139477-41-1

Usage

Appearance

White to off-white crystalline solid

Usage

Precursor in the synthesis of pharmaceuticals and other organic compounds

Medicinal properties

Potential anti-inflammatory and analgesic agent

Applications

Building block in the production of agrochemicals, dyes, and other specialty chemicals

Importance

Various fields of organic chemistry

Potential applications

Pharmaceutical and chemical industries

InChI:InChI=1/C16H19NO2/c18-15-11-14(12-7-3-1-4-8-12)16(19)17(15)13-9-5-2-6-10-13/h1,3-4,7-8,13-14H,2,5-6,9-11H2

Upstream product

• 635-51-8 2-phenylsuccinic acid 
• 108-91-8 cyclohexylamine 
• 1233241-12-7 C₁₇H₂₃NO₃ 
• 1631-25-0 N-cyclohexylmaleimide 
• 98-80-6 phenylboronic acid 
• 16213-23-3 2-phenyl-N-cyclohexylmaleimide 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 

Relevant academic research and scientific papers

Highly Enantioselective Synthesis of Chiral Succinimides via Rh/Bisphosphine-Thiourea-Catalyzed Asymmetric Hydrogenation

We have successfully developed a highly enantioselective hydrogenation of various 3-aryl and 3-methyl maleinimides to access enantiomerically pure 3-substituted succinimides catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos). This efficient catalytic system furnished the desired 3-substituted succinimide products with high yields and enantioselectivities (up to 99% yield, full conversions, almost all 3-aryl succinimide products up to 99% ee, and 3-methyl succinimide with 83% ee). Our catalytic system has a strong substrate tolerance and generality. Whether the N-substituted group of maleinimides is H or other protecting groups, the maleinimides were hydrogenated well (up to >99% ee, 99% yield). Moreover, the hydrogenation succinimide products can be readily utilized for the construction of biologically active molecules, such as chiral amides and pyrrolidines.

Direct Synthesis of Chiral 3-Arylsuccinimides by Rhodium-Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids to Maleimides

Chiral rhodium catalysts comprising 2,5-diaryl- substituted bicyclo[2.2.1]diene ligands L1-L10 were utilized in the enantioselective 1,4-addition reaction of arylboronic acids to N-substituted maleimides. In the presence of 2.5mol % of RhI/L2, enantioenriched conjugate addition adducts were isolated in 72-99 % yields with 86-98 %ee. This protocol offers a convenient method to access a variety of 3-arylsuccinimides in a highly enantioselective manner. Maleimides with readily cleavable N-protecting groups were tolerated enabling the synthesis of useful synthetic intermediates. Pyrrolidine 4, a biologically active compound, and pyrrolidine 5, an ent-precursor to an HSD-1 inhibitor, were synthesized to demonstrate the utility of this method. The road to rhodium! Enantioselective conjugate addition of a range of arylboronic acids to variously N-substituted maleimides, catalyzed by RhI complexes prepared in situ using chiral bicyclo[2.2.1]diene ligands, afforded the corresponding 3-arylsuccinimides with up to 98 %ee at 50 C (see scheme).

Low-temperature Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds

Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds was achieved at temperatures below 0 C using a Rh/MeO-F12-BIPHEP catalyst. The reaction of cyclohexenone or N-R-maleimide with arylboronic acids proceeded even at -80 C in the presence of the Rh catalyst. In the latter case, high enantioselectivity was observed because a low-temperature method was used, regardless of the type of substituent on maleimide.

Room-temperature Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to maleimides and enones in the presence of CF3-substituted MeOBIPHEP analogues

A Rh-based catalytic system implying electron-poor MeOBIPHEP analogues has been developed for the 1,4-addition of boronic acids to maleimides and enones under mild conditions at room temperature and led to succinimide derivatives and arylated cyclic ketones in good to excellent yields and ee. We uncovered the crucial role of the electronic and steric properties of diphosphine ligand and observed a strong boronic acid/ligand dependency in the case of maleimide derivatives and substrate/ligand matching in the case of cyclic enones.

Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones with DIFLUORPHOS and SYNPHOS analogues

Applications of electron-deficient DIFLUORPHOS and SYNPHOS analogues in the rhodium-catalyzed asymmetric conjugate addition of boronic acids to α,β-unsaturated ketones afford the 1,4-addition adducts in yields up to 92% and with 99% ee. Particularly, a Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to nonsubstituted maleimide substrates using the (R)-3,5-diCF3-SYNPHOS ligand is also reported. This protocol provides access to various enantioenriched 3-substituted succinimide units of biological interest, in high yields and good to excellent ee up to 93%, which could be upgraded up to 99% ee, after a single crystallization.

A general and selective iron-catalyzed aminocarbonylation of alkynes: Synthesis of acryl- and cinnamides

Entering the iron age: The first general method for iron-catalyzed monocarbonylation of alkynes has been developed. A range of structurally diverse cinnamides and acrylamides have been obtained smoothly starting from commercially available amines and alkynes in the presence of [Fe 3(CO)12] and ligand L (see scheme). The method is highly chemo- and regioselective and requires no expensive catalyst.

Palladium-catalyzed selective alkoxycarbonylation of α,β-unsaturated amides: a novel approach toward new ω-amido esters and N-substituted cyclic succinimides

The alkoxycarbonylation of α,β-unsaturated amides proceeded efficiently and regioselectivity to give ω-amido esters with complete conversion in the presence of the catalyst system: Pd(PPh3)2Cl2/MeOH/CO/H2O. The reaction was successfully applied to the alkoxycarbonylation of bis-acrylamides yielding, selectively, the corresponding di-ω-amido esters. These mono and di-ω-amido esters have been used as precursors for the synthesis of N-substituted cyclic succinimides in moderate to high yields.

Chiral phosphine-olefin bidentate ligands in asymmetric catalysis: Rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to maleimides

(Chemical Equation Presented) Two is better than one: Novel chiral phosphine - olefin ligands 1 a and 1 b act as bidentate ligands with some transition metals and have proved to be highly effective in the rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to maleimides with high enantio-selectivity (see scheme).

Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds

(Chemical Equation Presented) A rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds has been developed. While phosphorus-based chiral ligands fail to induce high stereoselectivity, chiral norbornadiene ligands have proved to be uniquely effective to achieve high enantioselectivity in these 1,4-addition reactions.

Some new N-substituted α-aryl/alkyl succinimides as possible anticonvulsants

In view of their expected MAO inhibitory CNS depressant and anticonvulsant properties a number of N-(5-alkyl-1,3,4-thiadiazol-2-yl)-α-aryl/alkyl succinimides (1-20) and N-(cyclohexyl)-α-aryl/alkyl succinimides (21-25) have been synthesized. Some of them when screened for anticonvulsant activity against pentetrazole induced seizures in mice at a dose of 80 mg/kg were found to be 10 to 50% active.