252893-52-0Relevant academic research and scientific papers
Copper-catalyzed method for preparing aldehyde or ketone compound by oxidizing alcohol with oxygen as oxidizing agent and application
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Paragraph 0028-0030; 0034-0036, (2020/08/18)
The invention discloses a copper-catalyzed method for preparing an aldehyde or ketone compound by oxidizing alcohol with oxygen as an oxidizing agent. Reaction is performed in an organic solvent for 4-48 hours at room temperature by using copper salt and nitroxide free radicals as catalysts and oxygen or air as an oxidizing agent to efficiently oxidize an alcohol compound into the corresponding aldehyde or ketone compound. The method is simple to operate, free of chlorides corrosive to equipment, available in raw materials and reagents, mild in reaction conditions, wide in substrate universality, good in functional group compatibility, convenient in separation and purification, environmentally friendly in the whole process and free of pollution, and is a method suitable for industrial production.
Laccase-mediated Oxidations of Propargylic Alcohols. Application in the Deracemization of 1-arylprop-2-yn-1-ols in Combination with Alcohol Dehydrogenases
González-Granda, Sergio,Méndez-Sánchez, Daniel,Lavandera, Iván,Gotor-Fernández, Vicente
, p. 520 - 527 (2019/11/16)
The catalytic system composed by the laccase from Trametes versicolor and the oxy-radical TEMPO has been successfully applied in the sustainable oxidation of fourteen propargylic alcohols. The corresponding propargylic ketones were obtained in most cases in quantitative conversions (87–>99 % yield), demonstrating the efficiency of the chemoenzymatic methodology in comparison with traditional chemical oxidants, which usually lead to problems associated with the formation of by-products. Also, the stereoselective reduction of propargylic ketones was studied using alcohol dehydrogenases such as the one from Ralstonia species overexpressed in E. coli or the commercially available evo-1.1.200, allowing the access to both alcohol enantiomers mostly with complete conversions and variable selectivities depending on the aromatic pattern substitution (97–>99 % ee). To demonstrate the compatibility of the laccase-mediated oxidation and the alcohol dehydrogenase-catalyzed bioreduction, a deracemization strategy starting from the racemic compounds was developed through a sequential one-pot two-step process, obtaining a selection of (S)- or (R)-1-arylprop-2-yn-1-ols with excellent yields (>98 %) and selectivities (>98 % ee) depending on the alcohol dehydrogenase employed.
Direct spirocyclization from keto-sulfonamides: An approach to azaspiro compounds
Beltran, Frédéric,Fabre, Indira,Ciofini, Ilaria,Miesch, Laurence
supporting information, p. 5042 - 5045 (2017/11/06)
Spontaneous spirocyclization of keto-sulfonamides via ynamides through a one-pot process is presented. Push-pull ynamides were obtained through Michael addition/elimination without Cu. The obtained azaspiro compounds are building blocks for indole alkaloids. Theoretical studies provide insights into the mechanism of the formal Conia-ene reaction.
Parallel synthesis of "Click" chalcones as antitubulin agents
Utsintong, Maleeruk,Massarotti, Alberto,Caldarelli, Antonio,Theeramunkong, Sewan
, p. 510 - 516 (2013/07/28)
It has been shown that some chalcones are able to inhibit tubulin polymerization, giving cytotoxicity and destruction of tumoral vasculature. A library of 180 novel chalcone analogs has been synthesized via click chemistry and screened for their cytotoxic
Structural characterization of crystalline inclusion complexes formed from 1,3,5-triaroylbenzene derivatives - A new family of inclusion hosts
Pigge, F. Christopher,Ghasedi, Fatemeh,Zheng, Zhanmiao,Rath, Nigam P.,Nichols, Gary,Chickos, James S.
, p. 2458 - 2464 (2007/10/03)
A series of crystalline inclusion complexes formed from substituted 1,3,5-triaroylbenzene hosts and small molecule guests has been structurally characterized by X-ray crystallography. The new inclusion hosts examined do not possess functional groups capab
A new inclusion host: An inclusion complex between a 1,3,5-triaroylbenzene host and a benzene guest stabilized by aromatic C-H···O hydrogen bonds
Pigge, F. Christopher,Ghasedi, Fatemeh,Rath, Nigam P.
, p. 8045 - 8048 (2007/10/03)
A methoxy-functionalized C3-symmetrical 1,3,5-triaroylbenzene derivative was prepared by cyclotrimerization of a substituted aryl ethynyl ketone. This material was found to form a stable inclusion complex with benzene in a host:guest ratio of 1:1 as revealed by X-ray crystallography. The solid state structure appears to be stabilized by aromatic C-H···O hydrogen bonds between the benzene guest and the triaroylbenzene host.
