14063-01-5

Usage

Chemical compound

2,5-Pyrrolidinedione, 3-(phenylmethylene)-

Class

Pyrrolidinediones

Molecular weight

199.20 g/mol

Usage

Organic synthesis
Pharmaceutical research

Biological activities

Antioxidant properties
Potential therapeutic applications
Intermediate in the production of other chemicals and pharmaceuticals
Further research needed to explore full range of uses and benefits

Upstream product

• 18092-16-5 triphenylphosphoranylidene succinimide 
• 100-52-7 benzaldehyde 
• 541-59-3 maleiimide 

Downstream Products

• 170304-83-3 3-benzylpyrrolidine 
• 66195-04-8 3-benzyl-pyrrolidine-2,5-dione 

Relevant academic research and scientific papers

A Solid-Phase Assisted Flow Approach to In Situ Wittig-Type Olefination Coupling

Described herein is the development of a continuous flow, solid-phase triphenylphosphine (PS-PPh3) assisted protocol to facilitate the in situ coupling of reciprocal pairs of halogen and carbonyl functionalised molecular pairs by a Wittig olefination within 15 mins. The protocol entails injecting a single solution (1 : 1 CHCl3 : EtOH) containing the halogenated and carbonyl-based substrates into a continuously flowing stream of CHCl3 : EtOH (1 : 1), passed through a fixed bed of K2CO3 and PS-PPh3. With advancement to the previous PS-PPh3 coupling procedures, the method employs a traditional polystyrene-based immobilisation matrix, the substrate scope of the protocol extended to substituted ketones, secondary alkyl chlorides, and an unprotected maleimide scaffold.

Poly(methylhydrosiloxane) as a reductant in the catalytic base-free Wittig reaction

Herein, we report a catalytic, base-free Wittig reaction forming highly functionalized alkenes with PMHS as a terminal reductant and butylacetate as a green solvent. Poly(methylhydrosiloxane) (PMHS) is a non-toxic, enviromentally friendly, inexpensive and easy to handle reductant. However, the inherent low reactivity hampers its applicability in catalytic reactions, such as P(iii)/P(v) redox cycling reactions. Most of these catalytic systems include highly active aryl silanes to facilitate phosphane oxide reduction and are not compatible with PMHS or similar more sustainable terminal reductants. The herein reported catalyst system which is based on a methyl-substituted phosphetane operates at low catalyst loadings without additional co-catalysts and allowes the use of PMHS as terminal reductant. A wide variety of functional groups was tolerated and 25 different alkenes were synthesized in yields up to 96% with excellent stereoselectivity. Mechanistic studies revealed the formation of water from silanol condensation as the main pathway of siloxane formation.

Novel Base-Free Catalytic Wittig Reaction for the Synthesis of Highly Functionalized Alkenes

A highly efficient catalyst system for base-free catalytic Wittig reactions has been developed and optimized. Initially, several potential (pre)catalysts as well as different silanes as reducing agents were screened. A system based on a readily available

The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides

A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides catalyzed by a novel chiral N,O-ligand/Cu(OAc)2 system is reported, affording dispiropyrrolidine derivatives with spiro quaternary stereog

Using T-Hg-T and C-Ag-T: A four-input dual-core molecular logic gate and its new application in cryptography

A simple four-input dual-core (thymine & cytosine) logic gate was successfully developed that utilized a succinic imide labelled pyrene probe as the signal responser. Moreover, this molecular logic gate could be made into fluorescent paper and applied in the field of cryptography.

Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice

A large amount of evidence suggests that monocytes/macrophages infiltration is implicated in a variety of inflammatory diseases including acute liver injury. Monocyte chemoattractant protein 1 (MCP-1) plays a crucial role in the process of macrophages recruitment. We herein presented a small-molecule library and a feasible quick screening method of evaluating potency of inhibition of chemotaxis of RAW264.7 cells stimulated by MCP-1. Fifty-three small molecules were synthesized and screened, and four compounds (2g, 2h, 4f, and 6h) showed inhibitory effects with IC50 values range from 0.72 to 20.47 μM, with compound 4f being the most efficient. Further in vivo studies demonstrated that oral administration of 2g, 2h, 4f, or 6h decreases, most significantly for 4f, the serum levels of alanine aminotransaminase (ALT) and asparate aminotransaminase (AST) in ConA-induced acute livery injury BALB/c mice. Histopathological evaluation liver sections confirmed 4f as a potent, orally active compound for hepatoprotective effects against ConA-induced acute liver injury in BALB/c mice.

4-[ω-(tetralin-1-yl)alkyl]-1-benzylpiperazines and related compounds as 5-HT1A/D-2 ligands

N-Benzylpiperazine and -piperidine derivatives of long-chain piperazine were synthesized in order to obtain putative atypical antipsychotic agents with a dual 5-HT1A/D-2 affinity and reduced, or without, α1 adrenergic affinity. The 5-HT1A/D-2/α1 receptor binding results show that only compound 30, 2-(2-methoxybenzyl)-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-n-propyl] piperazine, has an acceptable binding affinity profile (pKi= 7.9, 7.1, 6.7, respectively).