59082-26-7

Basic information

• Product Name: 2-(4-methylbenzylidene)-3,4-dihydro-1(2H)-naphthalenone
• Synonyms: 2-(4-methylbenzylidene)-3,4-dihydro-1(2H)-naphthalenone
• CAS NO: 59082-26-7
• Molecular Formula: C₁₈H₁₆O
• Molecular Weight: 248.31904
• Mol File: 59082-26-7.mol

Chemical Properties

• Boiling Point: 413.3°C at 760 mmHg
• Flash Point: 181.9°C
• Appearance: /
• Density: 1.145g/cm³
• Vapor Pressure: 4.84E-07mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: 2-(4-methylbenzylidene)-3,4-dihydro-1(2H)-naphthalenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methylbenzylidene)-3,4-dihydro-1(2H)-naphthalenone(59082-26-7)
• EPA Substance Registry System: 2-(4-methylbenzylidene)-3,4-dihydro-1(2H)-naphthalenone(59082-26-7)

Safety Data

• Hazardous Substances Data: 59082-26-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H16O/c1-13-6-8-14(9-7-13)12-16-11-10-15-4-2-3-5-17(15)18(16)19/h2-9,12H,10-11H2,1H3/b16-12+

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 

Downstream Products

• 78364-66-6 2-Bromo-2-(bromo-p-tolyl-methyl)-3,4-dihydro-2H-naphthalen-1-one 
• 157282-76-3 7-p-Tolyl-5,7-dihydro-6H-10-thia-7a,11-diaza-cyclopenta[b]phenanthren-8-one 
• 157282-85-4 7-p-Tolyl-9-[1-p-tolyl-meth-(E)-ylidene]-5,7-dihydro-6H-10-thia-7a,11-diaza-cyclopenta[b]phenanthren-8-one 
• 157282-87-6 9-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-7-p-tolyl-5,7-dihydro-6H-10-thia-7a,11-diaza-cyclopenta[b]phenanthren-8-one 
• 1227624-17-0 8-methoxy-3-(1-(4-methylphenyl)-9,10-dihydro-4-azaphenanthren-3-yl)coumarin 
• 1227624-12-5 3-[1-(4-methylphenyl)-9,10-dihydro-4-azaphenanthren-3-yl]coumarin 
• 1227624-22-7 2-[1-(4-methylphenyl)-9,10-dihydro-4-azaphenanthren-3-yl]benzo[f]coumarin 
• 1379762-78-3 (2R,3'S)-3'-(4-methphenyl)-3,4-dihydro-1H-spiro[naphthalene-2,2'-oxiran]-1-one 
• 97145-60-3 4-(p-tolyl)-5,6-dihydrobenzo[h]quinazolin-2-amine 
• 106368-06-3 3-p-Tolyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole 
• 109329-43-3 3-Phenyl-4-p-tolyl-3,4,5,6-tetrahydro-1H-benzo[h]quinolin-2-one 
• 83388-32-3 3-Phenyl-4-p-tolyl-5,6-dihydro-benzo[h]quinoline 

Relevant articles and documents

A class of 2-benzylene tetrahydronaphthalone derivatives and preparation methods and applications thereof

The present invention relates to the field of biotechnology, discloses a class of 2-benzylene tetrahydrophthalone derivatives and preparation methods and applications thereof. 2-Benzylene tetrahydronaphthalone derivative having the following structural formula, wherein R1 is selected from chlorine, bromine, iodine, alkyl, alkoxy, substituted or unsubstituted amino, alkylthio, alkyneoxy, hydroxy or hydroxymethyl group; R2, R3, R4 are hydrogen or carboxyl-containing substituents, and R2, R3, or R4 At least one of them is a carboxyl-containing substituent group. The present invention innovatively proposes a class of 2-benzylene tetrahydronaphthalone derivatives as a new skeleton of firefly luciferase inhibitors. A class of 2-benzylene tetrahydronaphthone derivatives of the present invention having a highly efficient inhibitor of nanomolar and a nanamol IC50; by competing with D- fluorescein reversibly inhibits firefly luciferase, and exhibits a high effect of firefly glowworm luciferase inhibition at the enzyme, intracellular and in vivo levels; at the same time, it is shown that it has good biocompatibility and application potential.

Copper/GanPhos-Catalyzed 1,3-Dipolar Cycloaddition of Azo?-methine Ylides: An Efficient Access to Chiral Pyrrolidine Spirocycles

A highly efficient copper/GanPhos-catalyzed 1,3-dipolar cyclo?-addition?-of azomethine ylides is reported. This viable transformation provides a series of optically active spiro[dihydronaphthalene-2,3′-pyrrolidine]s, bearing one spiro quaternary and three tertiary stereogenic centers, in good yields and with high ee values. This protocol features high diastereo- A nd enantioselectivity, broad substrate scope and mild reaction conditions.

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.

Claisen-Schmidt, aza-Michael, cyclization via cascade strategy toward microwave promoted synthesis of imidazo[2,1-b]quinazolines

Imidazole blended quinazolines are having a wide run of potential applications in synthetic field. In this current investigation, we reported a modern synthesis with the help of non-conventional energy. Optimization parameters have been stabilized utilizi

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.

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

Synthesis, characterization, and investigations of antimicrobial activity of 6,6-dimethyl-3-aryl-3′,4′,6,7-tetrahydro-1′H,3H-spiro[benzofuran-2,2′-naphthalene]-1′,4(5H)-dione

Chalcone-like compounds 3a–l, 2-(benzylidene)-3,4-dihydronaphthalen-1(2H)-one, were synthesized from the addition of different benzaldehyde derivatives (2a–l) to 1,2,3,4-tetrahydro-1-napthalone (1) in basic medium. Mn(OAc)3-mediated addition of

Antibacterial and antitubercular evaluation of dihydronaphthalenone-indole hybrid analogs

A new series of indole appended dihydronaphthalenone hybrid analogs (5a–t) have been synthesized through the Lewis acid catalyzed Michael addition of indoles to the arylidene/hetero arylidene ketones. All the synthesized derivatives are well characterized

BF3·Et2O mediated one-step synthesis of N-substituted-1,2-dihydropyridines, indenopyridines and 5,6-dihydroisoquinolines

A simple and efficient one-pot synthesis of N-substituted-1,2-dihydropyridines, indenopyridines and 5,6-dihydroisoquinolines by a BF3·Et2O mediated novel methodology, from easily available α,β-unsaturated ketones/arylidene ketones, phenyl acetylenes and substituted nitriles, has been described. This novel annulation provides quick access to complex polycyclic frameworks with an excellent substrate scope.