1611-07-0Relevant articles and documents
Synthesis and antioxidant activities of 3,5-dialkoxy-4-hydroxycinnamamides
Kang, Tae-Souk,Jo, Hyang-Ok,Park, Woo-Kyu,Kim, Jong-Pyung,Konishi, Yasuo,Kong, Jae-Yang,Park, No-Sang,Jung, Young-Sik
, p. 1663 - 1667 (2008/12/21)
A series of 3,5-dialkoxy-4-hydroxycinnamamides 6 and 7 was synthesized, and their antioxidant activity was assessed using the thiobarbituric acid reactive substance (TBARS) assay. Interestingly, cinnamamides with longer alkoxy groups on the C-3 and C-5 positions display enhanced inhibition, and most of the compounds in the series tested exhibit excellent lipid peroxidation inhibitory activities. Some cinamamides bearing hexyloxy or 2,6-di-tert-butyl-4-methyl phenol groups have submicromolar inhibitory activities.
Method of preparing 4-(α-hydrocarbyl-α-cyanomethyl)2,6-di-substituted phenols
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, (2008/06/13)
4-(α-hydrocarbyl-α-cyanomethyl)2,6-di-hydrocarbyl-substituted phenols having the formula STR1 wherein R1 and R2 are the same or different monovalent substituents selected from the group consisting of alkyl, aralkyl and cyclic alkyl radicals and R3 is selected from hydrogen, hydrocarbyl radicals, substituted hydrocarbyl radicals and hydrocarbyloxy radicals are prepared by reacting an N,N-di-hydrocarbyl-4-(α-hydrocarbyl-α-aminomethyl)2,6-di-hydrocarbyl-substituted phenol having the formula STR2 wherein R1, R2 and R3 are as defined above and R4 and R5 are the same or different and are selected from hydrogen, hydrocarbyl radicals and substituted hydrocarbyl radicals with an alkali metal cyanide or an alkaline earth metal cyanide in a suitable solvent. The 4-(α-hydrocarbyl-α-cyanomethyl)2,6-di-substituted phenol thus formed can readily be converted to the corresponding 4-(α-hydrocarbyl-α-cyanomethyl)phenol by dealkylating the substituent groups ortho to the hydroxyl group from the 4-(α-hydrocarbyl-α-cyanomethyl)2,6-di-substituted phenol which then can be converted on hydrolysis to the corresponding α-hydrocarbyl-4-hydroxyphenylacetic acid. These acids have utility as insecticidal and acaricidal intermediates and are deemed to have utility as insecticides themselves as are the 4-(α-hydrocarbyl-α-cyanomethyl)2,6-di-substituted phenols of the present invention.
Preparation of 4-(α-hydrocarbyl-α-cyanomethyl)-2,6-di-substituted phenols
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, (2008/06/13)
4-(α-hydrocarbyl-α-cyanomethyl)2,6-di-substituted phenols having the formula STR1 wherein R1 and R2 are the same or different monovalent substituents selected from the group consisting of alkyl, aralkyl and cyclic alkyl radicals and R3 is selected from hydrogen, hydrocarbyl radicals, substituted hydrocarbyl radicals and hydrocarbyloxy radicals are prepared by reacting a 4-(α-hydrocarbyl-α-hydrocarbyloxymethyl)2,6-di-substituted phenol having the formula STR2 wherein R1, R2 and R3 are as defined above and R4 is selected from hydrocarbyl radicals or substituted hydrocarbyl radicals with an alkali metal cyanide or an alkaline earth metal cyanide in a suitable solvent. The 4-(α-hydrocarbyl-α-cyanomethyl)2,6-di-substituted phenol thus formed can readily be converted to the corresponding 4-(α-hydrocarbyl-α-cyanomethyl)phenol by dealkylating the substituent groups ortho to the hydroxyl group from the 4-(α-hydrocarbyl-α-cyanomethyl)2,6-di-substituted phenol which then can be converted on hydrolysis to the corresponding α-hydrocarbyl-4-hydroxyphenylacetic acid. These acids have utility as insecticidal and acaricidal intermediates and are deemed to have utility as insecticides themselves as are the 4-(α-hydrocarbyl-α-cyanomethyl)2,6-di-substituted phenols of the present invention.
Electrochemical Oxidation, VII. Synthesis and Structure of 7-tert-Butyl-2-methylbenzoxazoles
Dreher, Eberhard-Ludwig,Bracht, Juergen,El-Mobayed, Medhat,Huetter, Peter,Winter, Werner,Rieker, Anton
, p. 288 - 308 (2007/10/02)
Anodic oxidation of 15 tert-butylphenols 1a - o in absolute acetonitrile or acetonitrile/perchloric acid leads to the corresponding 7-tert-butyl-2-methylbenzoxazoles 3a - o.The proof of the structure was achieved by independent synthesis of 3k, and by 13C NMR spectroscopy as well as by X-ray analysis of 7-tert-butyl-2-methyl-5-benzoxazolecarbaldehyde (3j).The influence of the supporting electrolyte on the formation of the oxidation products is discussed.