99062-31-4Relevant academic research and scientific papers
Distal γ-C(sp3)?H Olefination of Ketone Derivatives and Free Carboxylic Acids
Fan, Zhoulong,Park, Han Seul,Yu, Jin-Quan,Zhu, Ru-Yi
supporting information, p. 12853 - 12859 (2020/06/10)
Reported herein is the distal γ-C(sp3)?H olefination of ketone derivatives and free carboxylic acids. Fine tuning of a previously reported imino-acid directing group and using the ligand combination of a mono-N-protected amino acid (MPAA) and an electron-deficient 2-pyridone were critical for the γ-C(sp3)?H olefination of ketone substrates. In addition, MPAAs enabled the γ-C(sp3)?H olefination of free carboxylic acids to form diverse six-membered lactones. Besides alkyl carboxylic acids, benzylic C(sp3)?H bonds also could be functionalized to form 3,4-dihydroisocoumarin structures in a single step from 2-methyl benzoic acid derivatives. The utility of these protocols was demonstrated in large scale reactions and diversification of the γ-C(sp3)?H olefinated products.
Carbon chain shape selectivity by the mouse olfactory receptor OR-I7
Liu, Min Ting,Ho, Jianghai,Liu, Jason Karl,Purakait, Radhanath,Morzan, Uriel N.,Ahmed, Lucky,Batista, Victor S.,Matsunami, Hiroaki,Ryan, Kevin
, p. 2541 - 2548 (2018/04/12)
The rodent OR-I7 is an olfactory receptor exemplar activated by aliphatic aldehydes such as octanal. Normal alkanals shorter than heptanal bind OR-I7 without activating it and hence function as antagonists in vitro. We report a series of aldehydes designed to probe the structural requirements for aliphatic ligand chains too short to meet the minimum approximate 6.9 ? length requirement for receptor activation. Experiments using recombinant mouse OR-I7 expressed in heterologous cells show that in the context of short aldehyde antagonists, OR-I7 prefers binding aliphatic chains without branches, though a single methyl on carbon-3 is permitted. The receptor can accommodate a surprisingly large number of carbons (e.g. ten in adamantyl) as long as the carbons are part of a conformationally constrained ring system. A rhodopsin-based homology model of mouse OR-I7 docked with the new antagonists suggests that small alkyl branches on the alkyl chain sterically interfere with the hydrophobic residues lining the binding site, but branch carbons can be accommodated when tied back into a compact ring system like the adamantyl and bicyclo[2.2.2]octyl systems.
Iridium-catalyzed ring cleavage reaction of cyclobutanone O-benzoyloximes providing nitriles
Nishimura, Takahiro,Yoshinaka, Tomoaki,Nishiguchi, Yoshiki,Maeda, Yasunari,Uemura, Sakae
, p. 2425 - 2427 (2007/10/03)
(Chemical Equation Presented) Iridium-catalyzed ring cleavage reaction of cyclobutanone O-benzoyloximes in the presence of 9,10-dihydroanthracene and potassium carbonate proceeds to give saturated nitriles via C-C bond fission at the sterically more hinde
