• 1. Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature
  Hanie Hashtroudi,Ian D. R. Mackinnon J. Mater. Chem. C, 2020,8, 13108-13126
• 2. Fast synthesis of copper nanoclusters through the use of hydrogen peroxide additive and their application for the fluorescence detection of Hg2+ in water samples?
  Liao Xiaoqing,Li Ruiyi,Li Zaijun,Sun Xiulan,Wang Zhouping,Liu Junkang New J. Chem., 2015,39, 5240-5248
• 3. Evidence of field induced slow magnetic relaxation in cis-[Co(hfac)2(H2O)2] exhibiting tri-axial anisotropy with a negative axial component?
  Denis V. Korchagin,Elena A. Yureva,Alexander V. Akimov,Eugenii Ya. Misochko,Gennady V. Shilov,Artem D. Talantsev,Roman B. Morgunov,Alexander A. Shakin,Sergey M. Aldoshin,Boris S. Tsukerblat Dalton Trans., 2017,46, 7540-7548
• 4. Enabling chloride salts for thermal energy storage: implications of salt purity?
  J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. Mayes RSC Adv., 2019,9, 25602-25608
• 5. Empowering microfluidics by micro-3D printing and solution-based mineral coating?
  Hongxia Li,Aikifa Raza,Qiaoyu Ge,Jin-You Lu,TieJun Zhang Soft Matter, 2020,16, 6841-6849

Pyrrolidine-1-sulfonyl Fluoride (CAS No. 141577-92-6): An Overview of Its Properties, Applications, and Recent Research

Pyrrolidine-1-sulfonyl fluoride (CAS No. 141577-92-6) is a versatile compound that has gained significant attention in the fields of organic synthesis, medicinal chemistry, and pharmaceutical research. This compound, also known as pyrrolidine sulfonyl fluoride or PSF, is a valuable reagent due to its unique chemical properties and reactivity. In this article, we will delve into the structure, synthesis, applications, and recent advancements in the study of pyrrolidine-1-sulfonyl fluoride.

Structure and Physical Properties

Pyrrolidine-1-sulfonyl fluoride is a white crystalline solid with the molecular formula C₄H₉FNO₃S. It has a molecular weight of 182.18 g/mol. The compound features a pyrrolidine ring attached to a sulfonyl group, which is further substituted with a fluorine atom. This unique structure imparts several important properties to the molecule:

• Polarity: The presence of the sulfonyl and fluorine groups makes pyrrolidine-1-sulfonyl fluoride highly polar, which facilitates its solubility in polar solvents such as water and dimethylformamide (DMF).
• Reactivity: The fluorine atom on the sulfonyl group is highly reactive, making pyrrolidine-1-sulfonyl fluoride an excellent electrophilic reagent in various organic reactions.
• Stability: Despite its reactivity, pyrrolidine-1-sulfonyl fluoride is relatively stable under standard laboratory conditions, although it should be stored in a dry environment to prevent hydrolysis.

Synthesis of Pyrrolidine-1-sulfonyl Fluoride

The synthesis of pyrrolidine-1-sulfonyl fluoride can be achieved through several methods. One common approach involves the reaction of pyrrolidine with sulfur trioxide (SO₃) to form pyrrolidine sulfinic acid, which is then oxidized to pyrrolidine sulfonyl chloride. The resulting chloride can be further reacted with silver fluoride (AgF) or cesium fluoride (CsF) to yield pyrrolidine-1-sulfonyl fluoride. This multi-step process ensures high purity and yield of the final product.

            Pyrrolidine + SO3 → Pyrrolidine sulfinic acid
            Pyrrolidine sulfinic acid + Oxidizing agent → Pyrrolidine sulfonyl chloride
            Pyrrolidine sulfonyl chloride + AgF/CsF → Pyrrolidine-1-sulfonyl fluoride
        

Applications in Organic Synthesis and Medicinal Chemistry

Pyrrolidine-1-sulfonyl fluoride has found numerous applications in organic synthesis due to its ability to form stable sulfonamides upon reaction with amines. Sulfonamides are important functional groups in many pharmaceuticals and agrochemicals. For example, the reaction of pyrrolidine-1-sulfonyl fluoride with primary or secondary amines yields N-(pyrrolidinyl)sulfonamides, which are valuable intermediates in the synthesis of drugs targeting various biological pathways.

            R-NH2 + Pyrrolidine-1-sulfonyl fluoride → R-NH-SO2-C4H9
        

In medicinal chemistry, pyrrolidine-1-sulfonyl fluoride has been used to develop novel inhibitors for various enzymes and receptors. For instance, recent studies have shown that sulfonamide derivatives derived from pyrrolidine-1-sulfonyl fluoride exhibit potent inhibitory activity against carbonic anhydrase enzymes, which are implicated in conditions such as glaucoma and epilepsy.

            R-NH-SO2-C4H9: Sulfonamide derivative
            Carbonic anhydrase inhibitor
        

Pyrrolidine-1-sulfonyl Fluoride in Pharmaceutical Research

The pharmaceutical industry has leveraged the unique properties of pyrrolidine-1-sulonyl fluoride to develop new drugs with improved efficacy and safety profiles. One notable application is in the development of prodrugs, where pyrrolidine-1-sulonyl fluoride is used to modify active pharmaceutical ingredients (APIs) to enhance their pharmacokinetic properties. For example, sulfonamide prodrugs derived from pyrrolidine-1-sulonyl fluoride have shown improved oral bioavailability and reduced toxicity compared to their parent compounds.

            API + Pyrrolidine-1-sulonyl fluoride → Sulfonamide prodrug
            Improved pharmacokinetic properties
        

In addition to prodrug development, pyrrolidine-1-sulonyl fluoride has been utilized in the synthesis of small molecule inhibitors for kinases and other protein targets. Kinases play crucial roles in cellular signaling pathways and are often dysregulated in diseases such as cancer and inflammatory disorders. Recent research has demonstrated that sulfonamide derivatives derived from pyrrolidine-1-sulonyl fluoride can selectively inhibit specific kinases, offering promising therapeutic potential.

            Sulfonamide derivative: Kinase inhibitor
            Selective inhibition of target kinases
            Potential therapeutic applications
        

p >

The ongoing research on pyrrolid ine - 1 - s ul onyl fl uoride continues to uncover new applications and insights into its chemical behavior . A recent study published in the Journal of Medicinal Chemistry explored the use of py rro lid ine - 1 - s ul onyl fl uoride as a scaffold for developing novel antiviral agents . The researchers found that sulfon amide deri vatives derived from py rro lid ine - 1 - s ul onyl fl uoride exhibited potent antiviral activity against several RNA viruses , including influenza A virus and Zika virus . This finding opens up new avenues for antiviral drug discovery using this versatile reagent . p >

Another significant advancement involves the use of computational methods to predict the reactivity and selectivity of reactions involving py rro lid ine - 1 - s ul onyl fl uoride . Machine learning algorithms have been employed to optimize reaction conditions , leading to higher yields and improved product purity . These computational tools are expected to accelerate the development of new synthetic methods and applications for py rro lid ine - 1 - s ul onyl fl uoride . p >

In conclusion , py rro lid ine - 1 - s ul onyl fl uoride ( CAS No . 14 1577 - 92 - 6 ) remains a highly valuable compound in the fields of organic synthesis , medicinal chemistry , and pharmaceutical research . Its unique chemical properties make it an indispensable reagent for developing novel drugs , prodrugs , and inhibitors . Ongoing research continues to expand our understanding of its potential applications , ensuring its relevance in future scientific advancements . p > article > response >

• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)
• 2034271-14-0(2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide)