131236-58-3Relevant academic research and scientific papers
Synthesis, chemical reactivity as michael acceptors, and biological potency of monocyclic cyanoenones, novel and highly potent anti-inflammatory and cytoprotective agents(1)
Zheng, Suqing,Santosh Laxmi,David, Emilie,Dinkova-Kostova, Albena T.,Shiavoni, Katherine H.,Ren, Yanqing,Zheng, Ying,Trevino, Isaac,Bumeister, Ronald,Ojima, Iwao,Wigley, W. Christian,Bliska, James B.,Mierke, Dale F.,Honda, Tadashi
supporting information; experimental part, p. 4837 - 4846 (2012/07/03)
Novel monocyclic cyanoenones examined to date display unique features regarding chemical reactivity as Michael acceptors and biological potency. Remarkably, in some biological assays, the simple structure is more potent than pentacyclic triterpenoids (e.g
Photochemical and Acid-Catalyzed Dienone-Phenol Rearrangements. The Effect of Substitutents on the Regioselectivity of 1,4-Sigmatropic Rearrangements of the Type A Intermediate
Schultz, Arthur G.,Hardinger, Steven A.
, p. 1105 - 1111 (2007/10/02)
Birch reduction of isophthalic acid and 3-cyanobenzoic acid followed by (1) methylation of the resulting enolate with methyl iodide and (2) esterification with diazomethane proved 2-carbomethoxy- and 2-cyano-6-methyl-6-carbomethoxy-1,4-cyclohexadienes 9 and 25.Type A photorearrangement of a series of 2-carbomethoxy-, 2-cyano-, 2-methoxy-, and 2-methyl-4-carbomethoxy-4-methyl-2,5-cyclohexadien-1-ones 11, 26, 45a, and 45b gave 4-carbomethoxy-3-methyl-2-substituted-phenols 12, 28, 46, and 31.It has been demonstrated that the regioselectivity of type A photorearrangement of C(2) substituted 2,5-cyclohexadien-1-ones is governed by electronic rather than steric effects to give the intermediate C(1) rather than C(3) substituted bicyclo1,5>hex-3-en-2-ones.Regioselectivities of the acid-catalyzed dienone-phenol rearrangements of C(2) substituted 2,5-cyclohexadienones 11, 45a, and 45b appear to be dependent upon the relative stabilities of carbocations resulting from migration of the C(4) carbomethoxy group.
