2688-48-4

Usage

Uses

Used in Organic Synthesis:
Homogentisic Acid γ-Lactone is used as an intermediate in the synthesis of various organic compounds. Its unique chemical structure allows it to serve as a building block for the development of a wide range of products, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Homogentisic Acid γ-Lactone is used as a key component in the development of drugs targeting specific medical conditions. Its role in organic synthesis enables the creation of novel drug candidates with potential therapeutic benefits.
Used in Agrochemical Industry:
Homogentisic Acid γ-Lactone also finds application in the agrochemical industry, where it is utilized in the synthesis of compounds with pesticidal, herbicidal, or fungicidal properties. This contributes to the development of more effective and environmentally friendly solutions for crop protection and management.
Used in Specialty Chemicals:
The compound is also employed in the production of specialty chemicals, which are tailored to meet the specific requirements of various industries, such as cosmetics, coatings, and plastics. Its versatility in organic synthesis makes it a valuable asset in the development of innovative and high-performance products.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 363, 1980 DOI: 10.1021/jo01290a038

InChI:InChI=1/C8H6O3/c9-6-1-2-7-5(3-6)4-8(10)11-7/h1-3,9H,4H2

Upstream product

• 76196-46-8 ethyl 2-(2,5-dihydroxyphenyl)acetate 
• 2503-24-4 5-methoxybenzofuran-2(3H)-one 
• 106-51-4 p-benzoquinone 
• 51385-18-3 2-(2-hydroxy-5-methoxyphenyl)acetic acid 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 298-12-4 Glyoxilic acid 
• 637-88-7 1,4-Cyclohexanedione 
• 35227-78-2 diethyl (ethoxymagnesio)malonate 
• 106551-22-8 2-(N-methylanilino)benzofuran-5-ol 
• 1758-25-4 (2,5-dimethoxyphenyl)acetic acid 
• 451-13-8 homogentisic acid 
• 860183-06-8 2-ethoxy-benzofuran-5-ol 

Downstream Products

• 22122-82-3 2-benzothiazol-2-ylmethyl-benzene-1,4-diol 
• 132513-38-3 5-hydroxy-2-(4'-hydroxyphenyl)-3-benzofurancarboxylic acid 
• 27439-06-1 5-hydroxy-3-[(4-hydroxyphenyl)methylidene]-benzo[b]furan-2-one 
• 107680-51-3 4',5-Diacetoxy-benzalisocumaranon 
• 107680-50-2 (Z)-5-hydroxy-3-<(4-hydroxyphenyl)methylene>-2(3H)-benzofuranone 
• 1257404-82-2 JC₀₂₅ 
• 1253057-48-5 3-chlorobenzoic acid (2-oxo-2,3-dihydro-benzofuran-5-yl)ester 
• 1253057-47-4 benzoic acid (2-oxo-2,3-dihydro-benzofuran-5-yl)ester 

Relevant academic research and scientific papers

Total synthesis of clavatadine A

The first total synthesis of the potent and selective human blood coagulation factor XIa inhibitor clavatadine A (1) is described. Direct, early-stage guanidinylation enabled rapid, convergent access to an immediate clavatadine A precursor. Concomitant lactone hydrolysis and guanidine deprotection with aqueous acid cleanly provided clavatadine A (1) in only four steps (longest linear sequence, 41-43% overall yield).

Lewis acid promoted synthesis of 2(3H)-benzofuranones

A Lewis acid promoted one-step synthesis of 2(3H)-benzofuranones via an intramolecular rearrangement of the corresponding substituted O-methoxyacetylbenzenes and coumarins is described.

Isoaurones: synthesis and stereochemical assignments of geometrical isomers

A series of isoaurones have been synthesized for the first time from substituted acetophenones via benzo-2(3H)-furanone in three steps. Geometrical isomers of the isoaurones were separated. The differences in the proton and carbon NMR spectra of the E- and Z-isoaurones afford a useful method for distinguishing between the two isomers. Marginalin, a metabolite of Dytiscus marginalis has been synthesized and the spectral data of the synthetic E-isomer were in good agreement with those of the natural product. The antioxidant activity of isoaurones was determined by superoxide free radical (NBT) method and isoaurones 12 and 13 displayed excellent antioxidant activity.

Synthesis of 5-hydroxyoxaindan-2-ones and indol-5-ols from 1,4- cyclohexanedione

1,4-Cyclohexanedione reacted with 2-oxocarboxylic acids to give 5- hydroxyoxaindan-2-ones including homogentisic lactone in one pot. The obtained aromatic compounds were transformed into indol-5-ols in a few steps. The sequential reactions showed a significance of 1,4-cyclohexanedione as a starting material in aromatic synthesis and an alternative access to the indol-5-ols.

Ketene S,N-Acetals as Synthetic Intermediates for Heterocycles. Reaction of Ketene S,N-Acetals with 1,4-Quinones

Annelation of ketene S,N-acetals with 1,4-quinones is found to give benzo- and naphthofurans bearing enamine groups.Subsequent enamine reaction allows the formation of 1-benz- and naphthooxepines and benzofuran-2-ones.