1255928-86-9

Basic information

• Product Name: (S)-2-(1-(4-chlorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal
• Synonyms: (S)-2-(1-(4-chlorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal
• CAS NO: 1255928-86-9
• Molecular Weight: 279.723
• Mol File: 1255928-86-9.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-(1-(4-chlorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(1-(4-chlorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal(1255928-86-9)
• EPA Substance Registry System: (S)-2-(1-(4-chlorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal(1255928-86-9)

Safety Data

• Hazardous Substances Data: 1255928-86-9(Hazardous Substances Data)

Upstream product

• 1631-29-4 N-(4-chlorophenyl)maleimide 
• 78-84-2 isobutyraldehyde 

Relevant articles and documents

Solvent-induced reversal of enantioselectivity in the synthesis of succinimides by the addition of aldehydes to maleimides catalysed by carbamate-monoprotected 1,2-diamines

A simple change in the polarity of the solvent allows both enantiomers of substituted succinimides to be obtained in the enantioselective conjugate addition reaction of aldehydes, mainly disubstituted, to maleimides catalysed by chiral carbamate-monoprote

α-Amino Acids and α,β-Dipeptides Intercalated into Hydrotalcite: Efficient Catalysts in the Asymmetric Michael Addition Reaction of Aldehydes to N-Substituted Maleimides

In this work, a series of α-amino acids (L-Phe, D-Phe, L-Trp) and several α,β-dipeptides (H2N-L-Val-N-Bn-β-Ala-COOH and H2N-L-Leu-N-Bn-β-Ala-COOH) intercalated into hydrotalcite (Mg/Al, x=0.333) were prepared by high speed ball milling (HSBM) assisted rehydration/reconstruction methods, followed by sonication and mechanical stirring. All organic-inorganic hybrid samples were characterized by powder X-ray diffraction (XRD) and FTIR-ATR spectroscopy. The catalytic activity of the resulting hydrotalcite-supported materials (natural and hybrid) was evaluated in the asymmetric Michael addition reaction of α,α-disubstituted-aldehydes to N-substituted-maleimides. Pristine (HTS), calcined (HTC) and water-reconstructed (HTR-l) hydrotalcite-derived materials exhibited very low catalytic activities, affording racemic mixtures of the anticipated Michael adduct. By contrast, hybrid materials showed better activities, especially HTR-α-amino acid catalysts afforded Michael products in up to 94 % yield and with rather high enantioselectivity (enantiomeric ratio (e.r.) up to 99 : 1) at room temperature under neat reaction conditions. The effect of solvents and Br?nsted basic or acidic additives was evaluated using the best hybrid catalyst, HTR-L-Phe. In addition, recycling and reuse of the catalyst (up to 4 cycles) and large-scale experiments was successfully carried out.

N-Primary-amine tetrapeptide-catalyzed highly asymmetric Michael addition of aliphatic aldehydes to maleimides

The highly asymmetric Michael addition reaction between maleimides and aliphatic aldehydes catalyzed by low-loading β-turn tetrapeptides with excellent yields and enantioselectivities at room temperature was reported. α-Branched and α-unbranched aldehydes both are suitable nucleophiles. N-Aryl, alkyl and hydrogen maleimides all are well tolerated and led to high yields and enantioselectivities. The transformation can be enlarged to the gram scale without decrease in the yield and enantioselectivity. Furthermore, the succinimides were converted into γ-lactams and γ-lactones, showing good practicality of this work. Some reaction intermediates in the proposed reaction mechanism can be captured with the HR-MS method.

Dendrimeric α,β-dipeptidic conjugates as organocatalysts in the asymmetric Michael addition reaction of isobutyraldehyde to N-phenylmaleimides

Abstract: A series of polyester dendrimers (1G to 3G generation) based on 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoic acid (bis-MPA) and the core of 1,3-propanediol-2-(hydroxymethyl)-2-methyl (TME) were synthesized and conjugated to the α,β-dipeptide (N

Enantioselective michael addition of aldehydes to maleimides organocatalyzed by a chiral primary amine-salicylamide

A primary amine-salicylamide derived from chiral trans-cyclohexane-1,2-diamine was used as an organocatalyst for the enantioselective conjugate addition of aldehydes, mainly α,α-disubstituted to N-substituted maleimides. The reaction was performed in tolu

Organocatalytic enantioselective conjugate addition of aldehydes to maleimides in deep eutectic solvents

The conjugate enantioselective addition of aldehydes, mainly α,α-disubstituted, to maleimides leading to enantioenriched succinimides, has been achieved in recyclable deep eutectic solvents at room temperature. Enantiomerically pure carbamate-monoprotecte

Asymmetric Michael addition organocatalyzed by α,β-dipeptides under solvent-free reaction conditions

The application of six novel α,β-dipeptides as chiral organocatalysts in the asymmetric Michael addition reaction between enolizable aldehydes and N-arylmaleimides or nitroolefins is described. With N-arylmaleimides as substrates, the best results were achieved with dipeptide 2 as a catalyst in the presence of aq. NaOH. Whereas dipeptides 4 and 6 in conjunction with 4-dimethylaminopyridine (DMAP) and thiourea as a hydrogen bond donor proved to be highly efficient organocatalytic systems in the enantioselective reaction between isobutyraldehyde and various nitroolefins.

Highly enantioselective Michael addition of α,α-disubstituted aldehydes to maleimides catalyzed by new primary amine-squaramide bifunctional organocatalysts

New bifunctional primary amine-squaramides catalyzed asymmetric Michael addition reaction of α,α-disubstituted aldehydes to maleimides has been developed. This organocatalytic asymmetric reaction provides easy access to functionalized succinimides with a

Primary Amine-2-Aminopyrimidine Chiral Organocatalysts for the Enantioselective Conjugate Addition of Branched Aldehydes to Maleimides

Chiral primary amines containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a pyrimidin-2-yl unit are synthesized and used as general organocatalysts for the Michael reaction of α-branched aldehydes to maleimides. The reaction takes place with 10 mol% organocatalyst loading and hexanedioic acid as cocatalyst in aqueous N,N-dimethylformamide at 10 °C affording the corresponding succinimides in good yields and enantioselectivities. DFT calculations support the stereochemical results and the role played by the solvents.

Solvent-dependent enantioswitching in the Michael addition of α,α-disubstituted aldehydes to maleimides organocatalyzed by mono-N-Boc-protected cyclohexa-1,2-diamines

Enantiomerically pure mono-N-Boc-protected trans-cyclohexa-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to maleimides. Using a single enantiomer of the organocatalyst, both enantiomeri