5079-90-3Relevant articles and documents
Ru-catalyzed (E)-specific ortho-C-H alkenylation of arenecarboxylic acids by coupling with alkenyl bromides
Belitz, Florian,Goo?en, Lukas J.,Hu, Zhiyong,Papp, Florian,Zhang, Guodong
supporting information, p. 3541 - 3545 (2021/05/31)
In the presence of [p-cymene)RuCl2]2, (E)-configured alkenyl bromides couple with aromatic carboxylates to form ortho-vinylbenzoic acids. This C-H vinylation proceeds in high yields without any activating phosphine ligands and has an excellent functional group tolerance. Starting from commonly available (E/Z)-mixtures of alkenyl bromides, (E)-configured vinyl arenes or dienes are formed exclusively. Mechanistic studies show that this selectivity is achieved because the (E)-configured alkenyl bromides undergo a smooth coupling, whereas the (Z)-isomers are rapidly eliminated with the formation of alkynes.
Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity
Fujii, Yoshiharu,Iwata, Takayuki,Kano, Arihiro,Kodama, Kozue,Makigawa, Saki,Matsumoto, Kenji,Morita, Miyo Terao,Shindo, Mitsuru,Sugiyama, Hiromi,Wasano, Naoya
, (2020/09/09)
Previously, we found (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) to be a selective inhibitor of root gravitropic bending of lettuce radicles at 5 μM, with no concomitant growth inhibition, and revealed the structure–activity relationship in this inhibitory activity. The conformation of ku-76 is flexible owing to the open-chain structure of pentan-2,4-dienoic acid with freely rotating single bonds, and the (2Z)-alkene moiety may be isomerized by external factors. To develop more potent inhibitors and obtain insight into the target biomolecules, various analogues of ku-76, fixed through conformation and/or configuration, were synthesized and evaluated. Stereochemical fixation was effective in improving the potency of gravitropic bending inhibition. Finally, we found highly potent conformational and/or configurational analogues (ku-257, ku-294 and ku-308), that did not inhibit root growth. The inhibition of root curvature by these analogues was comparable to that of naptalam.
trans-Cyclooctenes as Halolactonization Catalysts
Einaru, Shunsuke,Shitamichi, Kenta,Nagano, Tagui,Matsumoto, Akira,Asano, Keisuke,Matsubara, Seijiro
, p. 13863 - 13867 (2018/09/27)
The strained olefins in trans-cyclooctenes serve as efficient catalysts for halolactonizations, including bromolactonizations and iodolactonizations. The trans-cyclooctene framework is essential for excellent catalytic performance, and the substituents also play important roles in determining efficiency. These results are the first demonstration of catalysis by a trans-cyclooctene.
