58585-84-5

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 65-85-0 benzoic acid 
• 93-97-0 benzoic acid anhydride 
• 98-88-4 benzoyl chloride 
• 3459-80-1 t-butoxymethylbenzene 
• 94-36-0 dibenzoyl peroxide 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 123-91-1 1,4-dioxane 
• 15263-19-1 N-chlorocarbonyloxy-phthalimide 
• 78816-91-8 bis(1,3-dioxoisoindolin-2-yl)carbonate 

Downstream Products

• 118-92-3 anthranilic acid 
• 65-85-0 benzoic acid 
• 1485-70-7 N-benzylbenzamide 
• 2782-40-3 N-butylbenzamide 
• 93-98-1 N-phenyl benzoyl amide 
• 3278-14-6 N-phenethylbenzamide 
• 607-55-6 α-naphthyl benzoate 
• 1871-37-0 2,4,6-trimethylphenyl benzoate 
• 403-84-9 benzoic acid-(3-fluoro-4-methyl-phenyl ester) 
• 1871-36-9 2,6-dimethylphenyl benzoate 
• 2005-08-5 4-chlorophenyl benzoate 
• 2714-93-4 4-fluorophenyl benzoate 
• 54683-91-9 o-chlorophenyl benzoate 
• 367-98-6 benzoic acid 2-fluorophenyl ester 

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.

Visible Light-Driven Efficient Synthesis of Amides from Alcohols using Cu?N?TiO2 Heterogeneous Photocatalyst

Amides were synthesized from alcohols and amines in high yields using an in situ generated active ester of N-hydroxyimide with our developed Cu?N?TiO2 catalyst at room temperature using oxygen as a sole oxidant under visible light. The catalyst can be easily prepared, robust, and recycled four times without a considerable change in catalytic activity. This developed protocol applies to a wide substrate scope and has good functional group tolerance. The application of this amidation reaction has been successfully demonstrated for the synthesis of moclobemide, an antidepressant drug, and an analog of the itopride drug on a gram scale.

tert-Butyl Nitrite as a Twofold Hydrogen Abstractor for Dehydrogenative Coupling of Aldehydes with N-Hydroxyimides

A synthetically practical transition metal/catalyst/halogen-free dehydrogenative coupling of aldehydes with N-hydroxyimides promoted solely by tert-butyl nitrite under mild conditions was developed. tert-Butyl nitrite generates two radicals (tBuO and NO) and thus works as a twofold hydrogen abstractor. A diverse array of N-hydroxyimide esters were prepared from either aliphatic or aromatic aldehydes. Benzoyl-substituted aldehydes such as 2-oxo-2-phenylacetaldehyde are also suitable.

Halide-Accelerated Acyl Fluoride Formation Using Sulfuryl Fluoride

Herein, we report a new one-pot sequential method for SO2F2-mediated nucleophilic acyl substitution reactions starting from carboxylic acids. A mechanistic study revealed that SO2F2-mediated acid activation proceeds via the anhydride, which is then converted to the corresponding acyl fluoride. Tetrabutylammonium chloride or bromide accelerate the formation of acyl fluoride. Optimized halide-accelerated conditions were used to synthesize acyl fluorides in 30-80percent yields, and esters, amides, and thioesters in 72-96percent yields without reoptimization for each nucleophile.

N-Doped Yellow TiO2 Hollow Sphere-Mediated Visible-Light-Driven Efficient Esterification of Alcohol and N-Hydroxyimides to Active Esters

Herein we report a simple synthetic protocol for N-doped yellow TiO2 (N-TiO2) hollow spheres as an efficient visible-light-active photocatalyst using aqueous titanium peroxocarbonate complex (TPCC) solution as precursor and NH4OH. In the developed strategy, the ammonium ion of TPCC and NH4OH acts as nitrogen source and structure-directing agent. The synthesized N-TiO2 hollow spheres are capable of promoting the synthesis of active esters of N-hydroxyimide and alcohol through simultaneous selective oxidation of alcohol to aldehyde followed by cross-dehydrogenative coupling (CDC) under ambient conditions upon irradiation of visible light. It is possible to develop a novel and cost-effective one-pot strategy for the synthesis of important esters and amides on gram scale using the developed strategy. The catalytic activity of N-TiO2 hollow spheres is much superior to that of other reported N-TiO2 samples as well as TiO2 with varying morphology.

A visible light-driven minisci-type reaction with N-hydroxyphthalimide esters

A visible light-promoted protocol for the redox-neutral coupling of N-hydroxyphthalimide esters with different N-heterocyclic compounds is described. The reaction proceeds through an alkyl radical intermediate generated by reductive decarboxylation of N-hydroxyphthalimide esters. In contrast to the original Minisci protocol, polyalkylation can largely be avoided. Mechanistic investigations revealed a radical chain mechanism which in some cases can proceed even if no photocatalyst is added. This valuable and functional group-tolerant reaction produces substituted heterocycles in moderate to excellent yield. The use of inexpensive starting materials and LEDs as the light source are key features of this C–C bond formation.

Method for preparing aliphatic alcohol from aliphatic carboxylic acid through decarboxylation

The invention relates to a method for preparing aliphatic alcohol from aliphatic carboxylic acid through decarboxylation. The method comprises the following steps of converting aliphatic carboxylic acid into aliphatic N-(acyl oxy)phthalimide; then, performing photocatalysis decarboxylation reaction to convert the material into aliphatic N-(oxy)2, 2,6,6-tetramethylpiperidine nitrogen-oxygen free radicals; finally, reducing the materials into aliphatic alcohol. The method provided by the invention has the advantages that good chemical selectivity is realized; the wide and easy-to-obtain materialsources are realized. The defects of harsh reaction conditions and high energy consumption such as high temperature and high pressure of aliphatic carboxylic acid conversion by a conventional heat conversion method are avoided; the reaction process is simple and convenient; the operation is easy; the repeated extraction is avoided; in addition, the additional introduction of high-purity hydrogengas is not needed; the reaction energy consumption and the raw material consumption are greatly reduced; the green and environment-friendly effects are achieved; the environment pollution is small; the wide application prospects are realized.

A photoinduced cross-dehydrogenative-coupling (CDC) reaction between aldehydes and N-hydroxyimides by a TiO2-Co ascorbic acid nanohybrid under visible light irradiation

In this study, we performed a visible light-mediated aerobic photo-cross dehydrogenative coupling (CDC) reaction between aldehydes and N-hydroxyimides using TiO2-AA-Co as a photocatalyst for the synthesis of active esters. The synergistic and selective effects of the cobalt ascorbic acid complex (Co-AA) and TiO2 nanoparticles on the visible-light photocatalytic activity were explored. The method possesses some advantages such as environmentally friendly conditions, easy work-up procedure, reusability, and scalability.

Copper nitrate-catalyzed oxidative coupling of unactivated C(sp3)-H bonds of ethers and alkanes with: N -hydroxyphthalimide: Synthesis of N -hydroxyimide esters

A copper nitrate-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) and ethers/alkanes has been described. The reaction is accomplished smoothly by using simple and green molecular oxygen as the oxidant, providing an alternative for the efficient synthesis of N-alkoxyphthalimides. In addition, it was found that when tert-butyl ethers were used as substrates, unexpected N-hydroxyimide ester derivatives were obtained in moderate to excellent yields. To further understand this unusual transformation, control experiments were performed and a plausible mechanism was proposed.