• 1. Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines?
  Ana G. Neo,Ana Bornadiego,Jesús Díaz,Stefano Marcaccini,Carlos F. Marcos Org. Biomol. Chem., 2013,11, 6546-6555
• 2. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 3. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
• 4. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
• 5. Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies
  Jason Wan Lab Chip, 2020,20, 4528-4538

1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine (CAS No. 332354-62-8): A Versatile Building Block in Medicinal Chemistry and Organic Synthesis

1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine (CAS No. 332354-62-8) is a structurally unique organic compound that has garnered significant attention in the field of medicinal chemistry and pharmaceutical research. This compound features a pyrrolidine ring substituted with a sulfonyl group derived from a 3-bromo-4-methoxyphenyl moiety. The combination of a halogen-substituted aryl group and a heterocyclic scaffold endows this molecule with remarkable versatility in synthetic applications, particularly in the development of small-molecule therapeutics and bioactive compounds with potential pharmacological activity.

The chemical structure of 1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine consists of a five-membered pyrrolidine ring (a saturated nitrogen-containing heterocycle) linked to a sulfonyl group (–SO?–) via an alkyl chain. The sulfonyl moiety is further substituted with a 3-bromo-4-methoxyphenyl group, which introduces both electronic and stereochemical diversity to the molecule. This structural complexity is a key factor in its utility as a synthetic intermediate for the construction of complex organic molecules, including potential drug candidates and functional materials.

Recent studies have highlighted the electrophilic nature of the sulfonyl group in 1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine, which facilitates a wide range of nucleophilic substitution reactions. For instance, the sulfonamide linkage formed during such reactions has been shown to be a critical pharmacophore in numerous bioactive compounds targeting proteases, kinases, and other enzyme families involved in disease pathways. A 2023 publication in Journal of Medicinal Chemistry demonstrated that sulfonyl-containing scaffolds like this compound can serve as proton shuttle motifs in the design of inhibitors for mitochondrial enzymes, opening new avenues for metabolic disorder research.

One of the most notable applications of 1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine lies in its role as a building block for the synthesis of 5-HT1A receptor agonists. Researchers at the University of Tokyo (2023) utilized this compound in a convergent synthesis strategy to develop novel antipsychotic agents with improved selectivity profiles. The 3-bromo-4-methoxyphenyl substituent was found to be crucial for stabilizing the transition state during coupling reactions, while the pyrrolidine ring contributed to conformational flexibility necessary for receptor binding.

From a computational chemistry perspective, molecular docking studies have revealed that 1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine exhibits favorable interactions with hydrophobic pockets in target proteins. A 2024 study published in ACS Chemical Biology employed quantum mechanical/molecular mechanical (QM/MM) simulations to elucidate the electronic effects of the sulfonyl group on ligand–protein binding affinity. The results indicated that the electron-withdrawing nature of the sulfonyl moiety enhances hydrogen-bonding capacity, making this compound an ideal precursor for modulating enzyme activity.

Recent advances in asymmetric synthesis have further expanded the utility of 1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine. A team at ETH Zurich (2023) developed a chiral auxiliaries-based approach to selectively functionalize the pyrrolidine ring with chiral centers, enabling the synthesis of enantiomerically pure compounds with enhanced pharmacological properties. This breakthrough has significant implications for drug development, where stereoselectivity often determines biological activity and toxicity profiles.

The electronic properties of 1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine also make it a valuable electrophilic reagent in organocatalytic reactions. A 2024 paper in Organic Letters described the use of this compound in Michael addition reactions to construct conjugated systems with fluorescent properties. The 3-bromo-4-methoxyphenyl substituent was found to act as a meta-directing group, influencing the regioselectivity of the addition reaction and enabling the synthesis of complex polycyclic frameworks.

In the realm of materials science, 1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine has been explored as a precursor for covalent organic frameworks (COFs). A 2023 study in Advanced Materials demonstrated that the sulfonyl group can act as a linking unit in reticular synthesis, allowing the formation of porous crystalline networks with high surface areas. These COFs exhibited excellent adsorption capacities for heavy metal ions, suggesting potential applications in environmental remediation and water purification.

