56096-89-0

Usage

Chemical Properties

Off-white crystalline

InChI:InChI=1/C7H4FIO2/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3H,(H,10,11)

Upstream product

• 446-32-2 4-fluoroanthranilic acid 
• 459-57-4 4-fluorobenzaldehyde 
• 456-22-4 4-Fluorobenzoic acid 
• 909545-47-7 4-fluoro-2.iodobenzaldehyde 

Downstream Products

• 84589-14-0 4-fluoro-2-(4-isopropylphenylthio)benzoic acid 
• 134987-38-5 4-fluoro-2-(3-methoxyphenylthio)benzoic acid 
• 1453081-50-9 2-[5-(2-tert-butoxycarbonylamino-2-methoxycarbonylethyl)-2-methoxyphenylamino]-4-fluorobenzoic acid 
• 1453081-49-6 5-fluorodiphenyl-iodonium-2-carboxylate 
• 345-29-9 4-fluorosalicylic acid 
• 1257247-29-2 3-benzylidene-5-fluoroisobenzofuran-1(3H)-one 
• 1261678-05-0 methyl 2-iodo-4-fluorobenzoate 

Relevant academic research and scientific papers

Mechanistic Investigation of the Iron-Catalyzed Azidation of Alkyl C(sp3)-H Bonds with Zhdankin’s λ3-Azidoiodane

An in-depth study of the mechanism of the azidation of C(sp3)-H bonds with Zhdankin’s λ3-azidoiodane reagent catalyzed by iron(II)(pybox) complexes is reported. Previously, it was shown that tertiary and benzylic C(sp3)-H bonds of a range of complex molecules underwent highly site-selective azidation by reaction with a λ3-azidoiodane reagent and an iron(II)(pybox) catalyst under mild conditions. However, the mechanism of this reaction was unclear. Here, a series of mechanistic experiments are presented that reveal critical features responsible for the high selectivity and broad scope of this reaction. These experiments demonstrate the ability of the λ3-azidoiodane reagent to undergo I-N bond homolysis under mild conditions to form λ2-iodanyl and azidyl radicals that undergo highly site-selective and rate-limiting abstraction of a hydrogen atom from the substrate. The resultant alkyl radical then combines rapidly with a resting state iron(III)-azide complex, which is generated by the reaction of the λ3-azidoiodane with the iron(II)(pybox) complex, to form the C(sp3)-N3bond. This mechanism is supported by the independent synthesis of well-defined iron complexes characterized by cyclic voltammetry, X-ray diffraction, and EPR spectroscopy, and by the reaction of the iron complexes with alkanes and the λ3-azidoiodane. Reaction monitoring and kinetic studies further reveal an unusual effect of the catalyst on the rate of formation of product and consumption of reactants and suggest a blueprint for the development of new processes leading to late-stage functionalization of C(sp3)-H bonds.

IrIII-Catalyzed Selective ortho-Monoiodination of Benzoic Acids with Unbiased C?H Bonds

An iridium-catalyzed selective ortho-monoiodination of benzoic acids with two equivalent C?H bonds is presented. A wide range of electron-rich and electron-poor substrates undergo the reaction under mild conditions, with >20:1 mono/di selectivity. Importantly, the C?H iodination occurs selectively ortho to the carboxylic acid moiety in substrates bearing competing coordinating directing groups. The reaction is performed at room temperature and no inert atmosphere or exclusion of moisture is required. Mechanistic investigations revealed a substrate-dependent reversible C?H activation/protodemetalation step, a substrate-dependent turnover-limiting step, and the crucial role of the AgI additive in the deactivation of the iodination product towards further reaction.

Direct carbocyclizations of benzoic acids: Catalyst-controlled synthesis of cyclic ketones and the development of tandem aHH (acyl Heck-Heck) reactions

The formation of exo-methylene indanones and indenones from simple ortho-allyl benzoic acid derivatives has been developed. Selective formation of the indanone or indenone products in these reactions is controlled by choice of ancillary ligand. This new process has a low environmental footprint as the products are formed in high yields using low catalyst loadings, while the only stoichiometric chemical waste generated from the reactants in the transformation is acetic acid. The conversion of the active cyclization catalyst into the Hermman-Beller palladacycle was exploited in a one-pot tandem acyl Heck-Heck (aHH) reaction, and utilized in the synthesis of donepezil. Carboxylic acids in aHH: Simple ortho-allyl benzoic acid derivatives have been utilized in an acyl Heck (aH) reaction to selectively form indanones and indenones. The conversion of the active cyclization catalyst into the Hermman-Beller palladacycle was exploited in a one-pot tandem acyl Heck-Heck (aHH) reaction to form two sp 2-sp2 bonds of (E)-trisubstituted olefins.

Palladium-catalyzed annulation reactions of methyl o-halobenzoates with azabicyclic alkenes: A general protocol for the construction of benzo[c]phenanthridine derivatives

The annulation reaction of methyl o-halobenzoates with azabicyclic alkenes proceeds efficiently to give the corresponding benzo[c]phenanthridine derivatives in good to excellent yields using a developed base-free methodology based on our preliminary studies. Thirty-seven application examples validate the compatibility of the present strategy with different groups, particularly with the electron-deficient ones, that are difficult to access using other traditional methods. In addition, annulation reactions with non-symmetric azabicyclic alkenes are achieved in high regioselectivity.

Studies on the synthesis and biosynthesis of the fungal alkaloid necatorone

An alternative pathway for the biosynthesis of the fungal alkaloid necatorone has been studied using fluorine-labeled 3-(2-carboxyphenylamino)-l- tyrosine. Although no incorporation of this compound could be detected in feeding experiments with young specimens of Lactarius necator, an analogous 3-aminotyrosine derivative could be converted synthetically into the oxopyridoacridine core structure of necatorone. In experiments aimed at the synthesis of aaptamine-type alkaloids, an unprecedented cyclization of a 3-aminotyrosine-methyl propiolate adduct to a methyl isoquinoline-3-carboxylate was observed. A mechanism is proposed, in which C3 of the propiolate delivers C1 of the isoquinoline nucleus.

INHIBITORS OF STEAROYL-COA DESATURASE

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity.

Condensed pyrazole derivatives, process for producing the same and use thereof

Novel pharmaceutical compositions for inhibiting Th2-selective immune response and pharmaceutical compositions for inhibiting cyclooxygenase comprising condensed pyrazole derivatives represented by the general formula (I): or salts thereof.

Pharmaceutical compositions and method of producing anti-psychotic activity without extrapyramidal symptoms

Tricyclic piperidylidene derivatives administered internally to an animal host, in therapeutically effective amounts, produce antipsychotic activity without extrapyramidal symptoms. Certain of the active ingredients are novel compounds per se.