164410-73-5

Basic information

• Product Name: 2-amino-7,7-dimethyl-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• Synonyms: 2-amino-7,7-dimethyl-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile;2-amino-7,7-dimethyl-4-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• CAS NO: 164410-73-5
• Molecular Formula: C22H20N2O2
• Molecular Weight: 344.4064
• Mol File: 164410-73-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-amino-7,7-dimethyl-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-7,7-dimethyl-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile(164410-73-5)
• EPA Substance Registry System: 2-amino-7,7-dimethyl-4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile(164410-73-5)

Safety Data

• Hazardous Substances Data: 164410-73-5(Hazardous Substances Data)

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 66-77-3 1-naphthaldehyde 
• 109-77-3 malononitrile 
• 2972-83-0 (1-naphthylmethylidene)malononitrile 
• 126-81-8 dimedone 

Relevant articles and documents

2-Amino-4-(1-naphthyl)-5-oxo5,6,7,8-tetrahydro-4H-chromene3-carbonitrile and 2-amino-7,7-dimethyl-4-(1-naphthyl)-5-oxo-5,6,7, 8-tetrahydro-4H-chromene-3-carbonitrile

Syntheses and X-ray structural investigations have been carried out for the two title compounds, C20H16N2O 2, (IIIa), and C22H20N2O 2, (IIIb). In (IIIa), the heterocyclic ring adopts a sofa conformation, while in (IIIb), the ring has a flattened boat conformation. In both molecules, the fused cyclohexenone ring adopts a sofa conformation. The dihedral angles between these two flat fragments are 3.5 (2) and 17.5 (2)° in (IIIa) and (IIIb), respectively. The dihedral angles between the pseudo-axial naphthalene substituents and the planes of the pyran rings are 90. 9 (1) and 96.7 (1)°, respectively. In the crystal structure of (IIIa), intermolecular N-H...N and N-H...O hydrogen bonds link the molecules into infinite tapes along the b axis, while molecules of (IIIb) form centrosymmetric dimers via N-H...N hydrogen bonds, with only one H atom of the NH2 donor group taking part in hydrogen bonding.

One-pot synthesis of 2-amino-3-cyano-4H-pyrans and pyran-annulated heterocycles using sodium citrate as an organo-salt based catalyst in aqueous ethanol

Sodium citrate as a highly efficient catalyst is developed for the synthesis of functionalized 2-amino-3-cyano-4H-pyrans and pyran-annulated heterocycles. This method involves a one-pot three-component reaction of aromatic aldehydes, malononitrile and 1,3

Zn (II)-Schiff base covalently anchored to CaO@SiO2: A hybrid nanocatalyst for green synthesis of 4H-pyrans

In this study, the Zn (II)-Schiff base covalently anchored onto the surface of CaO@SiO2 nanoparticles. The structure of this hybrid nanomaterial (CaO@SiO2-NH2-Sal-Zn) was characterized using the analytical techniques such

Effect of Substituents on the Crystal Structures, Optical Properties, and Catalytic Activity of Homoleptic Zn(II) and Cd(II) β-oxodithioester Complexes

Five novel zinc(II) and cadmium(II) β-oxodithioester complexes, [Zn(L1)2] (1), [Zn(L2)2]n (2), [Zn(L3)2]n (3) [Cd(L1)2]n (4), [Cd(L2)2]n (5), with β-oxodithioester ligands, where L1 = 3-(methylthio)-1-(thiophen-2-yl)-3-thioxoprop-1-en-1-olate, L2 = 3-(methylthio)-1-(pyridin-3-yl)-3-thioxoprop-1-en-1-olate, and L3 = 3-(methylthio)-1-(pyridin-4-yl)-3-thioxoprop-1-en-1-olate, were synthesized and characterized by elemental analysis, IR, UV-vis, and NMR spectroscopy (1H and 13C{1H}). The solid-state structures of all complexes were ascertained by single-crystal X-ray crystallography. The β-oxodithioester ligands are bonded to Zn(II)/Cd(II) metal ions in an Oa§S and N chelating/chelating-bridging fashion leading to the formation of 1D (in 2-4) and 2D (in 5) coordination polymeric structures, but complex 1 was obtained as a discrete tetrahedral molecule. Complex 4 crystallizes in the C2 chiral space group and has been studied using circular dichroism (CD) spectroscopy. The multidimensional assemblies in these complexes are stabilized by many important noncovalent C-H···π(ZnOSC3, chelate), ?···?, C-H···?, and H···H interactions. The catalytic activities of 1-5 in reactions involving C-C and C-O bond formation have been studied, and the results indicated that complex 3 can be efficiently utilized as a heterogeneous bifunctional catalyst for the Knoevenagel condensation and multicomponent reactions to develop biologically important organic molecules. The luminescent properties of complexes were also studied. Interestingly, zinc complexes 1-3 showed strong lumniscent emission in the solid state, whereas cadmium complexes 4 and 5 exhibited bright luminescent emission in the solution phase. The semiconducting behavior of the complexes was studied by solid-state diffuse reflectance spectra (DRS), which showed optical band gaps in the range of 2.49-2.62 eV.

