59907-65-2Relevant academic research and scientific papers
Design, synthesis, and structure-activity relationships of a series of novel N-aryl-2-phenylcyclopropanecarboxamide that are potent and orally active orexin receptor antagonists
Yoshida, Yu,Terauchi, Taro,Naoe, Yoshimitsu,Kazuta, Yuji,Ozaki, Fumihiro,Beuckmann, Carsten T.,Nakagawa, Makoto,Suzuki, Michiyuki,Kushida, Ikuo,Takenaka, Osamu,Ueno, Takashi,Yonaga, Masahiro
, p. 6071 - 6088 (2015/02/02)
Herein we describe the design, synthesis, and structure-activity relationships (SARs) of a novel phenylcyclopropane series represented by 7 and 33b as antagonists of orexin 1 and orexin 2 receptors. With 4 serving as the initial lead for the development o
Preparation of Regioselectively Protected Hydroquinones by Phosphorylation of p-Benzoquinones with Trialkyl Phosphites
Duthaler, Rudolf O.,Lyle, Paulette A.,Heuberger, Christoph
, p. 1406 - 1426 (2007/10/02)
The title reaction has been applied to 10 monosubstituted p-benzoquinones (Scheme 2, Table).The regioselectivity of the O-phosphorylation is influenced by bulky substituents (t-butyl and trimethylsilyl) and, electronically, by the methoxy group.The regioselectivity, which is high in nonpolar media (benzene), is lower in polar solvents (CH2Cl2 and CH3CN).The synthetic potential of this transformation, exemplified by the preparation of compounds 29 (Scheme 3) and 32 (Scheme 4), is considerably extended by applying milder methods for the phosphate hydrolysis and by using the reagent couple P(OCH3)3/trimethylsilyl chloride, which gives clean access to p-hydroxyphenyl phosphates. p-Benzoquinones 4h and 4i with strong ?-acceptor substituents react in a different way, giving phosphonates.The electronically induced regioselectivity of the O- and C-phosphorylation is in accordance with the preferences expected for the attack by a nucleophilic phosphorylation agent.
