491-31-6

Usage

Uses

Used in Pharmaceutical Industry:
1H-2-Benzopyran-1-one is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
1H-2-Benzopyran-1-one serves as a versatile building block in organic chemistry, enabling the creation of a wide range of chemical compounds with diverse properties and applications.
Used in Research and Development:
Due to its unique structure and reactivity, 1H-2-Benzopyran-1-one is utilized in research and development for the exploration of new chemical reactions, mechanisms, and potential applications in various industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 5274, 1984 DOI: 10.1021/ja00330a041Journal of Heterocyclic Chemistry, 27, p. 1419, 1990 DOI: 10.1002/jhet.5570270544Tetrahedron Letters, 25, p. 4459, 1984 DOI: 10.1016/S0040-4039(01)81466-0

InChI:InChI=1/C9H6O2/c10-9-8-4-2-1-3-7(8)5-6-11-9/h1-6H

Upstream product

• 90-15-3 α-naphthol 
• 35847-40-6 1-diazo-(1H)-indene 
• 74-85-1 ethene 
• 65-85-0 benzoic acid 
• 135-19-3 β-naphthol 
• 480-90-0 1H-inden-1-one 
• 62252-26-0 JLK 6 
• 103-71-9 phenyl isocyanate 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 524-42-5 1,2-naphthoquinone 
• 105-38-4 vinyl propionate 
• 27326-43-8 2-vinylbenzoic acid 
• 78364-23-5 4-Methoxymethylen-3,4-dihydro-1H-2-benzopyran-1,3-dion 

Downstream Products

• 96719-92-5 2-[2-(3-Methoxy-phenyl)-ethyl]-2H-isoquinolin-1-one 
• 62499-91-6 2-(formylmethyl)benzoic acid 
• 493-05-0 isochromane 
• 6346-00-5 2-(2-hydroxyethyl)benzyl alcohol 
• 4702-37-8 1-Thio-isocumarin 
• 62827-73-0 3-(4-methylphenyl)-1H-isochromen-1-one 
• 66193-87-1 2-amino-1,2-dihydroisoquinolin-1(2H)-one 
• 3297-72-1 1-phenylisoquinoline 
• 96719-95-8 2-[2-(3-Methoxy-phenyl)-ethyl]-1,2,3,4-tetrahydro-isoquinoline; hydrochloride 
• 96719-96-9 2-[2-(3-Methoxy-phenyl)-ethyl]-1,2,3,4,5,6,7,8-octahydro-isoquinoline; hydrochloride 
• 96719-93-6 2-[2-(3-Methoxy-phenyl)-ethyl]-3,4-dihydro-2H-isoquinolin-1-one 
• 96719-94-7 2-[2-(3-Methoxy-phenyl)-ethyl]-3,4,5,6,7,8-hexahydro-2H-isoquinolin-1-one 
• 491-30-5 1-hydroxyisoquinoline 
• 21201-50-3 2-Hydroxyisocarbostyril 

Relevant academic research and scientific papers

Ag(i)-Promoted homo-dimerization of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenesviaa [4 + 2] cycloaddition of benzopyrylium ions: access to structurally unique naphthalenes

Herein we report a Ag(i)-promoted homo-dimerization of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes for the synthesis of structurally novel and functionalized naphthalene derivatives. This transformation exhibits a broad scope for the alkyl as well as aryl groups present on alkynes. Observations made from control experiments suggest the possible mechanism as (i) the homo-dimerization of thein situgenerated benzopyrylium ion intermediates through a head-tail [4 + 2] cycloaddition, followed by (ii) the competitive ring-openingvs. decarbonylative aromatization of the adduct to give formylated and deformylated naphthalenes, respectively.

Dual Activity of Grubbs-Type Catalyst in the Transvinylation of Carboxylic Acids and Ring-Closing Metathesis Reactions

The development of a multifunctional catalyst, which mimics the promiscuity of enzymes, that would catalyze more than one chemical transformation in a single reaction vessel is one of the key points of modern sustainable chemistry. The results of our experiments indicated that Grubbs-type catalysts possess such multitask activity, catalyzing the transvinylation reaction of carboxylic acids without losing their original metathetic activity. This new activity of Grubbs catalysts was evidenced on several examples. It allows us to design a transvinylation/ring-closing metathesis (RCM) cascade reaction leading to the formation of endocyclic enol lactones from unsaturated carboxylic acids in an one-pot procedure. This unique ability of Grubbs catalyst to catalyze multiple mechanically distinct cascade reactions in a chemoselective way offers the new possibility for the synthesis of complex compounds from simple, easily accessible substrates.

Rhodium(I)-Catalyzed Decarbonylative Aerobic Oxidation of Cyclic α-Diketones: A Regioselective Single Carbon Extrusion Strategy

A rhodium-catalyzed decarbonylative aerobic oxidation of cyclic α-diketones has been developed for the first time, where the regioselective formations of α-pyrones and isocoumarins have been achieved. The current decarbonylative aerobic oxidation pathway proceeds via the C-C bond cleavage followed by a C-O bond formation, representing a biomimetic oxidation approach to unsaturated six-membered cyclic lactones. The unique ability of rhodium catalysts to induce the decarbonylative aerobic oxidation opens up a new synthetic toolbox that utilizes the "regioselective single carbon" extrusion strategy.

Reductive electrochemical formation of 6H-dibenzo[b,d]pyran-6-one and 2-benzopyran-1(1H)-one

In the present Letter several carbolactones (oxidative products) are obtained under aprotic cathodic conditions in the preparative scaled electrolysis of 1,2-quinones in a divided electrochemical cell and in the presence of oxygen. When 9,10-phenanthrenequinone is reduced 6H-dibenzo[b,d]pyran-6-one and [1,1′-biphenyl]-2,2′-dicarboxylic acid are obtained as major products. In the reduction of 1,2-naphthoquinone, 2-benzopyran-1(1H)-one, and 2-(2-carboxyethenyl)-benzoic acid were formed as main products. The proposed mechanism to explain the formation of these and other products, that involves an electron-transfer reaction to the oxygen in air, is now discussed.

Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters

Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure.

Total synthesis of coriandrin and 7-demethylcoriandrin via a new synthesis of isocoumarins

Indenone epoxides 8, prepared from the corresponding indenones, have been shown to undergo clean thermal rearrangement to give isocoumarins 10 in high yields. This synthesis of isocoumarins, when applied to oxaindace-none 7, resulted in the total synthesis of coriandrin (1). (C) 2000 Elsevier Science Ltd.

SUBSTITUTED ISOCOUMARINS

Substituted isocoumarins, their use in inhibiting serine proteases with chymotrypsin-like and elastase-like specificity and their roles as anti-inflammatory agents.

THE GENERATION AND PHOTOCHEMISTRY OF INDENONE O-OXIDE AND FLUORENONE O-OXIDE IN LOW TEMPERATURE MATRICES

The photolysis of diazoindene and diazofluorene at 12 K in N2 matrices containing O2 has been studied, using i.r. spectroscopy.The carbonyl oxides, indenone O-oxide and fluorenone O-oxide, were formed by the reaction of O2 with the corresponding carbenes, and under appropriate conditions could be detected as very photolabile species.Photolysis of indenone O-oxide gave indenone and isocoumarin; similar photolysis of fluorenone O-oxide gave fluorenone and dibenzopyran-6-one.