2940-56-9Relevant academic research and scientific papers
Copper-Catalyzed Enantioconvergent Cross-Coupling of Racemic Alkyl Bromides with Azole C(sp2)?H Bonds
Chang, Xiao-Yong,Chen, Ji-Jun,Gu, Qiang-Shuai,Jiang, Sheng-Peng,Li, Zhong-Liang,Liu, Lin,Liu, Xiao-Dong,Liu, Xin-Yuan,Su, Xiao-Long,Wang, Fu-Li,Yang, Chang-Jiang,Ye, Liu
, p. 380 - 384 (2020/10/30)
The development of enantioconvergent cross-coupling of racemic alkyl halides directly with heteroarene C(sp2)?H bonds has been impeded by the use of a base at elevated temperature that leads to racemization. We herein report a copper(I)/cinchona-alkaloid-derived N,N,P-ligand catalytic system that enables oxidative addition with racemic alkyl bromides under mild conditions. Thus, coupling with azole C(sp2)?H bonds has been achieved in high enantioselectivity, affording a number of potentially useful α-chiral alkylated azoles, such as 1,3,4-oxadiazoles, oxazoles, and benzo[d]oxazoles as well as 1,3,4-triazoles, for drug discovery. Mechanistic experiments indicated facile deprotonation of an azole C(sp2)?H bond and the involvement of alkyl radical species under the reaction conditions.
Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes
Chen, Shuming,Gieuw, Matthew H.,Houk, K. N.,Ke, Zhihai,Yeung, Ying-Yeung
, p. 9426 - 9433 (2020/10/02)
Although radical formation from a trialkylborane is well documented, the analogous reaction mode is unknown for trihaloboranes. We have discovered the generation of bromine radicals from boron tribromide and simple proton sources, such as water ortert-butanol, under open-flask conditions. Cyclopropanes bearing a variety of substituents were hydro- and deuterio-brominated to furnish anti-Markovnikov products in a highly regioselective fashion. NMR mechanistic studies and DFT calculations point to a radical pathway instead of the conventional ionic mechanism expected for BBr3
Glucose transport-enhancing and hypoglycemic activity of 2-methyl-2- phenoxy-3-phenylpropanoic acids
Sarges,Hank,Blake,Bordner,Bussolotti,Hargrove,Treadway,Gibbs
, p. 4783 - 4803 (2007/10/03)
A series of 2-phenoxy-3-phenylpropanoic acids has been prepared which contains many potent hypoglycemic agents as demonstrated by assessing glucose lowering in ob/ob mice. Some compounds (32, 33, 59) normalize plasma glucose in this diabetic model at doses of approximately 1 mg/kg. The mechanism of action of these drugs may involve enhanced glucose transport, especially in fat cells, but the compounds do not stimulate GLUT4 translocation and do not increase the levels of GLUT1 or GLUT4 in vivo. Thus, these compounds may enhance the intrinsic activity of the glucose transporter GLUT1 or GLUT4. Some compounds also modestly decrease hepatocyte gluconeogenesis in vitro, but this is not likely to be a major contributor to the hypoglycemic effect observed in vivo. Likewise, a modest decrease in food consumption observed with some of these compounds was shown by a pair-feeding experiment not to be the primary cause of the hypoglycemia observed.
Synthesis of 3-Phenoxybenzyl 3-Alkyl-3-phenyl-/p-substituted phenyl and 3-Phenoxybenzyl 2-Alkyl-3-phenyl-/p-substituted phenylpropionates
Kelkar, S. V.,Joshi, G. S.,Kulkarni, G. H.,Mitra, R. B.
, p. 68 - 70 (2007/10/02)
Some 3-phenoxybenzyl 3-alkyl-3-phenyl-/p-substituted phenylpropionates (VII, XI, XV, XIX, XXIII, XXVII) which resemble structurally the 1,2-secopyrethroids, have been prepared employing simple reactions like alkylation, decarbethoxylation and transesterification.The synthesis of 3-phenoxybenzyl 2-alkyl-3-phenyl-/p-substituted phenyl-propionates (XXXI, XXXII, XXXIII, and XXXVI) bearing close structural resemblance to 2,3-secopyrethroids has also been described.
