111478-49-0

Basic information

• Product Name: 2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE
• Synonyms: 4H-1-Benzopyran-4-one, 2,3-dihydro-2,2-dimethyl-6-nitro-;2,2-diMethyl-6-nitro-3,4-dihydro-2H-1-benzopyran-4-one;2,3-Dihydro-2,2-dimethyl-6-nitro-4H-1-benzopyran-4-one
• CAS NO: 111478-49-0
• Molecular Formula: C11H11NO4
• Molecular Weight: 221.21
• Mol File: 111478-49-0.mol

Chemical Properties

• Melting Point: 373℃
• Boiling Point: 365.9°Cat760mmHg
• Flash Point: 171.1°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 1.52E-05mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE(111478-49-0)
• EPA Substance Registry System: 2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE(111478-49-0)

Safety Data

• Hazardous Substances Data: 111478-49-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE is used as a research compound for its potential pharmacological activities, such as antioxidant, anti-inflammatory, and neuroprotective properties. It is being studied for its potential use in the treatment of various diseases, including cancer and neurodegenerative disorders.
Used in Organic Synthesis:
2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE is used as a key intermediate in the synthesis of various organic compounds, particularly in the development of new pharmaceutical agents.
Used in Medicinal Chemistry:
2,2-DIMETHYL-6-NITRO-CHROMAN-4-ONE is used as a subject of interest for further research and development in the field of medicinal chemistry, due to its promising results in preclinical studies and potential applications in the treatment of various diseases.

InChI:InChI=1/C11H11NO4/c1-11(2)6-9(13)8-5-7(12(14)15)3-4-10(8)16-11/h3-5H,6H2,1-2H3

Upstream product

• 1450-76-6 1-(2-hydroxy-5-nitrophenyl)ethanone 
• 67-64-1 acetone 
• 3780-33-4 2,3-dihydro-2,2-dimethylbenzo[b]pyran-4-one 
• 100-02-7 4-nitro-phenol 
• 3350-78-5 3,3-Dimethylacryloyl chloride 

Downstream Products

• 33143-28-1 6-nitro-2,2-dimethyl chromene 
• 135082-85-8 2,2-dimethyl-2H-1-benzopyran-6-amine 

Relevant articles and documents

2,2-Dimethyl-6-nitro-3,4-dihydro-2H-benzo[b]pyran-4-one O-benzoyloxime

The title compound, C18H16N2O5, has a pyran ring in a half-chair conformation fused to a benzene ring. The substituent groups at C3 and C5 are approximately coplanar with the benzopyran nucleus, with dihedral angles of 8.5 (5) and 4.2 (5)°, respectively. The benzoyloxy carbonyl group and the benzene ring of the benzopyran moiety both adopt a cis configuration.

An Efficient Synthesis of 6-oxa-spiro[3.4]octan-1-one Derivates Through 3-diazochroman-4-one and Alkene

Spiro[2,2-dimethyl-benzofuran,bicyclo [4.2.0]octane]-7′-one with fused and spirocyclic oxygen-containing rigid skeleton structure is obtained via Wolff rearrangement and cycloaddition with good yields. Then Spiro[2,2-dimethyl-benzofuran,hexahydro-isobenzofuran]-7′-one is synthesized by further Baeyer-Villiger oxidation. These two kinds of products have a special fused and spirocyclic oxygen-containing rigid skeleton structure and are reported by our group. (Figure presented.).

Identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives as potassium channel activators and anti-inflammatory agents

The present study described the design, synthesis and identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives. Their biological activity was tested for KATP channel opener as antihypertensives, COX-1 and COX-2 activity. The results were compared with the activity of cromakalim, ibuprofen and celecoxib. The study aimed at exploring the influence of introduction of a benzoxazine substituent at position 6 of various derivatives of benzopyrans in order to improve biological activity. Several compounds were found to be equipotent or even more potent than cromakalim. Out of these nitro-substituted benzopyrans, nitro substitution at benzoxazino group possessed potent antihypertensive activity in the R/S isomers. With amino derivatives, activity remains constant when compared with standard cromakalim. Similarly, compounds 17b, 17c, 17e and 17h have exhibited around 40 % inhibition of COX-1 as compared to the inhibition of COX-2. Only two compounds 17g and 17i exhibited effective inhibition more than 50 % of COX-2 compared with the inhibition of COX-1 at a concentration of 0.3 mg/ml.

N-(2,7-dimethyl-2-alkyl-2H-chromen-6-yl)sulfonamide derivatives as selective serotonin 5-HT6 receptor antagonists: Design, synthesis, and biological evaluation

Serotonin 5-HT6 receptor, which is predominantly expressed in the central nervous system, is a valuable therapeutic target. Serotonin 5-HT6 receptor antagonists have potential for the treatment of various diseases that include psychotic disorders, dementia, depression, and obesity. In this study, we designed and synthesized the N-(2,7-dimethyl-2-alkyl-2H-chromen-6-yl)sulfonamide-based library as a potential serotonin 5-HT6 receptor antagonist. The library was subjected to a series of binding affinity tests to identify the lead compound, and check the selectivity of test compounds towards the 5-HT6 receptor. Accordingly, compound 6m was identified as the most active compound, with IC50 = 87 nM. The binding affinity of 95.3% of 6m (10 μM) with the 5-HT6 receptor among other serotonin 5-HT1a, 5-HT2a, 5-HT2c, and 5-HT7, and dopamine receptors D1, D2, D3, and D4, demonstrated the high selectivity of 6m towards the 5-HT6 receptor.

Expeditious photochemical reaction toward the preparation of substituted chroman-4-ones

A facile photochemical preparation of 5-, 6-, and 7-substituted chroman-4-ones from aryl 3-methyl-2-butenoate esters is described. The two-phase base-catalyzed method relies upon two consecutive processes in one-pot reaction through a photo-Fries rearrangement and a based-catalyzed intramolecular oxa-Michael addition to afford the desired products.

An excellent protocol for the synthesis of benzopyrans using basic resin under MWI

A convenient, microwave promoted novel protocol for the synthesis of diverse kinds of substituted benzopyrans from the corresponding variety of substituted hydroxy acetophenones and keto compounds using Amberlite IRA 400 resin (basic resin) under solvent-free conditions, has been developed. This protocol is mild and more efficient than the other reported methods.

Microwave assisted facile and efficient synthesis of benzopyran

A convenient, fast and high yielding method for the preparation of 3,4-dihydrobenzopyrans has been achieved by the condensation of various acetophenones with different keto compounds in the presence of a base, assisted by microwave activation under solvent free conditions with or without use of a solid support.

Hydroxyacetic acid derivatives for the treatment of diabetic complications

Racemic and chiral (2R,4R)-4-c-hydroxy-2-4-(substituted)chroman(and thiochroman)-4-acetic acids and their pharmaceutically acceptable salts, their use in the treatment of diabetic complications and intermediates therefor.