405-50-5Relevant articles and documents
Potential proinsecticides of fluorinated carboxylic acids and β-ethanolamines. IV. Evaluation of the Δ2-oxazoline-1,3 structure by 19F NMR monitoring of the in vitro metabolism in locust tissues
Cherton,Hamm,Halle,Menguy,Beaufour
, p. 387 - 395 (2001)
The enzymatic effect of locust tissues upon hydrolysis of the fluorinated Δ2-oxazoline-1,3 Ia was elucidated using 19F[1H] NMR monitoring. In a phosphate buffer at pH = 7.4 (mean physiological pH of locust tissues), the substrate Ia hydrolyses slowly into the corresponding fluorinated hydroxylamide VIa. If diluted, locust haemolymph (12.5% in phosphate buffer) catalyses slightly this hydrolytic pathway, it overall triggers the unmasking of carboxylate IIIa, corresponding to the expected proinsecticide behaviour of Ia. This behaviour is spectacularly almost the unique reaction observed during in vitro assays in concentrated fat body and mesenteron. Inasmuch as β-hydroxylamide VIa is not hydrolysed into carboxylate IIIa during such conditions, it must be concluded that carboxylate formation exclusively results from hydration and hydrolysis of substrate Ia via the aminoester Va. The formation of this intermediate aminoester is demonstrated by complementary assays. The enzymes supposed to intervene are of the α-chymotrypsine type for the first step (hydration) and of the esterase type for subsequent hydrolysis of intermediate aminoester Va. Thus, this work constitutes the first example of a Δ2-oxazoline-1,3 structure exploited for elaborating proinsecticides of carboxylates III and/or β-ethanolamines II based on enzymatic activation in insects.
Desulfonylative Electrocarboxylation with Carbon Dioxide
Zhong, Jun-Song,Yang, Zi-Xin,Ding, Cheng-Lin,Huang, Ya-Feng,Zhao, Yi,Yan, Hong,Ye, Ke-Yin
supporting information, p. 16162 - 16170 (2021/09/02)
Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO2) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. Such a strategy takes advantage of CO2as the abundant C1 building block for the facile preparation of multifunctionalized carboxylic acids, including the nonsteroidal anti-inflammatory drug ibuprofen, under mild reaction conditions.
Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides
Li, Chenchen,Li, Ruoling,Zhang, Bing,Zhao, Pei,Zhao, Wanxiang
supporting information, p. 10913 - 10917 (2020/05/25)
A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.