95416-60-7Relevant articles and documents
Access to Trisubstituted Fluoroalkenes by Ruthenium-Catalyzed Cross-Metathesis
Nouaille, Augustin,Pannecoucke, Xavier,Poisson, Thomas,Couve-Bonnaire, Samuel
supporting information, p. 2140 - 2147 (2021/03/06)
Although the olefin metathesis reaction is a well-known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross-Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post-functionalizable source of fluoroalkene, that we found as the methyl 2-fluoroacrylate. We reported herein the efficient ruthenium-catalyzed CM reaction of various terminal and internal alkenes with methyl 2-fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products. (Figure presented.).
Synthesis of tetra-pincer nickel(ii) and palladium(ii) complexes of resorcin[4]arene-octophosphinite [Res(OPR2)8] and rhodium-catalyzed regioselective hydroformylation reaction
Ananthnag, Guddekoppa S.,Mondal, Dipanjan,Mague, Joel T.,Balakrishna, Maravanji S.
, p. 14632 - 14641 (2019/10/16)
The condensation reaction of resorcinol with pentanal yielded resorcin[4]arene 1 which on bromination using N-bromosuccinimide at room temperature produced tetra-bromide derivative 2. The reactions of 2 with chlorodiphenylphosphine and o-phenylenephosphoro-chloridite yielded octaphosphinite 3 (hereafter referred to as octaphos) and octaphosphite 4, respectively. The reactions of 3 with Ni(COD)2 or Pd2(dba)3·CHCl3 in appropriate molar ratios yielded tetra-pincer complexes 5 and 6, respectively. The structures of both the complexes were established by single crystal X-ray diffraction studies. The resorcin[4]arene backbone adopts a boat structure in these complexes. Typically, the Rh-catalyzed hydroformylation of styrene prevalently delivers a branched (b) chiral aldehyde. A unique resorcin[4]arene skeleton based octaphos 3 was employed in the Rh-catalyzed hydroformylation of styrene. The hydroformylation of styrene with a metal to ligand ratio of 1:1 (M:L) was found to be regioselective, producing a linear (l) aldehyde as a major product with 100% conversion in 3 h. The l:b ratio surprisingly increased when the ortho positions of styrene were populated by methyl and chloro substituents. The hydroformylation of p-nitro styrene triggered a remarkably high linear:branched aldehyde ratio of 2.4 (71% linear aldehyde) despite its electron withdrawing nature. The highest linear selectivity of 97% (l:b ratio 27.8) was achieved in the case of 2,4,6-trimethylstyrene.
Synthesis and in vitro antiproliferative activity of C5-benzyl substituted 2-amino-pyrrolo[2,3-d]pyrimidines as potent Hsp90 inhibitors
Lee, Ju-Hyeon,Shin, Sang Chul,Seo, Seon Hee,Seo, Young Ho,Jeong, Nakcheol,Kim, Chan-Wha,Kim, Eunice EunKyeong,Keum, Gyochang
supporting information, p. 237 - 241 (2016/12/27)
A novel series of heat shock protein 90 (Hsp90) inhibitors was identified by X-ray crystal analysis of complex structures at solvent-exposed exit pocket C. The 2-amino-pyrrolo[2,3-d]pyrimidine derivatives, 7-deazapurines substituted with a benzyl moiety at C5, showed potent Hsp90 inhibition and broad-spectrum antiproliferative activity against NCI-60 cancer cell lines. The most potent compound, 6a, inhibited Hsp90 with an IC50of 36?nM and showed a submicromolar mean GI50value against NCI-60 cell lines. The interaction of 6a at the ATP-binding pocket of Hsp90 was confirmed by X-ray crystallography and Western blot analysis.
