49660-56-2

Usage

Uses

Used in Pharmaceutical Research:
8-Methylchromanone is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its unique structure and properties. It plays a crucial role in the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
8-Methylchromanone is used as a building block in organic synthesis for the preparation of a wide range of organic compounds. Its versatile chemical properties allow it to be easily modified and incorporated into complex molecular structures.
Used in Antioxidant Applications:
8-Methylchromanone is used as an antioxidant agent for its ability to neutralize free radicals and protect cells from oxidative damage. This makes it a potential candidate for the prevention and treatment of various diseases associated with oxidative stress.
Used in Anti-Inflammatory Applications:
8-Methylchromanone is used as an anti-inflammatory agent due to its ability to reduce inflammation and alleviate symptoms associated with inflammatory conditions. Its potential use in this area could lead to the development of new treatments for various inflammatory diseases.
Used in Disease Treatment and Prevention:
8-Methylchromanone has shown promise in the treatment of various diseases and conditions, making it an important compound for drug discovery and development. Its potential applications in this area could lead to the development of new therapeutic agents for a wide range of health issues.

Upstream product

• 117543-37-0 4-chloro-8-methyl-2H-chromene 
• 117543-25-6 1-(3-Chloro-prop-2-ynyloxy)-2-methyl-benzene 
• 25268-05-7 3-(2-methylphenoxy)propanenitrile 
• 95-48-7 ortho-cresol 
• 5652-20-0 1-methyl-2-(2-propynyloxy)benzene 
• 25173-35-7 3-(2-methylphenoxy)propanoic acid 

Downstream Products

• 3722-72-3 8-methyl-chroman 
• 707-91-5 9-methyl-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one 
• 65017-39-2 8-methyl-4H-1-benzopyran-4-one 
• 1393824-77-5 N-(3-benzoyl-8-methyl-2H-chromen-4-yl)acetamide 

Relevant academic research and scientific papers

Acid activated montmorillonite K-10 mediated intramolecular acylation: Simple and convenient synthesis of 4-chromanones

3-Aryloxyproionic acids undergo intramolecular cyclization in the presence of AA.Mont.K-10 in toluene under reflux for 30–45 min in good to excellent yields. Phenyl ring bearing various substituents at the ortho, meta, para positions undergo this cyclization reaction. This method involves simple work up and amenable for large scale preparations. The heterogeneous acid treated catalyst can be regenerated and used for up to three cycles with minimum loss of activity.

Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.

Enantioselective organocatalytic fluorination-induced Wagner-Meerwein rearrangement

Cracked under strain: Strained allylic cyclobutanols and cyclopropanols readily undergo a ring expansion described by the title rearrangement. This reaction is promoted by catalytic amounts of 1 and displays high tolerance with respect to the substrate scope. The corresponding β-fluoro spiroketone products are isolated in high yields and with excellent stereoselectivities. EDG=electron-donating group, EWG=electron-withdrawing group. Copyright

An efficient synthesis of 4-chromanones

A two step efficient and practical synthesis of a variety of 4-chromanones is described. Phenols undergo a Michael addition to acrylonitriles in the presence of catalytic amounts of potassium carbonate and tert-butanol to generate the corresponding 3-aryloxypropanenitriles in 50-93% yields. Treatment of the resulting aryloxypropionitriles with 1.5 equiv of TfOH and 5 equiv of TFA, followed by an aqueous work up afforded 4-chromanones in moderate to excellent yields.

THERMAL BEHAVIOUR OF ARYL γ-HALOPROPARGYL ETHERS

A systematic study of the behaviour of aryl γ-halopropargyl ethers under thermal condition was undertaken.Aryl γ-bromopropargyl ethers 2 underwent unique transformation in N,N-diethylaniline (215 deg C, 6 h) giving rise to a mixture of products 3,4 and 5,whereas, under similar conditions aryl γ-chloropropargyl ethers 8, afforded 4-chlorochromenes, 9.A remarkable substituent and solvent effect has been observed in the thermolysis of these aryl γ-bromo and γ-chloropropargyl ethers, rendering this transformation as a method for the synthesis of a number of substituted 4-bromochromenes 3, 4-chlorochromenes 9 and chroman-4-ones 7.In contrast, solution thermolysis of aryl γ-iodopropargyl ether 11 afforded aryl propargyl ether 1 as the major product.

A SIMPLE ROUTE FOR THE SYNTHESIS OF 4-CHLOROCHROMENES AND CHROMAN-4-ONES

A one pot synthesis of a number of 4-chlorochromenes and chroman-4-ones was achived from γ-chloropropargyl aryl ethers proceeding through Claisen rearrangement, depending upon the solvent of choice.