20808-12-2Relevant articles and documents
Novel process for synthesizing 2 -fluorocyclopropylamine with high selectivity and asymmetric synthesis
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Paragraph 0049-0051, (2021/10/13)
A novel highly selective asymmetric synthesis process of 2 -fluorocyclopropylamine (Structural I). The method provided by the invention uses 1 - fluorine -1 - benzene (propylene) sulfonyl methane and chiral epichlorohydrin to construct chiral cyclopropane under basic conditions, and a new synthetic route not only achieves a special cis-trans selectivity, but also has a highly specific stereoselectivity. The synthesis route is efficient, the reaction condition is mild, the method is suitable for large industrial production in a green environment, 2 -fluorocyclopropylamine production cost is greatly reduced.
Highly stereoselective monofluoroolefination: Facile access to (E)-α-fluorinated arylvinyl sulfones from trifluoromethyl α-fluorinated arylsulfonyl gem-diols
Fang, Xiang,Zhou, Jun,Wang, Wang,Yang, Xueyan,Wu, Fanhong
, (2020/04/28)
An excellent stereoselective direct synthesis of trisubstituted (E)-α-fluorinated arylvinyl sulfones employing trifluoromethyl α-fluorinated arylsulfonyl gem-diols and aryl aldehydes under mild reaction conditions has been developed, which affords α-fluorinated arylvinyl sulfones in high yields with E-isomer only. The desired products can be further transformed into more useful fluoroolefins through debenzenesulfonyl process.
Controlled α-mono- and α,α-di-halogenation of alkyl sulfones using reagent-solvent halogen bonding
Poteat, Christopher M.,Lindsay, Vincent N. G.
supporting information, p. 2912 - 2915 (2019/03/17)
The direct and selective α-mono-bromination of alkyl sulfones was achieved through base-mediated electrophilic halogenation. The appropriate combination of solvent and electrophilic bromine source was found to be critical to control the nature of the products formed, where reagent-solvent halogen bonding is proposed to control the selectivity via alteration of the effective size of the electrophilic bromine source. Conversely, the α,α-di-brominated sulfones were selectively obtained in good yields following polyhalogenation followed by selective de-halogenation during workup. Both procedures can be applied on gram scale, and the mono-halogenation was successfully extended to the fully selective α-chlorination, α-iodination and α-fluorination of alkyl sulfones.
AZETIDINE DERIVATIVE, PREPARATION METHOD THEREFOR, AND USE THEREOF
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Paragraph 0225; 0227, (2018/08/29)
The present invention relates to an azetidine derivative for use as a Janus kinase (JAK) inhibitor, a drug composition comprising same, a preparation method therefor, and a use thereof in the treatment of JAK-related diseases comprising, for example, infl
Copper-Mediated Di- and Monofluoromethanesulfonylation of Arenediazonium Tetrafluoroborates: Probing the Fluorine Effect
Xing, Bo,Ni, Chuanfa,Hu, Jinbo
, p. 206 - 212 (2018/02/06)
A copper-mediated di- and monofluoromethanesulfonylation of arenediazonium tetrafluoroborates using di- and monofluoromethanesulfinate reagents provides aryl difluoromethyl (or monofluoromethyl) sulfones in good yields. It was found that the relative reactivity of these sodium fluoroalkanesulfinates in the present reactions decreases in the following order: CH2FSO2Na > CF2HSO2Na > CF3SO2Na.
BICYCLIC AZA COMPOUNDS AS MUSCARINIC M1 RECEPTOR AGONISTS
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, (2014/04/04)
This invention relates to compounds (Formula (1)) that are agonists of the muscarinic M1 receptor and which are useful in the treatment of muscarinic M1 receptor mediated diseases. Also provided are pharmaceutical compositions containing the compounds and
Enabling nucleophilic substitution reactions of activated alkyl fluorides through hydrogen bonding
Champagne, Pier Alexandre,Pomarole, Julien,Therien, Marie-Eve,Benhassine, Yasmine,Beaulieu, Samuel,Legault, Claude Y.,Paquin, Jean-Francois
supporting information, p. 2210 - 2213 (2013/06/26)
It was discovered that the presence of water as a cosolvent enables the reaction of activated alkyl fluorides for bimolecular nucleophilic substitution reactions. DFT calculations show that activation proceeds through stabilization of the transition structure by a stronger F···H 2O interaction and diminishing C-F bond elongation, and not simple transition state electrostatic stabilization. Overall, the findings put forward a distinct strategy for C-F bond activation through H-bonding.
Nucleophilic fluoroalkylation of α,β-unsaturated carbonyl compounds with α-fluorinated sulfones: Investigation of the reversibility of 1,2-additions and the formation of 1,4-adducts
Shen, Xiao,Ni, Chuanfa,Hu, Jinbo
, p. 2043 - 2051 (2013/01/15)
A detailed investigation of the reactions of PhSO2CF 2H and PhSO2CH2F with (E)-chalcone (=(E)-1,3-diphenylprop-2-en-1-one) at low temperatures revealed that these two reactions were kinetically controlled, and the ratios of 1,2- vs. 1,4-adducts, which did not change much over time at these temperatures, reflect the relative rates of the two reaction pathways. The controlled experiments of converting the PhSO2CF2- and PhSO2CHF-substituted 1,2-adducts to 1,4-adducts showed that these isomerizations are not favored due to the low stability and hard-soft nature of PhSO2CF2- and PhSO2CHF- anions. Moreover, taking advantage of the remarkable stability and softness of (PhSO2)2CF - anion, an efficient thermodynamically controlled isomerization of (PhSO2)2CF-substituted 1,2-adduct to 1,4-adduct was achieved for the first time. Copyright
Chemistry of trichlorofluromethane: Synthesis of chlorofluromethyl phenyl sulfone and fluoromethyl phenyl sulfone and some of their reactions
Saikia,Tsuboi
, p. 643 - 647 (2007/10/03)
It was observed that the reaction of CFCl3 with thiophenoxide gave only 10% of the corresponding thioether. On the other hand, these thioethers could be prepared in excellent yield from diaryl disulfides and CFCl3 in the presence of sodium hydroxymethanesulfinate in aqueous DMF at 4 atm pressure of nitrogen. Dechlorination of the thioether (PhSCFCl2) with different reducing agents were studied. Most of the reducing agents eliminated both fluorine and chlorine functionalities or gave the hydrolyzed products. But its sulfone on treatment with Zinc in methanol gave monochlorofluoromethyl and fluoromethyl phenyl sulfone in good yields. Darzens reaction of these compounds was also studied.