2211-83-8

Usage

InChI:InChI=1/C9H8O2/c1-6-3-2-4-7-8(6)5-11-9(7)10/h2-4H,5H2,1H3

Upstream product

• 4792-30-7 3-methylphthalic acid anhydride 
• 74-95-3 1,1-dibromomethane 
• 99-04-7 m-Toluic acid 
• 89-95-2 2-methyl-benzyl alcohol 
• 124-38-9 carbon dioxide 
• 131524-43-1 methyl 2-formyl-3-hydroxybenzoate 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 13161-32-5 4-hydroxy-3H-isobenzofuran-1-one 
• 534-22-5 2-methylfuran 
• 6345-56-8 1-methyl-7-oxa-bicyclo[2.2.1]heptane-2endo,3endo-dicarboxylic acid anhydride 
• 75-16-1 methylmagnesium bromide 
• 603-79-2 2,3-dimethylbenzoic acid 
• 127168-91-6 methyl 2,3-bis(bromomethyl)benzoate 
• 15012-36-9 methyl 2,3-dimethylbenzoate 

Downstream Products

• 90484-24-5 1-oxo-1,3-dihydro-isobenzofuran-4-carbaldehyde 
• 72288-75-6 3-hydroxy-4-methylisobenzofuran-1(3H)-one 

Relevant academic research and scientific papers

Chiral Bicyclic Imidazole-Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters

Utilizing a chiral bicyclic imidazole organocatalyst and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3-hydroxyphthalides through enantioselective acylation (up to 99 % ee). The computational studies suggest a general base catalytic mechanism differing from the widely accepted nucleophilic catalytic mechanism. The structure analysis of the key transition states shows that the CH-π interactions and not the previously considered cation/π-π interactions between the catalyst and substrate is the dominant factor giving rise to the observed stereocontrol.

Enantioselective synthesis of 3-aryl-phthalides through a nickel-catalyzed stereoconvergent cross-coupling reaction

A nickel-catalyzed asymmetric Suzuki-Miyaura cross-coupling of racemic 3-bromo-phthalides and arylboronic acids was realized for the synthesis of diverse chiral 3-aryl-phthalides in moderate to excellent reaction yields. The reaction proceeded in a stereoconvergent manner and high enantioselectivities were observed for most examined examples. A number of functional groups like aldehyde, ester and bromide were well tolerated. Heteroaromatic boronic acids were also competent coupling partners in this reaction.

Ligand-enabled pd(ii)-catalyzed c(sp3)-h lactonization using molecular oxygen as oxidant

Pd(II)-catalyzed C-H lactonization of o-methyl benzoic acid substrates has been achieved using molecular oxygen as the oxidant. This finding provides a rare example of C-H oxygenation through Pd(II)/Pd(0) catalysis as well as a method to construct biologically important benzolactone scaffolds. The use of a gas mixture of 5% oxygen in nitrogen demonstrated the possibility for its application in pharmaceutical manufacturing.

Incorporation of carbon dioxide into phthalides: Via ligand-free copper-catalyzed direct carboxylation of benzoxasiloles

The direct carboxylation of benzoxasiloles with carbon dioxide proceeded smoothly under mild conditions using copper iodide as a catalyst to afford phthalides after an acid work-up. Broad substrate scope and application of this methodology for the synthesis of natural products highlight the synthetic utility of this protocol.

Dehydrogenative lactonization of diols in aqueous media catalyzed by a water-soluble iridium complex bearing a functional bipyridine ligand

A new catalytic system for the dehydrogenative lactonization of a variety of benzylic and aliphatic diols in aqueous media was developed. By using a water-soluble, dicationic iridium catalyst bearing 6,6′-dihydroxy-2, 2′-bipyridine as a functional ligand, highly atom economical and environmentally benign synthesis of various lactones was achieved in good to excellent yields. Recovery and reuse of the catalyst were also accomplished by a simple phase separation and the recovered catalyst maintained its high activity at least until the fifth run. Copyright

Total synthesis of neo-tanshinlactones through a cascade benzannulation-lactonization as the key step

