89736-77-6

Usage

Chemical group

Pyrrolidine-2,5-dione derivatives

Common uses

Surfactant and emulsifier in cosmetics, personal care products, and pharmaceuticals

Benefits

Improves stability and solubility of substances in formulations, enhances texture and feel of products when applied to the skin

Versatility

Widely used in the manufacturing of various products for different industries.

InChI:InChI=1/C12H21NO2/c1-2-3-4-5-6-7-10-13-11(14)8-9-12(13)15/h2-10H2,1H3

Upstream product

• 111-86-4 n-Octylamine 
• 110-15-6 succinic acid 
• 128-09-6 N-chloro-succinimide 
• 112-05-0 nonanoic acid 
• 516-12-1 N-iodo-succinimide 
• 108-30-5 succinic acid anhydride 
• 89736-73-2 N-(2-chloro-1-octyl)succinimide 

Relevant academic research and scientific papers

ESTER COMPOUND, GELLING AGENT, AND COMPOSITION

PROBLEM TO BE SOLVED: To provide a novel low molecular weight compound, a gelling agent and a composition that are excellent in gell recoverability and capability of gelling to an oil gel. SOLUTION: An ester compound is represented by one of the general formulas (1), (2) and (3). (In the general formulas (1), (2) and (3), R1 and R4 are each an alkyl group or the like; and R2 and R3 are each an alkylene group or the like.) SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2021,JPO&INPIT

Direct Synthesis of Cyclic Imides from Carboxylic Anhydrides and Amines by Nb2O5 as a Water-Tolerant Lewis Acid Catalyst

In the 20 types of heterogeneous and homogenous catalysts screened, Nb2O5 showed the highest activity for the synthesis of N-phenylsuccinimide by dehydrative condensation of succinic anhydride and aniline. Nb2O5 was used in the direct imidation of a wide range of carboxylic anhydrides with NH3 or amines with various functional groups and could be reused. Kinetic studies showed that the Lewis acid Nb2O5 catalyst was more water tolerant than both the Lewis acidic oxide TiO2 and the homogeneous Lewis acid ZrCl4, which resulted in higher yields of imides through the use of Nb2O5. Int-imidation tactics: A general method for the direct synthesis of cyclic imides from cyclic anhydrides with amines (or ammonia) under solvent-free conditions is reported. Kinetic studies indicate that the Lewis acid sites of Nb2O5 are highly water tolerant, which results in high catalytic activity for imidation even in the presence of water formed during the reaction. The catalyst can be recovered and reused four times without a marked decrease in yield.

One-Pot Transformation of Aliphatic Carboxylic Acids into N-Alkylsuccin-imides with NIS and NCS/NaI

Primary aliphatic carboxylic acids were treated with N-iodosuccinimide (NIS) in 1,2-dichloroethane to form the corresponding alkyl iodides under warming conditions. Based on these results, those aliphatic carboxylic acids were treated with NIS, followed by the reaction with K2CO3to give the corresponding N-alkylsuccinimides in good yields in one pot. Moreover, those aliphatic carboxylic acids were treated with N-chlorosuccinimide (NCS) and NaI, followed by the reaction with K2CO3to provide the corresponding N-alkylsuccinimides in good to moderate yields in one pot. By using the present method, successive treatment of primary aliphatic carboxylic acids (10 mmol) with NIS, K2CO3, and then hydrazine provided the corresponding decarboxylated primary amines in good yield.

Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8-DMSO: Application to the synthesis of vernakalant

Ammonium persulfate-dimethyl sulfoxide (APS-DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.

Versatile and sustainable synthesis of cyclic imides from dicarboxylic acids and amines by Nb2O5 as a base-tolerant heterogeneous lewis acid catalyst

Catalytic condensation of dicarboxylics acid and amines without excess amount of activating reagents is the most atom-efficient but unprecedented synthetic method of cyclic imides. Here we present the first general catalytic method, proceeding selectively and efficiently in the presence of a commercial Nb2O5 as a reusable and base-tolerant heterogeneous Lewis acid catalyst. The method is effective for the direct synthesis of pharmaceutically or industrially important cyclic imides, such as phensuximide, N-hydroxyphthalimide (NHPI), and unsubstituted cyclic imides from dicarboxylic acid or anhydrides with amines, hydroxylamine, or ammonia.

Design, synthesis, and biochemical evaluation of N-substituted maleimides as inhibitors of prostaglandin endoperoxide synthases

N-(Carboxyalkyl)maleimides are rapid as well as time-dependent inhibitors of prostaglandin endoperoxide synthase (PGHS). The corresponding N- alkylmaleimides were only time-dependent inactivators of PGHS, suggesting that the carboxylate is critical for rapid inhibition. Several N-substituted maleimide analogs containing structural features similar to those of the nonsteroidal anti-inflammatory drug aspirin were synthesized and evaluated as inhibitors of PGHS. Most of the aspirin-like maleimides inactivated the cyclooxygenase activity of purified ovine PGHS-1 in a time- and concentration-dependent manner similar to that of aspirin. The peroxidase activity of PGHS was also inactivated by the maleimide analogs. The cyclooxygenase activity of the inducible isozyme, i.e., PGHS-2, was also inhibited by these compounds. The corresponding succinimide analog of N-5- maleimido-2-acetoxy-1-benzoic acid did not inhibit either enzyme activity, suggesting that inactivation was due to covalent modification of the protein. The mechanism of inhibition of PGHS-1 by N-(carboxyheptyl)maleimide was investigated. Incubation of apoPGHS-1 with 2 equiv of N-(carboxyheptyl)[3,4- 14C]maleimide led to the incorporation of radioactivity in the protein, but no adduct was detected by reversed-phase HPLC, suggesting that it was unstable to the chromatographic conditions. Furthermore, hematin- reconstituted PGHS-1, which was rapidly inhibited by N- (carboxyheptyl)maleimide, displayed spontaneous regeneration of about 50% of the cyclooxygenase and peroxidase activities, suggesting that the adduct responsible for the inhibition breaks down to regenerate active enzyme. ApoPGHS-1, inhibited by N-(carboxyheptyl)maleimide, did not display regeneration of enzyme activity, but addition of hematin to the inhibited apoenzyme led to spontaneous recovery of about 50% of cyclooxygenase activity. These results suggest that addition of heme leads to a conformational change in the protein which increases the susceptibility of the adduct toward hydrolytic cleavage. ApoPGHS-1, pretreated with N(carboxyheptyl)maleimide, was resistant to trypsin cleavage, suggesting that the carboxylate functionality of the maleimide binds in the cyclooxygenase channel. A model for the interaction of N-(carboxyheptyl)maleimide in the cyclooxygenase active site is proposed.

The photochemical addition of N-haloamides to olefins: a comparison of cyclic and acyclic N-halo-N-alkylamides and N-halo-N-acylamides (N-haloimides)

Upon photochemical decomposition in the presence of cyclohexene and 1-octene, an N-halo-N-acylamide (N-haloimide) leads to better yields of addition than its N-halo-N-alkyl analogue, and cyclic N-halo-N-alkyl and N-halo-N-acylamides add more efficiently than their acyclic analogues.The yields of addition were higher with N-chlorosuccinimide which has been added also to 1-methylcyclohexene than with N-bromosuccinimide which did not add to 1-methylcyclohexene.