23932-84-5

Usage

Uses

Used in Organic Synthesis:
6-Fluoro-3H-isobenzofuran-1-one is used as a building block for the synthesis of various pharmaceutical and agrochemical products. Its unique structure and fluorine atom contribute to the development of new compounds with improved properties and applications.
Used in Pharmaceutical Research:
6-Fluoro-3H-isobenzofuran-1-one is utilized in pharmaceutical research due to its potential biological activities. It serves as a key intermediate in the development of novel drugs with therapeutic potential.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-Fluoro-3H-isobenzofuran-1-one is employed for its potential applications in drug discovery. Its unique properties and reactivity make it a promising candidate for the design and synthesis of new therapeutic agents.
Used in Drug Discovery:
6-Fluoro-3H-isobenzofuran-1-one plays a significant role in drug discovery, where it is studied for its potential to contribute to the development of innovative medications. Its presence in various synthetic pathways allows researchers to explore its potential in treating various diseases and conditions.

Upstream product

• 229027-89-8 (2-bromo-4-fluorophenyl)methanol 
• 57319-65-0 6-aminophthalide 
• 138786-65-9 methyl 2-(bromomethyl)-5-fluorobenzoate 
• 62558-08-1 4-fluoro-2-(hydroxymethyl)benzyl alcohol 
• 57584-70-0 5-fluoro-1,3-dihydroisobenzofuran 
• 59142-68-6 2-bromo-4-fluorobenzaldehyde 
• 124-38-9 carbon dioxide 
• 459-56-3 4-fluorobenzylic alcohol 
• 33184-16-6 5-fluoro-2-methylbenzoic acid 
• 319-03-9 4-fluorophthalic anhydride 
• 455-38-9 3-fluorobenzoic acid 
• 74-95-3 1,1-dibromomethane 

Downstream Products

• 81890-53-1 5-fluoro-2-(4-fluorophenylthiomethyl)benzoic acid 
• 114312-62-8 2-<(3-Fluorophenyl)oxymethyl>-5-fluorobenzoic acid 
• 81890-52-0 5-fluoro-2-[(phenylthio)methyl]benzoic acid 
• 191934-72-2 2-(chloromethyl)-5-fluorobenzoyl chloride 
• 1341091-61-9 5-fluoro-2-(hydroxymethyl)benzoic acid 
• 920481-01-2 5-fluoro-2-formylbenzoic acid 
• 1352835-21-2 2-((3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylamino)methyl)-5-fluorobenzoic acid 
• 1194374-71-4 methyl 5-fluoro-2-formylbenzoate 
• 114312-33-3 (E)-1-(3,9-Difluoro-6,11-dihydrodibenzoxepin-11-yl)-4-(3-phenyl-2-propenyl)piperazine dimaleate 
• 139305-40-1 (E)-1-(2,9-Difluoro-6,11-dihydrodibenzoxepin-11-yl)-4-(3-phenyl-2-propenyl)piperazine dimaleate 

Relevant academic research and scientific papers

Fast microwave promoted palladium-catalyzed synthesis of phthalides from bromobenzyl alcohols utilizing DMF and Mo(CO)6 as carbon monoxide sources

A fast method utilizing in situ generated CO for the synthesis of phthalides has been developed. DMF and Mo(CO)6 were applied as two alternative CO-sources in these microwave promoted carbonylation-lactone formation reactions. Mo(CO)6 was found to be the more generally applicable CO-source and provided phthalides as well as dihydroisocoumarin, dihydroisoindone, and phthalimide from the corresponding aryl bromide via an efficient CO insertion within a 1h reaction time.

NOVEL COMPOUNDS USEFUL AS POLY(ADP-RIBOSE) POLYMERASE (PARP) INHIBITORS

The present invention provides novel poly(ADP-ribose) polymerase (PARP) inhibitors, methods of preparing them, pharmaceutical compositions containing them and methods for the treatment, prevention and/or amelioration of PARP mediated diseases or disorders using them. In particular, the compounds described herein are useful for the treatment of carcinoma of the breast, ovarian cancer, carcinoma of the liver, carcinoma of the lung, small cell lung cancer, esophageal cancer, gall bladder cancer, pancreatic cancer and stomach cancer.

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.

Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids

A mild and practical C(sp3)-H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.

Squaramide-catalyzed asymmetric intramolecular oxa-michael reaction of α,β-unsaturated carbonyls containing benzyl alcohol: Construction of chiral 1-substituted phthalans

Organocatalytic enantioselective intramolecular oxa-Michael reactions of benzyl alcohol bearing α,β-unsaturated carbonyls as Michael acceptors are presented herein. Using cinchona squaramide-based organocatalyst, enones as well as α,βunsaturated esters containing benzyl alcohol provided their corresponding 1,3-dihydroisobenzofuranyl-1-methylene ketones and 1,3-dihydroisobenzofuranyl-1-methylene esters in excellent yields with high enantioselectivities. In addition, enantioenriched 1,3-dihydroisobenzofuranyl-1-methylene ketone could be obtained from the Wittig/oxa-Michael reaction cascade of 1,3-dihydro-2-benzofuran-1-ol.

Organocatalytic enantioselective synthesis of phthalans via Wittig/oxa-Michael cascade reaction

An enantioselective synthetic method for 1-substituted phthalans has been developed. The organocatalytic reaction between 1,3-dihydro-2-benzofuran-1-ols and Wittig reagents using cinchona squaramide-based organocatalyst proceeded with sequential Wittig reaction followed by an enantioselective intramolecular oxa-Michael reaction, yielding enantioenriched phthalans with moderate to good enantioselectivities.

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.

Platinum-on-Carbon-Catalyzed Aqueous Oxidative Lactonization of Diols by Using Molecular Oxygen

A lactonization of various diols catalyzed by platinum on carbon (Pt/C) in water under an atmosphere of molecular oxygen was developed. Derivatives of 1,4- 1,5- and 1,6-diols were transformed into the corresponding five-, six-, and seven-membered lactones by the present oxidative lactonization method.

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.

Discovery of potent indenoisoquinoline topoisomerase i poisons lacking the 3-nitro toxicophore

3-Nitroindenoisoquinoline human topoisomerase IB (Top1) poisons have potent antiproliferative effects on cancer cells. The undesirable nitro toxicophore could hypothetically be replaced by other functional groups that would retain the desired biological activities and minimize potential safety risks. Eleven series of indenoisoquinolines bearing 3-nitro bioisosteres were synthesized. The molecules were evaluated in the Top1-mediated DNA cleavage assay and in the National Cancer Institute's 60 cell line cytotoxicity assay. The data reveal that fluorine and chlorine may substitute for the 3-nitro group with minimal loss of Top1 poisoning activity. The new information gained from these efforts can be used to design novel indenoisoquinolines with improved safety.