The cascade annulation-lactonization of phthalides with α-carboxyfurylacrylates in the presence of lithium hexamethyldisilazide (LiHMDS) provides both convergent and semiconvergent regioselective syntheses of neo-tanshinlactones in moderate yields. This methodology also offers an avenue for the direct syntheses of hitherto unreported 6-alkoxycarbonyl-substituted neo-tanshinlactones and their heterocyclic analogues. A new synthesis of 4-alkyl phthalides was developed on the basis of a combination of a Duff reaction and Fuerstner cross-coupling. The cascade benzannulation-lactonization of phthalides with α-carboxyfurylacrylates was employed as the key reaction for the concise synthesis of neo-tanshinlactone. Copyright

Reduction of Ag(I) by 1-acyl-2-arylhydrazines: Mechanism of photographic infectious development

The photographic process of 'infectious development' in which 1-acyl-2-arylhydrazines reduce Ag(I) has been studied using analogues. 1-Acyl-2-aryldiazenes, resulting from oxidation of 1-acyl-2-arylhydrazines, are hydrolysed to anions of aryldiazenes (ArN = NH), which undergo further oxidation with loss of nitrogen to yield aryl radicals. The aryl radicals cause 'feedback inhibition' which is prevented by the addition of benzhydrol.

Aromatic Spiranes XXI [1]: Syntheses of Methyl Substituted Phthalaldehydic Acids and their Ethyl and Methyl Esters as Synthones for Syntheses of Methylated 2,2′-Spirobiindandiones

The isomeric methyl phthalaldehydic acids 11 were obtained from phthalides 4 by bromation (NBS) to the 3-bromo derivatives 7 and subsequent hydrolysis with water. 4 in turn were accessible from dimethyl methyl benzoates 1 by dibromination with NBS and subsequent thermical cyclization to the bromo derivatives 3 which, on catalytic dehalogenation, afforded the phthalides 4. Reaction of 11 with methanol or ethanol gave the pseudo-esters 13 and 14, resp. Short treatment of 11 with diazomethane on the other hand yielded the methyl formyl benzoates 15b to 15e. Prolonged reaction (several hours) gave the oxiranyl compounds 17; in addition, the acetonyl derivatives 18 were also found, obviously formed by a double methylene insertion into 15. All reactions proceeded with good to excellent yields.

REGIOSELECTIVE SYNTHESIS OF SUBSTITUTED PHTHALIDES VIA INTRAMOLECULAR "DIENE-REGENERATIVE" DIELS-ALDER REACTION OF 2-PYRONES

Some 2-pyrone-6-carboxylates bearing appropriate dienophiles in ester moieties underwent "diene-regenerative" Diels-Alder reaction to afford the dihydrophthalides, which were aromatized to phthalide derivatives in the presence of palladium-charcoal.In these reactions the substituents at 4 or 7-position of phthalides arose from those on yhe dienophile moieties in the starting 2-pyrones.

Secondary amines, their preparation and use in pharmaceutical compositions

The compounds of the formula (II): STR1 and their pharmaceutically acceptable salts wherein R1 is a hydrogen, fluorine or chlorine atom or a hydroxyl, hydroxymethyl, methyl, methoxyl, amino, formamido, acetamido, methylsulphonylamido, nitro, benzyloxy, methylsulphonylmethyl, ureido, trifluoromethyl or p-methoxybenzylamino group; R2 is a hydrogen, fluorine or chlorine atom or a hydroxyl group; R3 is a hydrogen or chlorine atom or a hydroxyl group; R4 is a carboxylic acid group or a salt, ester or amide thereof; R5 is a hydrogen, chlorine or fluorine atom or a methyl, methoxyl or hydroxyl group or a carboxylic acid group or a salt, ester or amide thereof; R6 is a hydrogen atom or a methyl, or propyl group; X is an oxygen atom or a bond; and Y is an alkylene group of up to 6 carbon atoms or a bond have been found to possess anti-obesity and/or antihyperglycaemic activity.