162784-88-5

Basic information

• Product Name: 1,8(2H,5H)-Acridinedione, 3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-(2-nitrophenyl)-
• CAS NO: 162784-88-5
• Molecular Formula: C23H26N2O4
• Molecular Weight: 394.47
• Mol File: 162784-88-5.mol

Chemical Properties

• CAS DataBase Reference: 1,8(2H,5H)-Acridinedione, 3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-(2-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8(2H,5H)-Acridinedione, 3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-(2-nitrophenyl)-(162784-88-5)
• EPA Substance Registry System: 1,8(2H,5H)-Acridinedione, 3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-(2-nitrophenyl)-(162784-88-5)

Safety Data

• Hazardous Substances Data: 162784-88-5(Hazardous Substances Data)

Usage

Potency

Potent fluorescence quencher

Applications

Used in biological and analytical applications

Photochemotherapeutic properties

Studied for potential use in cancer therapy

Antimicrobial and antifungal activities

Investigated for its potential in these areas

Versatility

Multifunctional chemical compound with potential applications in various fields

Upstream product

• 126-81-8 dimedone 
• 552-89-6 2-nitro-benzaldehyde 
• 30038-64-3 3,3,6,6-tetramethyl-9-(2-nitrophenyl)-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione 
• 612-25-9 2-Nitrobenzyl alcohol 
• 99-61-6 3-nitro-benzaldehyde 
• 873-95-0 1-amino-5,5-dimethylcyclohexen-3-one 
• 183737-77-1 2,2'-((2-nitrophenyl)methylene)bis(5,5-dimethylcyclohexane-1,3-dione) 

Relevant articles and documents

Facile and simple route to the synthesis of condensed acridine systems

Condensation of cyclohexane-1,3-dione or dimedone with o-nitrobenzaldehyde and ammonium acetate/acetic anhydride furnished the corresponding acridinedione/xanthene derivatives. The middle ring aromatization followed by reductive cyclization afforded the r

Efficient synthesis of decahydroacridine-1,8-diones and polyhydroquinolines using the step-wise method

Various symmetrical and unsymmetrical decahydroacridine-1,8-dione and polyhydroquinoline derivatives were synthesized via two-step cyclocondensation reactions. The advantages of this step-wise addition of reactants in comparison with other one-pot reactions are avoiding the formation of 2 or 3 undesired by-products, therefore allowing cleaner work up of reaction. The important factor of this effective cyclocondensation method is that the prepared β-enaminone component was added dropwise to the solution, in which the Knoevenagel condensation product is slowly being formed by reaction of aldehyde molecule and 1,3-dicarbonyl compounds. The results of the proposed step-wise method are compared and discussed with those obtained in the one-pot reactions.

An Efficient One-Pot Four-Component Synthesis of 9-Aryl-Hexahydroacridine-1,8-Dione Derivatives in the Presence of a Molecular Sieves Supported Iron Catalyst

Abstract: A series of 9-aryl-hexahydroacridine-1,8-diones are synthetized with good to excellent yields (50–99%) via a one-pot four-component reaction of dimedone, aromatic aldehydes and ammonium acetate in the presence of 4?? molecular sieves modified wi

Eco-friendly, ultrasound-assisted, and facile synthesis of one-pot multicomponent reaction of acridine-1,8(2H,5H)-diones in an aqueous solvent

A one-pot, multistep synthesis of acridine-1,8(2H,5H)-diones (4a–m) was achieved by three-component reaction of dimedone (1) with an aromatic aldehyde (2a–m) and an ammonium acetate (3) using water as a green solvent without any catalyst and a simple, eas

N-Propyl benzoguanamine sulfonic acid supported on magnetic Fe3O4 nanoparticles: A novel and efficient magnetically heterogeneous catalyst for the synthesis of 1,8-dioxo-decahydroacridine derivatives

In this study, N-propyl-benzoguanamine-SO3H-stabilized magnetic nanoparticles were prepared as a new heterogeneous acid catalyst in accordance with the principles of green chemistry. The new catalyst is used for the synthesis of derivatives of

Catalytic application of sulfonic acid-functionalized titana-coated magnetic nanoparticles for the preparation of 1,8-dioxodecahydroacridines and 2,4,6-triarylpyridines via anomeric-based oxidation

We have developed green, efficient and powerful protocols for the preparation of 2,4,6-triarylpyridines and 1,8-dioxodecahydroacridines in the presence of Fe3O4@TiO2@O2PO2(CH2)2NHSO3H as a sulfonic acid-functionalized titana-coated magnetic nanoparticle catalyst under mild and solvent-free reaction conditions. These protocols furnished the desired products in short reaction times with good to high yields (20–40?min and 80–86% in the case of 2,4,6-triarylpyridines; 15–90?min and 80–93% in the case of 1,8-dioxodecahydroacridines). The final step of the mechanistic route in the synthesis of 2,4,6-triarylpyridines proceeds via an anomeric-based oxidation. Also, the nanomagnetic core–shell catalyst can be recycled and reused in both cases of the scrutinized one-pot multicomponent reactions with high turnover number and turnover frequency.

Hollow Fe3O4@DA-SO3H: an efficient and reusable heterogeneous nano-magnetic acid catalyst for synthesis of dihydropyridine and dioxodecahydroacridine derivatives

Abstract: In this work, for the first time, a highly stable and efficient super-paramagnetic catalyst, H-Fe3O4@DA-SO3H, involving hollow morphology of Fe3O4 as core and dopamine as shell was prepared

Choline chloride catalyzed eco-friend and effective one-pot synthesis of 9-arylacridine-1,8-dione and hexahydroquinoline via Hantzsch type reaction

Choline chloride was utilized to efficiently catalyzed Hantzsch type reaction for the synthesis of 9-arylacridine-1,8-dione and hexahydroquinoline derivatives. The optimized catalytic system benefits from facile operation and separation procedures, in goo

Green and efficient synthesis of acridine-1,8-diones and hexahydroquinolines via a KH2PO4 catalyzed Hantzsch-type reaction in aqueous ethanol

Abstract: A simple, clean, and economical methodology for the synthesis of acridine-1,8-dione and hexahydroquinoline derivatives via Hantzsch-type condensation has been described. This study highlights the development of a new green pathway for the prepar

Benzyl alcohol-based synthesis of mono- and bis-dihydropyridines in the presence of Al(HSO4)3, sodium nitrite, and sodium bromide under solvent-free conditions

Dihydropyridines were synthesized in good to excellent yields in the presence of NaNO2, Al(HSO4)3, and a catalytic amount of NaBr at room temperature. Low cost, the use of available reagents, simple methodology, and easy work-up procedure make this method attractive for organic synthesis.