64315-36-2Relevant articles and documents
Ortho-Selective Hydrogen Isotope Exchange of Phenols and Benzyl Alcohols by Mesoionic Carbene-Iridium Catalyst
Zhao, Liang-Liang,Wu, Yixin,Huang, Shiqing,Zhang, Zengyu,Liu, Wei,Yan, Xiaoyu
supporting information, p. 9297 - 9302 (2021/11/30)
Hydrogen isotope exchange reactions of phenols and benzyl alcohols have been achieved by a mesoionic carbene-iridium catalyst with high ortho selectivity and high functional group tolerance. Control experiments indicated that acetate is crucial to realize the ortho selectivity, whereas density functional theory calculations supported an outer-sphere direction with hydrogen bonding between acetate and the hydroxyl group.
H-D Exchange Deuteration of Arenes at Room Temperature
Sawama, Yoshinari,Nakano, Akihiro,Matsuda, Takumi,Kawajiri, Takahiro,Yamada, Tsuyoshi,Sajiki, Hironao
supporting information, p. 648 - 653 (2019/02/14)
Arene nuclei efficiently underwent the hydrogen (H)-deuterium (D) exchange reaction catalyzed by platinum group metals on carbon in a mixed solvent of 2-propanol and D2O at room temperature to produce deuterium-labeled arenes. Platinum on carbon (Pt/C) and iridium on carbon (Ir/C) were applicable catalysts, and the various arenes bearing a carbonyl group, fluorine, phenolic hydroxy group, amino group, or phosphonic acid on the aromatic nucleus were effectively deuterated. Nonheating conditions are valuable for the scalable industrial preparation.
Synthesis of labeled ambroxol and its major metabolites
Latli, Bachir,Hrapchak, Matt,Switek, Heinz-Karl,Retz, Daniel M.,Krishnamurthy, Dhileepkumar,Senanayake, Chris H.
experimental part, p. 15 - 23 (2010/04/26)
Ambroxol is a mucolytic agent used in the treatment of respiratory diseases. Herein, we report the synthesis of carbon-14-labeled ambroxol with the radioactive atom(s) either on the benzylic carbon or uniformly in the cyclohexyl ring with specific activities of 59 and 81 mCi/mmol, respectively. We also describe the preparation of deuterium-labeled ambroxol, its deuterium-labeled tetrahydroquinazoline metabolite (DHTQ), carbon-13-labeled 3,5-dibromoanthranilic acid metabolite, as well as an unlabeled O-glucuronide conjugate. Copyright
A simple procedure for the deuteriation of phenols
Tuck, Kellie L.,Tan, Hai-Wei,Hayball, Peter J.
, p. 817 - 823 (2007/10/03)
A simple procedure for the deuteriation of a large range of phenols has been developed using Amberlyst 15, a polymer supported acid catalyst. A number of phenols present in olive oil have been successfully deuteriated. The aromatic protons of hydroxytyrosol are 100% exchanged under the conditions used. This method is applicable for the tritiation of phenols.
