4420-58-0Relevant academic research and scientific papers
Phenanthrene Synthesis by Palladium(II)-Catalyzed γ-C(sp2)-H Arylation, Cyclization, and Migration Tandem Reaction
Gou, Bo-Bo,Yang, Hui,Sun, Huai-Ri,Chen, Jie,Wu, Junliang,Zhou, Ling
supporting information, p. 80 - 84 (2019/01/11)
Phenanthrene is an important structural motif in chemistry and materials science, and many synthetic routes have been developed to construct its skeleton. However, synthesis of unsymmetric phenanthrenes remains a challenge. Here, an efficient one-pot tandem reaction for the preparation of phenanthrenes via sequential γ-C(sp2)-H arylation, cationic cyclization, dehydration, and 1,2-migration was developed. A wide range of symmetric and unsymmetric phenanthrenes with diversified functional groups were synthesized with good to excellent yields.
Transfer Hydrocyanation of α- and α,β-Substituted Styrenes Catalyzed by Boron Lewis Acids
Orecchia, Patrizio,Yuan, Weiming,Oestreich, Martin
supporting information, p. 3579 - 3583 (2019/02/05)
A straightforward gram-scale preparation of cyclohexa-1,4-diene-based hydrogen cyanide (HCN) surrogates is reported. These are bench-stable but formally release HCN and rearomatize when treated with Lewis acids. For BCl3, the formation of the isocyanide adduct [(CN)BCl3]? and the corresponding Wheland complex was verified by mass spectrometry. In the presence of 1,1-di- and trisubstituted alkenes, transfer of HCN from the surrogate to the C?C double bond occurs, affording highly substituted nitriles with Markovnikov selectivity. The success of this transfer hydrocyanation depends on the Lewis acid employed; catalytic amounts of BCl3 and (C6F5)2BCl are shown to be effective while B(C6F5)3 and BF3?OEt2 are not.
Synthesis, antimuscarinic activity and quantitative structure-activity relationship (QSAR) of tropinyl and piperidinyl esters
Xu, Rong,Sim, Meng-Kwoon,Go, Mei-Lin
, p. 231 - 241 (2007/10/03)
A series of tropinyl and piperidinyl esters was synthesized and evaluated for inhibitory activities on the endothelial muscarinic receptors of rat (M3) and rabbit (M2) aorta. Some of the esters (cyclohexylphenylglycolates and cyclohexylphenylpropionates) were found to be better antimuscarinic compounds than standard M2 and M3 inhibitors such as AFDX116 and 4-diphenylacetoxy-N-methylpiperidine (DAMP), with pKEC50 values in the range of 8-9. A few esters were found to be more selective M3 than M2 inhibitors, but these tended to have low activities. The hydrophobic, electronic and steric characteristics of these esters were correlated with antimuscarinic activity by using appropriate parameters representing hydrophobicity (HPLC capacity factor, log k(w), size (molecular volume) and electronic character (Taft's polar substituent constant δ and 13C chemical shift difference Δδ). Finally, 92% of the M2-inhibitory activities of the esters could be accounted for by the size and electronic character σ* of the side chain. In contrast, the M3-inhibitory activities of these esters were mainly attributed to the electronic nature (σ*, Δδ) of the side chain, with good activity being associated with electron-withdrawing groups. Visualization of the comparative molecular field analysis (CoMFA) steric and electrostatic fields provided further confirmation of the structure-activity relationship (SAR) derived from traditional quantitative structure-activity relationship (QSAR) approaches.
Muscarinic Receptor Subtype Specificity of (N,N-Dialkylamino)alkyl 2-Cyclohexyl-2-phenylpropionates: Cylexphenes (Cyclohexyl-Substituted Aprophen Analogues)
Leader, Haim,Gordon, Richard K.,Baumgold, Jesse,Boyd, Victoria L.,Newman, Amy H.,et al.
, p. 1290 - 1295 (2007/10/02)
A series of aprophen analogues, called cylexphenes, were synthesized with alterations in (1) the chain length of the amine portion of the ester, (2) the alkyl groups on the amino alcohol and (3) a cyclohexy
