946513-95-7

Usage

Structure

A derivative of phthalimide

Usage

Starting material in the synthesis of various pharmaceuticals and agrochemicals

Potential

Drug intermediate

Biological properties

Antiviral, antibacterial, and antifungal properties

Physical appearance

White to off-white crystalline powder

Application

Research and development, production of fine chemicals

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 3400-45-1 cyclopentanecarboxylic acid 
• 872-53-7 cyclopentanealdehyde 
• 136918-14-4 phthalimide 

Downstream Products

• 898753-83-8 ethyl 4-(cyclopentyl)-4-oxobutanoate 

Relevant academic research and scientific papers

From Esters to Ketones via a Photoredox-Assisted Reductive Acyl Cross-Coupling Strategy

A method was developed for ketone synthesis via a photoredox-assisted reductive acyl cross-coupling (PARAC) using a nickel/photoredox dual-catalyzed cross-electrophile coupling of two different carboxylic acid esters. A variety of aryl, 1°, 2°, 3°-alkyl 2-pyridyl esters can act as acyl electrophiles while N-(acyloxy)phthalimides (NHPI esters) act as 1°, 2°, 3°-radical precursors. Our PARAC strategy provides an alternative and reliable way to synthesize various sterically congested 3°-3°, 3°-2°, and aryl-3° ketones under mild and highly unified conditions, which have been otherwise difficult to access. The combined experimental and computational studies identified a Ni0/NiI/NiIII pathway for ketone formation.

Electroreductive Cross-Coupling of Trifluoromethyl Alkenes and Redox Active Esters for the Synthesis of Gem-Difluoroalkenes

An electroreductive access to gem-difluoroalkenes has been developed through the decarboxylative/defluorinative coupling of N-hydroxyphtalimides esters and α-trifluoromethyl alkenes. The electrolysis is performed under very simple reaction conditions in a

Visible Light-Driven Decarboxylative Alkylation of Aldehydes via Electron Donor–Acceptor Complexes of Active Esters

There are some synthesis methods from widely available aldehydes to the corresponding ketones, however, they involved in multistep reactions with Grignard’s reagents or transition metal catalysts. In this paper, we have developed photocatalyst-free and visible light-driven decarboxylative alkylation of pyridinaldehydes. The photochemical reactions are initiated via photoinduced single electron transfer from triethylamine to N-hydroxyphthalimide esters in electron donor–acceptor complexes. This photochemical method can achieve to translate 15 pyridinaldehydes and 11 2-quinolinaldehydes to the corresponding ketones. Furthermore, this strategy can also achieve two other transformations, disulfanes to aryl sulfides and a styrene sulfone to the alkyl-substituted alkene.

Photoredox-Catalyzed Oxidative Radical-Polar Crossover Enables the Alkylfluorination of Olefins

The three-component alkylfluorination of olefins via an oxidative radical-polar crossover under visible light-induced photocatalysis is disclosed. A key feature of this reaction is the incorporation of two synthetically meaningful components involving a three-dimensional alkyl group and a fluorine atom using easily preparable N-hydroxyphthalimide esters as the alkyl donors and a low-cost hydrogen fluoride as the fluorine source. Furthermore, a one-step procedure using commercially available carboxylic acids demonstrated the versatility of this new method.

Visible light-induced radical cascade reaction of acryloylbenzamides with N-hydroxyphthalimide esters

An efficient and mild cascade reaction of acryloylbenzamides with N-hydroxyphthalimide (NHPI) esters is disclosed. It goes through radical addition and subsequent cyclization to give 4-alkylated isoquinolinediones in the presence of visible light and phot

Access to functionalized luminescent Pt(ii) complexes by photoredox-catalyzed Minisci alkylation of 6-aryl-2,2′-bipyridines

Photoredox-mediated C-H bond alkylation of 6-aryl-2,2′-bipyridines withN-(acyloxy)phthalimides is reported. The reaction exhibits excellent functional group tolerance, including chiral aliphatic groups. The influence of the incorporatedC6′-alkyl group on

MODULATORS OF HSD17B13 AND METHODS OF USE THEREOF

The disclosure relates to compounds and pharmaceutical compositions capable of modulating the hydroxysteroid 17-beta dehydrogenase (HSD17B) family member proteins including inhibiting the HSD17B member proteins, e.g. HSD17B13. The disclosure further relates to methods of treating liver diseases, disorders, or conditions with the compounds and pharmaceutical compositions disclosed herein, in which the HSD17B family member protein plays a role.

Phosphoric Acid Mediated Light-Induced Minisci C?H Alkylation of N-Heteroarenes

Herein, we report an environmentally-friendly light-induced Minisci alkylation of N-heteroarenes with a broad substrate scope using diphenyl phosphate as catalyst under metal- and photocatalyst-free conditions. The radical precursor redox-active esters (R

Synthesis of 2-alkyl-chroman-4-onesviacascade alkylation-dechlorination of 3-chlorochromones

An efficient and mild synthetic approach for 2-alkyl-substituted chroman-4-onesviazinc-mediated cascade decarboxylative β-alkylation and dechlorination of 3-chlorochromones was developed. This transformation employed commercially available starting materials and was performed under mild conditions without heat, visible light, peroxide or heavy metals. Moreover, various alkyl NHPI esters with functional groups and differently substituted 3-chlorochromones were tolerated, affording the targeted products with moderate to excellent yields. This protocol could be utilized to construct a diverse library of 2-substituted chroman-4-one derivatives, which could be useful in the discovery of lead compounds for drug discovery in the future.

Biocompatible Photoinduced Alkylation of Dehydroalanine for the Synthesis of Unnatural α-Amino Acids

A site-selective alkylation of dehydroalanine to access protected unnatural amino acids is described. The protocol is characterized by the wide nature of alkyl radicals employed, mild conditions, and functional group compatibility. This protocol is further extended to access peptides, late-stage functionalization of pharmaceuticals, and enantioenriched amino acids.