly basic anion-exchange resin (A26) as catalyst. This procedure, in addition to exhibiting a wide substrate scope, promoted carbon-carbon bond formation under mild conditions using a quasi-stoichiometric ratio of starting reagents with good to excellent yields, thereby forming a limited amount of waste and allowing the process to be applied to sequential-flow systems. A proof of concept was developed in the first fully heterogeneously catalyzed two-step flow synthesis of donepezil, which is a blockbuster commercial anti-Alzheimer's drug.

Introduction of amino moiety enhances the inhibitory potency of 1-tetralone chalcone derivatives against LPS-stimulated reactive oxygen species production in RAW 264.7 macrophages

The design and synthesis of a series of thirty-two halogenated 1-tetralone or 6-amino-1-tetralone chalcone derivatives was achieved by the Claisen-Schmidt condensation reaction and were evaluated for their inhibitory effects against ROS production in LPS-stimulated RAW 264.7 macrophages. It was observed that the introduction of amino moiety into 1-tetralone skeleton greatly increased the inhibitory potency compared to corresponding 1-tetralone chalcones. Among the synthesized compounds, compound 18 which consists of 6-amino-1-tetralone skeleton together with o-fluorobenzylidene showed the most potent ROS inhibitory effect with IC50 value of 0.25 ± 0.13 μM. SAR analysis revealed that amino moiety at the 6th position of 1-tetralone chalcones have an important role for exerting the greater ROS inhibitory potency in LPS-stimulated RAW 264.7 macrophages than those exhibited by 1-tetralone chalcones alone.

Base-mediated one-pot synthesis of 3,4,5,6-tetrahydro-4-substituted benzo[h]quinazoline-2(1H)-thione derivatives and evaluation of their antioxidant activity

One-pot three-component Beginelli-like reactions of a ketone 1, an aryl aldehyde 2, and thiourea 3 in the presence of sodium hydroxide are described. In this reaction, 3,4,5,6-tertrahydro-4-substituted quinazoline-2(1H)-thione derivatives 4a–h were obtain

Selectivity in the Aerobic Dearomatization of Phenols: Total Synthesis of Dehydronornuciferine by Chemo- and Regioselective Oxidation

We describe a selective aerobic oxidation of meta-biaryl phenols that enables rapid access to functionalized phenanthrenes. Aerobic oxidations attract interest due to their efficiency, but remain underutilized in complex molecule settings due to challenge