Horsetail plant (Equisetum arvense) and horsetail plant ash: application and comparison of their catalytic activities as novel and natural porous lewis acid catalysts for the one-pot green synthesis of 2-amino-4H-chromene derivatives under solvent-free co

This study aims to use a new medicinal porous plant having a high content of silica known as horsetail and horsetail ash for the first time as novel, efficient, and environmentally friendly natural mild catalysts. The structure of these catalysts was char

A simple synthesis of magnetic nanoparticles-supported 4-aminomethylbenzoic acid as a highly efficient and reusable catalyst for synthesis of 2-amino-4H-chromene derivatives

A new 4-aminomethylbenzoic acid-functionalized Fe3O4 magnetic nanoparticles as a hybrid heterogeneous catalyst was synthesised and characterized by FT-IR, XRD, TGA, TEM, SEM and VSM techniques. The catalytic activity of this nanocata

Immobilized piperazine on the surface of graphene oxide as a heterogeneous bifunctional acid-base catalyst for the multicomponent synthesis of 2-amino-3-cyano-4: H -chromenes

Immobilized piperazine on the surface of graphene oxide (piperazine-GO) is synthesized and characterized by different methods such as FT-IR, solid-state 29Si{1H} and 13C{1H} CP/MAS NMR, elemental analysis, TGA, TEM, FE-SEM, XPS, and TPD. Subsequently, it is used as a heterogeneous bifunctional acid-base catalyst for the efficient multicomponent reaction of malononitrile, different active compounds containing enolizable C-H bonds and various aryl/alkyl aldehydes in aqueous ethanol. A wide variety of 2-amino-3-cyano-4H-chromenes are synthesized in the presence of this heterogeneous catalyst in good to high yields and with short reaction times. The catalyst is easily separated and reused for at least six times without significant loss of activity. The acidic nature of GO improves the catalytic activity of the supported piperazine and also provides heterogeneity to the catalyst. Use of aqueous ethanol as a green solvent, high turnover numbers (TON), facile catalyst recovery and reuse, simple work-up and generality of the method make this protocol an environmentally benign procedure for the synthesis of the title heterocycles.

MCM-41@Schiff base-Co(OAc)2 as an efficient catalyst for the synthesis of pyran derivatives

Heterogeneous ordered mesoporous silica materials catalyst, MCM-41@Schiff base-Co(AcO)2, reveals high catalytic performance within the synthesis of pyran derivatives using the multicomponent reaction of aldehydes, malononitrile and 2-naphthol (

Synthesis, molecular modeling and BACE-1 inhibitory study of tetrahydrobenzo[b] pyran derivatives

β-Secretase (BACE1) has been broadly documented as one of the possible therapeutic targets for the treatment of Alzheimer's disease. In this paper, we report the synthesis and the for β-secretase (BACE-1) inhibitory activity of new series of tetrahydroben

2-Hydroxyethyl-1-ammonium 3-hydroxypropane-1-sulfonate: a biodegradable and recyclable ionic liquid for the one-pot synthesis of 2-amino-3-cyano-4H-pyrans

2-Hydroxyethyl-1-ammonium 3-hydroxypropane-1-sulfonate ‘HAHS’ was synthesized as a novel ionic liquid and characterized by various techniques. ‘HAHS’ ionic liquid was efficiently applied as a multifunctional promoter for the three-component synthesis of 2