2292-60-6

Usage

Structure

1H-2-Benzopyran, 3,4-dihydro-1-(4-methoxyphenyl)-

Natural occurrence

Found in various plant species

Pharmacological properties

Exhibits antioxidant, anti-inflammatory, and anti-cancer activities, as well as potential neuroprotective effects

Traditional medicine

Has been investigated for its role in traditional medicine

Potential as a source of novel drug candidates

Studies have shown that 1H-2-Benzopyran, 3,4-dihydro-1-(4-methoxyphenyl)- has the potential to be used in the development of new medicines for various health conditions.

Upstream product

• 60-12-8 2-phenylethanol 
• 123-11-5 4-methoxy-benzaldehyde 
• 493-05-0 isochromane 
• 100-66-3 methoxybenzene 
• 4702-34-5 isochroman-1-one 
• 14774-77-7 p-methoxyphenyllithium 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 34818-49-0 1-methoxyisochromane 
• 110534-46-8 diethyl (p-methoxyphenyl)boronate 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 2318-17-4 2-(2-Brom-aethyl)-4'-methoxy-benzophenon 
• 1224455-55-3 (2-(2-hydroxyethyl)phenyl)(4-methoxyphenyl)methanone 

Relevant academic research and scientific papers

Oxidative Kinetic Resolution of Cyclic Benzylic Ethers

A manganese-catalyzed oxidative kinetic resolution of cyclic benzylic ethers through asymmetric C(sp3)?H oxidation is reported. The practical approach is applicable to a wide range of 1,3-dihydroisobenzofurans bearing diverse functional groups and substituent patterns at the α position with extremely efficient enantiodiscrimination. The generality of the strategy was further demonstrated by efficient oxidative kinetic resolution of another type of five-membered cyclic benzylic ether, 2,3-dihydrobenzofurans, and six-membered 6H-benzo[c]chromenes. Direct late-stage oxidative kinetic resolution of bioactive molecules that are otherwise difficult to access was further explored.

Direct oxidative C(sp3)–H cyanation of secondary benzylic ethers

Current studies on the oxidative C–H functionalization of benzylic ethers for C–C forging process dominantly focus on primary ethers. The corresponding reaction of secondary ethers remains underdeveloped. Herein, a practical and efficient oxidative C–H cyanation of secondary benzylic ethers with TMSCN in the presence of DDQ is described. The metal-free process is well tolerated with a wide variety of electronically varied α-monosubstituted isochromans, facilely furnishing a library of isochromans bearing α-aryl α-cyano substituent patterns for further diversification and bioactive small molecule identification.

Transition-Metal-Free Cross-Coupling of Indium Organometallics with Chromene and Isochroman Acetals Mediated by BF3·OEt2

A transition-metal-free coupling of triorganoindium reagents with benzopyranyl acetals mediated by a Lewis acid has been developed. The reaction of R3In with chromene and isochroman acetals in the presence of BF3·OEt2 afforded 2-substituted chromenes and 1-substituted isochromans, respectively, in good yields. The reactions proceed with a variety of triorganoindium reagents (aryl, heteroaryl, alkynyl, alkenyl, alkyl) using only 50 mol % of the organometallic, thus demonstrating the efficiency of these species. Preliminary mechanistic studies indicate the formation of an oxocarbenium ion intermediate in the presence of the Lewis acid.

Efficient C(sp3)-H bond functionalization of isochroman by azadol catalysis

A novel organocatalytic C(sp3)-H bond functionalization of isochroman under practical conditions has been developed. In the presence of 5.0 mol % of AZADOL, the catalysis proceeded successfully with a broad range of substrates and nucleophiles in excellent yields.

Structurally diverse α-substituted benzopyran synthesis through a practical metal-free C(sp3)-H functionalization

A trityl ion-mediated practical C-H functionalization of a variety of benzopyrans with a wide range of nucleophiles (organoboranes and C-H molecules) at ambient temperature has been disclosed. The metal-free reaction has an excellent functional group tole

Oxidative arylation of isochroman

We report the use of a previously intractable nucleophile, anisole, in an oxidative "cross-dehydrogenative coupling" (CDC) reaction with the cyclic ether isochroman, as well as derivatives of both components. Metal catalysis was required for the reaction

Zeolite-catalyzed simple synthesis of isochromans via the oxa-Pictet-Spengler reaction

The synthesis of isochromans via oxa-Pictet-Spengler reaction using a modified small pore size zeolite E4 as catalyst was investigated. Ersorb-4 (E4) is a clinoptylolite-type zeolite material with high silicon content. The reaction of 2-phenylethanol deri