20397-61-9Relevant academic research and scientific papers
2-Diethoxyphosphoryl alcanoic acid dianions (lithium α-lithiocarboxylates) IV. A direct route to 2-fluoro-2-alkenoic acids by the Horner synthesis. Application in the field of pyrethroids
Coutrot, Ph.,Grison, C.,Sauvetre, R.
, p. 1 - 8 (1987)
2-Diethoxyphosphoryl-2-fluoroacetic acid was converted into the lithium α lithiocarboxylate dianion by treatment with n-butyllithium in hexane/tetrahydrofuran at -70 deg C.The Horner reaction between this new dianion and carbonyl compounds gave various 2-fluoro-2alkenoic acids.Application of the method to the cis,trans caronaldehyde ethyl esters led to the 2-fluoroethenyl pyrethroid derivatives (Z-cis, E-cis, Z-trans, E-trans).
Stereoconvergent Synthesis of Monofluoroalkenes via Photoinduced Dual Decarboxylative Cross-Coupling of α-Fluoroacrylic Acids with Redox-Active Esters
Lu, Xiao-Yu,Gao, Ang,Ge, Meng-Yuan,Xia, Ze-Jie,Liu, Qi-Le,Tao, Ting-Hua,Sun, Xiao-Mei
, p. 4654 - 4669 (2022/04/07)
Herein, a new strategy for the synthesis of monofluoroalkenes via employing α-fluoroacrylic acids and N-hydroxyphthalimide (NHPI) redox-active esters as coupling partners has been developed. This decarboxylative reaction enabled the formation of C(sp2)-C(sp3) bonds to provide a practical and efficient approach for the construction of a variety of monofluoroalkenes, which are key structural motifs in organic chemistry, under mild reaction conditions. The protocol exhibited excellent functional group compatibility and delivered monofluoroalkene products with excellent Z-stereoselectivity. This work also provides a platform for the modification of complex biologically active molecules containing carboxylic acids.
Fluorine-containing carboxylic acid compound and preparation method thereof
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Paragraph 0038-0048; 0054-0057, (2020/09/09)
The invention provides a fluorine-containing carboxylic acid compound and a preparation method and application thereof. The preparation method comprises the steps that a fluorine-containing olefin compound and CO2 react in a solvent in the presence of a c
Copper-Catalyzed Carboxylation of C-F Bonds with CO2
Yan, Si-Shun,Wu, Dong-Shan,Ye, Jian-Heng,Gong, Li,Zeng, Xin,Ran, Chuan-Kun,Gui, Yong-Yuan,Li, Jing,Yu, Da-Gang
, p. 6987 - 6992 (2019/08/26)
An effective Cu-catalyzed selective formal carboxylation of C-F bonds with an atmospheric pressure of CO2 is reported. A variety of gem-difluoroalkenes, gem-difluorodienes, and α-trifluoro-methyl alkenes show high reactivity and selectivity for
Development of the First Two-Pore Domain Potassium Channel TWIK-Related K+ Channel 1-Selective Agonist Possessing in Vivo Antinociceptive Activity
Vivier, Delphine,Soussia, Ismail Ben,Rodrigues, Nuno,Lolignier, Stéphane,Devilliers, Ma?ly,Chatelain, Franck C.,Prival, Laetitia,Chapuy, Eric,Bourdier, Geoffrey,Bennis, Khalil,Lesage, Florian,Eschalier, Alain,Busserolles, Jér?me,Ducki, Sylvie
, p. 1076 - 1088 (2017/02/19)
The TWIK-related K+ channel, TREK-1, has recently emerged as an attractive therapeutic target for the development of a novel class of analgesic drugs, suggesting that activation of TREK-1 could result in pain inhibition. Here, we report the synthesis of a series of substituted acrylic acids (1-54) based on our previous work with caffeate esters. The analogues were evaluated for their ability to modulate TREK-1 channel by electrophysiology and for their in vivo antinociceptive activity (acetic acid-induced writhing and hot plate assays), leading to the identification of a series of novel molecules able to activate TREK-1 and displaying potent antinociceptive activity in vivo. Furyl analogue 36 is the most promising of the series.
Stereospecific synthesis of tri- and tetrasubstituted α-fluoroacrylates by mizoroki-heck reaction
Rousée, Kevin,Bouillon, Jean-Philippe,Couve-Bonnaire, Samuel,Pannecoucke, Xavier
supporting information, p. 540 - 543 (2016/02/18)
Ligand-free, efficient, palladium-catalyzed Mizoroki-Heck reaction between methyl α-fluoroacrylate and arene or hetarene iodides is reported for the first time. The reaction is stereospecific and provides fair to quantitative yields of fluoroalkenes. The Mizoroki-Heck reaction starting from more hindered and usually reluctant trisubstituted acrylate, to access tetrasubstituted fluoroalkenes, is also reported. Finally, the use of a three-step synthesis sequence, including Mizoroki-Heck reaction, allows the synthesis of fluorinated analogues of therapeutic agents with high yield.
PAIN RELIEF COMPOUNDS
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Paragraph 0491, (2015/02/19)
The present invention relates to the use of compounds for the treatment or prevention of pain in mammals, in particularly in human beings, and also to a process for preparing these compounds.
A facile and mild approach for stereoselective synthesis of α-fluoro-α,β-unsaturated esters from α-fluoro-β-keto esters via deacylation
Qian, Jinlong,Yi, Wenbin,Lv, Meifang,Cai, Chun
, p. 127 - 132 (2015/02/02)
The highly stereoselective olefination reaction of α-fluoro-β-keto esters for the synthesis of α-fluoro-α,β-unsaturated esters has been developed. The olefination combines nucleophilic addition, intramolecular nucleophilic addition, and elimination in one step, as well as provides a facile synthetic approach to α-fluoro-α,β-unsaturated esters which are important units in many biologically active compounds and useful precursors in a variety of functional-group transformations.
An efficient synthesis of (Z)-α-fluorochalcones via the palladium-catalyzed cross-coupling reaction of (Z)-α-fluorocinnamoyl chloride with boronic acids
Eddarir, Said,Kajjout, Mohammed,Rolando, Christian
, p. 1735 - 1738 (2013/03/14)
An efficient synthesis of α-fluorochalcones (1,3-diphenyl-2- fluoroprop-2-en-1-one) based on the Suzuki-Miyaura palladium-catalyzed cross-coupling reaction of arylboronic acids with α-fluorocinnamoyl chlorides in the presence of Cs2CO3/su
Synthetic utilization of 2-chloro-1,1,1,2-tetrafluoroethane
Notsu, Keiji,Zushi, Yasuyuki,Ota, Shin,Kawasaki-Takasuka, Tomoko,Yamazaki, Takashi
experimental part, p. 9200 - 9208 (2011/09/19)
β-Substituted α-fluoro-α,β-unsaturated carboxylic acids have been successfully synthesized, usually in a (Z)-stereospecific manner by way of a stepwise or a one-pot three-step procedure starting from 2-chloro-1,1,1,2-tetrafluoroethane (HCFC-124), one of the major byproducts of the industrial process for tetrafluoroethene formation from chlorofluoromethane (HCFC-22). Get some Z's! β-Substituted α-fluoro-α,β- unsaturated carboxylic acids have been successfully synthesized from 2-chloro-1,1,1,2-tetrafluoroethane, one of the major byproducts of tetrafluoroethene formation from chlorofluoromethane. The products are usually obtained with Z stereoselectivity, by either a stepwise or a one-pot three-step procedure (see scheme).
