4583-50-0

Usage

Uses

Used in Organic Synthesis:
N-Benzoylphthalimide is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, making it a valuable component in the creation of new organic compounds.
Used in Pharmaceutical Production:
N-Benzoylphthalimide is used as an intermediate in the production of various pharmaceuticals, contributing to the development of new medications and therapies.
Used in Agrochemical Production:
N-Benzoylphthalimide is also utilized as an intermediate in the production of agrochemicals, playing a role in the creation of products that support agricultural processes.
Used in Polymerization Process:
N-Benzoylphthalimide is used as a photoinitiator in the polymerization process, facilitating the formation of polymers through exposure to light.
Used in Oxidation Inhibition:
N-Benzoylphthalimide is used as an inhibitor in the oxidation of organic compounds, helping to prevent or slow down the oxidation process in various applications.

InChI:InChI=1/C15H9NO3/c17-13(10-6-2-1-3-7-10)16-14(18)11-8-4-5-9-12(11)15(16)19/h1-9H

Upstream product

• 110-86-1 pyridine 
• 136918-14-4 phthalimide 
• 98-88-4 benzoyl chloride 
• 100-52-7 benzaldehyde 
• 582-25-2 Potassium benzoate 
• 80824-98-2 diphenyl (1,3-dioxoisoindolin-2-yl)phosphonate 
• 85-44-9 phthalic anhydride 
• 39536-32-8 sodium benzamidate 
• 71-43-2 benzene 
• 93-97-0 benzoic acid anhydride 
• 1074-82-4 potassium phtalimide 
• 65-85-0 benzoic acid 

Downstream Products

• 76-84-6 triphenylmethyl alcohol 
• 6637-53-2 3-hydroxy-3-phenyl-2,3-dihydro-isoindol-1-one 
• 884-09-3 phenyl thiobenzoate 
• 10371-42-3 S-(4-methylphenyl) thiobenzoate 
• 4906-35-8 S-(4-chlorophenyl) benzothioate 
• 119-61-9 benzophenone 
• 613-37-6 4-methoxylbiphenyl 
• 712-50-5 Cyclohexyl phenyl ketone 
• 134-84-9 4-Methylbenzophenone 
• 1934-92-5 N-methyl-N-phenyl-benzamide 
• 2005-08-5 4-chlorophenyl benzoate 
• 54346-96-2 2-(2-benzoxazolyl)-1H-isoindole-1,3(2H)-dione 
• 67958-98-9 2-benzoyl-1',8'-dihydroxy-spiro[isoindole-1,9'-xanthen]-3-one 
• 67958-99-0 2-benzoyl-3',6'-dihydroxy-spiro[isoindole-1,9'-xanthen]-3-one 

Relevant academic research and scientific papers

Development of succinimide-based inhibitors for the mitochondrial rhomboid protease PARL

While the biochemistry of rhomboid proteases has been extensively studied since their discovery two decades ago, efforts to define the physiological roles of these enzymes are ongoing and would benefit from chemical probes that can be used to manipulate the functions of these proteins in their native settings. Here, we describe the use of activity-based protein profiling (ABPP) technology to conduct a targeted screen for small-molecule inhibitors of the mitochondrial rhomboid protease PARL, which plays a critical role in regulating mitophagy and cell death. We synthesized a series of succinimide-containing sulfonyl esters and sulfonamides and discovered that these compounds serve as inhibitors of PARL with the most potent sulfonamides having submicromolar affinity for the enzyme. A counterscreen against the bacterial rhomboid protease GlpG demonstrates that several of these compounds display selectivity for PARL over GlpG by as much as two orders of magnitude. Both the sulfonyl ester and sulfonamide scaffolds exhibit reversible binding and are able to engage PARL in mammalian cells. Collectively, our findings provide encouraging precedent for the development of PARL-selective inhibitors and establish N-[(arylsulfonyl)oxy]succinimides and N-arylsulfonylsuccinimides as new molecular scaffolds for inhibiting members of the rhomboid protease family.