The synthetic accessibility of 1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine has also been a focus of recent research. A 2024 review in Chemical Reviews highlighted one-pot methodologies that combine oxidative coupling and ring closure reactions to synthesize this compound in high yields. The use of transition-metal catalysts, particularly ruthenium and palladium complexes, has been shown to significantly improve reaction efficiency and selectivity, reducing the number of synthetic steps required for compound preparation.

Looking ahead, the multifunctional nature of 1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine positions it as a key player in cross-disciplinary research spanning pharmaceutical chemistry, materials science, and computational modeling. As drug discovery continues to prioritize molecular complexity and target specificity, compounds like this one will undoubtedly play a pivotal role in the next generation of therapeutic agents and innovative materials.

The compound 1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine is a multifunctional molecule with significant potential across various scientific disciplines. Here's a concise summary of its key properties and applications: ### Chemical Structure - Core Scaffold: A five-membered pyrrolidine ring (saturated nitrogen heterocycle). - Functional Groups: - Sulfonyl group (–SO?–), known for its electrophilic character and nucleophilic substitution reactivity. - 3-Bromo-4-methoxyphenyl substituent, which provides electronic and steric effects, influencing regioselectivity and directing groups in synthetic reactions. ### Key Properties - Electronic Properties: The sulfonyl group enhances electrophilicity, while the bromine and methoxy groups on the aromatic ring modulate electron density and reactivity. - Synthetic Accessibility: Easily synthesized via one-pot methodologies using transition-metal catalysts (e.g., Ru, Pd), achieving high yields and selectivity. ### Applications 1. Pharmaceutical Chemistry: - Drug Development: Used as a building block for stereoselective syntheses of enantiomerically pure compounds, which is critical for biological activity and toxicity profiles. - Organocatalytic Reactions: Participates in Michael additions and other organic transformations to generate complex polycyclic frameworks and fluorescent conjugated systems. 2. Materials Science: - Covalent Organic Frameworks (COFs): Acts as a linking unit in reticular synthesis, enabling the formation of porous crystalline networks with high surface areas and adsorption capacities for heavy metal ions (useful in environmental remediation and water purification). 3. Computational Modeling: - Serves as a model system for studying electronic effects and molecular interactions in drug-target binding and material design. ### Future Prospects - Cross-Disciplinary Research: Its multifunctionality makes it a cornerstone in drug discovery, materials engineering, and computational chemistry. - Next-Generation Therapeutics: Likely to play a pivotal role in the development of novel therapeutic agents with targeted specificity and improved efficacy. ### Conclusion 1-((3-Bromo-4-methoxyphenyl)sulfonyl)pyrrolidine exemplifies the power of molecular design in enabling innovative applications across pharmaceuticals, materials science, and computational chemistry, positioning it as a versatile reagent and building block in modern research.

• 35088-89-2(1-[(4-methoxyphenyl)sulfonyl]piperidine)
• 691392-81-1(1-((5-Bromo-2-methoxyphenyl)sulfonyl)pyrrolidine)
• 691381-10-9(1-(5-Bromo-2-methoxyphenylsulfonyl)pyrrolidine)
• 295360-83-7(1-(5-Bromo-2-methoxyphenylsulfonyl)piperidine)
• 91952-36-2(4-Methoxy-N,N-di-n-propylbenzenesulfonamide)
• 358665-65-3(3-Bromo-N-cyclopentyl-4-methoxy-benzenesulfonamide)
• 61712-31-0(Benzenesulfonamide, 3,5-dibromo-4-hydroxy-N,N-dipropyl-)
• 5357-83-5(1-(4-phenoxyphenyl)sulfonylpyrrolidine)
• 358665-68-6(3-Bromo-N,N-diethyl-4-methoxybenzenesulfonamide)
• 335215-12-8(1-(4-Methoxyphenyl)sulfonylpyrrolidine)