4640-29-3Relevant articles and documents
Iron-catalyzed arene C-H hydroxylation
Cheng, Lu,Wang, Huihui,Cai, Hengrui,Zhang, Jie,Gong, Xu,Han, Wei
, p. 77 - 81 (2021/10/05)
The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.
The design, synthesis, and evaluation of organ-specific iron chelators
Bergeron, Raymond J.,Wiegand, Jan,McManis, James S.,Bharti, Neelam
, p. 7032 - 7043 (2007/10/03)
A series of iron chelators, three (S)-4,5-dihydro-2-(2-hydroxyphenyl)-4- methyl-4-thiazolecarboxylic acid (DADFT) and three (S)-4,5-dihydro-2-(2- hydroxyphenyl)-4-thiazolecarboxylic acid (DADMDFT) analogues are synthesized and assessed for their lipophilicity (log Papp), iron-clearing efficiency (ICE) in rodents and iron-loaded primates (Cebus apella), toxicity in rodents, and organ distribution in rodents. The results lead to a number of generalizations useful in chelator design strategies. In rodents, while log Papp is a good predictor of a chelator's ICE, chelator liver concentration is a better tool. In primates, log Papp is a good predictor of ICE, but only when comparing structurally very similar chelators. There is a profound difference in toxicity between the DADMDFT and DADFT series: DADMDFTs are less toxic. Within the DADFT family of ligands, the more lipophilic ligands are generally more toxic. Lipophilicity can have a profound effect on ligand organ distribution, and ligands can thus be targeted to organs compromised in iron overload disease, for example, the heart.
Isolation of bright blue fluorescent substances from sonochemical hydroxylation of methyl p-cyanobenzoate
Yamada, Sachiko,Hokari, Hajime,Akasaka, Shinji,Iwamura, Michiko
, p. 197 - 198 (2007/10/03)
Sonochemical hydroxylation of methyl p-cyanobenzoate (1a) in water gave a bright blue fluorescence, which are mainly ascribed to three new fluorescent compounds, 3-hydroxy, 2,3- and 2,5-dihydroxy derivatives of 1a. Other benzenes substituted with electron-withdrawing groups also gave similar fluorescence from their hydroxylated derivatives. Among the fluorescence substances, methyl 2,5-dihydroxybenzoate was supposed to be applicable for a fluorescent chemosensor.