Evaluation of Cyclic Amides as Activating Groups in N-C Bond Cross-Coupling: Discovery of N-Acyl-δ-valerolactams as Effective Twisted Amide Precursors for Cross-Coupling Reactions

The development of efficient methods for facilitating N-C(O) bond activation in amides is an important objective in organic synthesis that permits the manipulation of the traditionally unreactive amide bonds. Herein, we report a comparative evaluation of a series of cyclic amides as activating groups in amide N-C(O) bond cross-coupling. Evaluation of N-acyl-imides, N-acyl-lactams, and N-acyl-oxazolidinones bearing five- and six-membered rings using Pd(II)-NHC and Pd-phosphine systems reveals the relative reactivity order of N-activating groups in Suzuki-Miyaura cross-coupling. The reactivity of activated phenolic esters and thioesters is evaluated for comparison in O-C(O) and S-C(O) cross-coupling under the same reaction conditions. Most notably, the study reveals N-acyl-δ-valerolactams as a highly effective class of mono-N-acyl-activated amide precursors in cross-coupling. The X-ray structure of the model N-acyl-δ-valerolactam is characterized by an additive Winkler-Dunitz distortion parameter ?(τ+χN) of 54.0°, placing this amide in a medium distortion range of twisted amides. Computational studies provide insight into the structural and energetic parameters of the amide bond, including amidic resonance, N/O-protonation aptitude, and the rotational barrier around the N-C(O) axis. This class of N-acyl-lactams will be a valuable addition to the growing portfolio of amide electrophiles for cross-coupling reactions by acyl-metal intermediates.

Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)–H Acylation Enabled by Metallaphotoredox Catalysis

The utilizations of omnipresent, thermodynamically stable amides and aliphatic C(sp3)?H bonds for various functionalizations are ongoing challenges in catalysis. In particular, the direct coupling between the two functional groups has not been realized. Here, we report the synergistic activation of the two challenging bonds, the amide C?N and unactivated aliphatic C(sp3)?H, via metallaphotoredox catalysis to directly acylate aliphatic C?H bonds utilizing amides as stable and readily accessible acyl surrogates. N-acylsuccinimides served as efficient acyl reagents for the streamlined synthesis of synthetically useful ketones from simple C(sp3)?H substrates. Detailed mechanistic investigations using both computational and experimental mechanistic studies were performed to construct a detailed and complete catalytic cycle. The origin of the superior reactivity of the N-acylsuccinimides over other more reactive acyl sources such as acyl chlorides was found to be an uncommon reaction pathway which commences with C?H activation prior to oxidative addition of the acyl substrate.

Palladium(II)/N-heterocyclic carbene-catalyzed direct C-H acylation of heteroarenes with N-acylsaccharins

N-Acylsaccharin represents a facile acyl group transfer agent to heteroarenes in the presence of Pd(II)/NHC complexes appended with a pyrene unit. Catalytic acylation of heteroarenes was enhanced by the noncovalent interaction between the pyrene unit and

Synthesis of N,O-acetals by net amide C[sbnd]N bond insertion of aldehydes into N-acyl phthalimides and N-acyl azoles

We found that N-acyl phthalimides and several N-acylated azoles are capable of reacting with aldehydes to form O-acyl-N,O-acetals in an apparent amide C[sbnd]N bond insertion. In the context of N-acyl phthalimides, the reaction is mediated by substoichiometric amounts of sodium iodide and potassium phthalimide. DFT computations supported a proposed mechanism and provided insights into the effect of the alkali metal additive. This strategy could be used to prepare a myriad of N,O-acetals from a range of aldehydes. A one-pot procedure was also developed in which N-acyl phthalimide was generated in situ prior to forming the N,O-acetal product. The one-pot strategy was used to demonstrate that activated amides derived from imidazole, pyrazole, (benzo)triazole, and tetrazole are also amenable substrates. Collectively, these studies provide an approach to the synthesis of a variety of N,O-acetals under mild conditions from inexpensive starting materials.

KF/Al2O3 catalysed synthesis of thiol esters from N-acylphthalimides and thiols

A new method for the preparation of thiol esters from N-acylphthalimides and thiols in the presence of KF/Al2O3 is introduced.

REAGENTS AND SYNTHETIC METHODS. 29. N-ACYLPHTHALIMIDES FROM CARBOXYLIC ACIDS AND PHOSPHOROUS REAGENTS UNDER PHASE TRANSFER CONDITIONS

N-acylphthalimides are obtained from carboxylic acids and potassium phthalimide by means of phenyl dichlorophosphoridate or diphenylphosphorophthalimide under phase transfer conditions.

Process for N-aroylimides

A process for making an N-aroyl derivative of an aromatic imide which comprises reacting an aromatic o-dicarboxylic acid anhydride with a nitrile at a temperature of at least about 250° C and in the presence of a labile proton source.