677-25-8Relevant academic research and scientific papers
Ethenesulfonyl Fluoride (ESF): An On-Water Procedure for the Kilogram-Scale Preparation
Zheng, Qinheng,Dong, Jiajia,Sharpless, K. Barry
, p. 11360 - 11362 (2016)
A two-step, on-water procedure for the synthesis of ethenesulfonyl fluoride (ESF) is described. 2-Chloroethanesulfonyl fluoride is made via a neat reaction with an aqueous, nearly saturated potassium bifluoride solution from readily available 2-chloroetha
Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides
Giel, Marie-Claire,Smedley, Christopher J.,Mackie, Emily R. R.,Guo, Taijie,Dong, Jiajia,Soares da Costa, Tatiana P.,Moses, John E.
supporting information, p. 1181 - 1186 (2019/12/11)
The boom in growth of 1,4-disubstituted triazole products, in particular, since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the CuI-catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click-inspired protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1-substituted-1,2,3-triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts.
Method for efficiently preparing sulfuryl fluorides compound by catalytic fluorination
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Paragraph 0093; 0094; 0095; 0096, (2019/05/22)
The invention belongs to the technical field of the chemical synthesis, and particularly relates to a method for efficiently preparing a sulfuryl fluorides compound by catalytic fluorination. The provided method for efficiently preparing the sulfuryl fluorides compound by the catalytic fluorination comprises the following steps: enabling a sulfonyl chlorides compound to react with a hydroge fluoride under the action of a catalyst of a sulfonic acids derivative, to obtain the sulfuryl fluorides compound. A novel catalytic technology is provided, and the method has extensive substrate applicability. Efficient catalytic efficiency and yield are expressed.
Sulfur(VI) fluoride compounds and methods for the preparation thereof
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Page/Page column 19; 36; 37; 51; 52, (2018/11/23)
This application describes a compound represented by Formula (I): (I) wherein: Y is a biologically active organic core group comprising one or more of an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group, to which Z is covalently bonded; n is 1, 2, 3, 4 or 5; m is 1 or 2; Z is O, NR, or N; X1 is a covalent bond or —CH2CH2—, X2 is O or NR; and R comprises H or a substituted or unsubstituted group selected from an aryl group, a heteroaryl aryl group, a nonaromatic hydrocarbyl group, and a nonaromatic heterocyclic group. Methods of preparing the compounds, methods of using the compounds, and pharmaceutical compositions comprising the compounds are described as well.
Evaluation and biological properties of reactive ligands for the mapping of the glycine site on the N-methyl-D-aspartate (NMDA) receptor
Kreimeyer, Annett,Laube, Bodo,Sturgess, Mike,Goeldner, Maurice,Foucaud, Bernard
, p. 4394 - 4404 (2007/10/03)
The glycine-binding site of the N-methyl-D-aspartate (NMDA) receptor, given its potential as pharmacological target, has been thoroughly studied by structure-activity relationships, which has made possible its description in terms of spatial limits and interactions of various types. A structural model, based on mutational analysis and sequence alignments, has been proposed. Yet, the amino acid residues responsible for the interactions with the ligand have not been unambiguously characterized. To evidence nucleophilic pocket-lining residues, we have designed and synthesized reactive glycine-site ligands derived from 3-substituted 4-hydroxy-quinolin- 2(1H)-ones by introducing various electrophilic groups at different positions of the molecule. These ligands were found to have high affinity at the glycine site and to be functional antagonists by inhibiting glycine/glutamate-induced currents in transfected oocytes. The correlation between their potency and their substitution pattern was strictly consistent with previously established structure-activity relationships. Most ligands displayed intrinsic reactivity toward cysteine, but none inactivated wild- type receptors. This is consistent with the model since it indicates the absence of exposed cysteine in the glycine-binding site. A strategy of cysteine incorporation by point mutations at selected polypeptide positions will create unambiguously localized targets for our reactive probes.
Hydrocarbylethyl sulfonyl fluoride
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, (2008/06/13)
Hydrocarbylethyl sulfonyl fluorides in which the hydrocarbyl substituent contains at least 3 carbon atoms, can be prepared by reacting 2-mercaptoethanol with chlorine to form chloroethyl sulfonyl chloride which is treated with aqueous potassium fluoride to yield chloroethyl sulfonyl fluoride, followed by treatment with magnesium oxide to yield vinyl sulfonyl fluoride. The vinyl sulfonyl fluoride is adducted to a hydrocarbyl substituent precursor, such as an olefin or halogenated olefin. A representative compound is polyisobutenyl sulfonyl fluoride. The hydrocarbylethyl sulfonamide products for which the hydrocarbylethyl sulfonyl fluorides are intermediates are useful as additives for lubricating oils.
