Application In Synthesis of 4′-Hydroxyacetophenone. Klinger, GE; Zhou, YT; Hao, PC; Robbins, J; Aquilina, JM; Jackson, JE; Hegg, EL in [Klinger, Grace E.; Hegg, Eric L.] Michigan State Univ, Dept Biochem & Mol Biol, 603 Wilson Rd, E Lansing, MI 48824 USA; [Klinger, Grace E.; Zhou, Yuting; Hao, Pengchao; Robbins, Jacob; Aquilina, Jake M.; Jackson, James E.] Michigan State Univ, Dept Chem, 578 S Shaw Ln, E Lansing, MI 48824 USA; [Klinger, Grace E.; Jackson, James E.; Hegg, Eric L.] Michigan State Univ, Great Lakes Bioenergy Res Ctr, 164 Food Safety & Toxicol Bldg, E Lansing, MI 48824 USA published Biomimetic Reductive Cleavage of Keto Aryl Ether Bonds by Small-Molecule Thiols in 2019.0, Cited 29.0. The Name is 4′-Hydroxyacetophenone. Through research, I have a further understanding and discovery of 99-93-4.
The nucleophilic and reductive properties of thiolates and thiols make them ideal candidates as redox mediators via the thiol/disulfide couple. One mechanism for biological lignin depolymerization entails reduction of keto aryl ether bonds by an S(N)2 mechanism with the thiol redox mediator glutathione. In this study, mimicking this chemistry in a simple protein- and metal-free process, several small organic thiols are surveyed for their ability to cleave aryl keto ethers that model the beta-O-4 linkages found in partially oxidized lignin. In polar aprotic solvents, beta-mercaptoethanol and dithiothreitol yielded up to 100 % formation of phenol and acetophenone products from 2-phenoxyacetophenone, but not from its reduced alcohol congener. The effects of reaction conditions and of substituents on the aryl rings and the keto ether linkage are assessed. These results, together with activation barriers computed by quantum chemical simulations and direct observation of the expected intermediate thioether, point to an S(N)2 mechanism. This study confirms that small organic thiols can reductively break down lignin-relevant keto aryl ether linkages.
Application In Synthesis of 4′-Hydroxyacetophenone. About 4′-Hydroxyacetophenone, If you have any questions, you can contact Klinger, GE; Zhou, YT; Hao, PC; Robbins, J; Aquilina, JM; Jackson, JE; Hegg, EL or concate me.
Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles