5594-02-5Relevant academic research and scientific papers
Photoinduced Irreversible Intramolecular Proton Transfer of Arnebinones B, D, and E: The Case of Photoenolization at the p-Benzoquinone-CH2/CH-πSystem
Yan, Hai-Wei,Yang, Ya-Nan,Yuan, Xiang,Zhang, Pei-Cheng,Zhang, Xu,Zhao, Ling-Hao
supporting information, p. 2981 - 2989 (2021/12/02)
Arnebinones B, E, and D (1-3) have been found to be sensitive to light, generating complex and diverse proton transfer products when triggered by light. A unique two-step irreversible intramolecular proton transfer of 1 produced five scalemic mixtures, of
Catalytic Electrophilic Alkylation of p-Quinones through a Redox Chain Reaction
Xu, Xiao-Long,Li, Zhi
, p. 8196 - 8200 (2017/06/30)
Allylation and benzylation of p-quinones was achieved through an unusual redox chain reaction. Mechanistic studies suggest that the existence of trace hydroquinone initiates a redox chain reaction that consists of a Lewis acid catalyzed Friedel–Crafts alkylation and a subsequent redox equilibrium that regenerates hydroquinone. The electrophiles could be various allylic and benzylic esters. The addition of Hantzsch ester as an initiator improves the efficiency of the reaction.
Avarol derivatives as competitive AChE inhibitors, non hepatotoxic and neuroprotective agents for Alzheimer's disease
Tommonaro, Giuseppina,García-Font, Nuria,Vitale, Rosa Maria,Pejin, Boris,Iodice, Carmine,Ca?adas, Sixta,Marco-Contelles, José,Oset-Gasque, María Jesús
, p. 326 - 338 (2016/07/07)
Avarol is a marine sesquiterpenoid hydroquinone, previously isolated from the marine sponge Dysidea avara Schmidt (Dictyoceratida), with antiinflammatory, antitumor, antioxidant, antiplatelet, anti-HIV, and antipsoriatic effects. Recent findings indicate
Oxidation of hydroquinones to benzoquinones with hydrogen peroxide using catalytic amount of silver oxide under batch and continuous-flow conditions
Derikvand, Fatemeh,Bigi, Franca,Maggi, Raimondo,Piscopo, Calogero Giancarlo,Sartori, Giovanni
experimental part, p. 99 - 103 (2010/06/17)
Silver oxide (Ag2O) can be utilized as heterogeneous catalyst in the oxidation of hydroquinones to the corresponding benzoquinones with 30% aq. H2O2. The catalytic properties of Ag2O have been explored in the model reaction of methylhydroquinone with H2O2 performed under batch conditions. Results show that the reaction can be carried out in high yield and selectivity at room temperature under environmentally friendly conditions. The truly heterogeneous catalyst can be recovered by filtration and reused for at least five times, giving the same excellent results (～95% yield, ～98% selectivity). The catalyst can be packed in a tubular reactor and utilized under continuous-flow conditions giving similar good results.
Total synthesis of the novel antifungal agent (±)-jesterone
Mehta, Goverdhan,Pan, Subhas Chandra
, p. 811 - 813 (2007/10/03)
A total synthesis of the novel, biologically active epoxyquinone natural product (±)-jesterone has been accomplished from the readily accessible Diels-Alder adduct of cyclopentadiene and prenylated-p-benzoquinone. The approach delineated here is notable f
Total synthesis of polyprenylhydroquinols and benzoquinones
Bouzbouz, Samir,Kirschleger, Bernard,Villieras, Jean
, p. 67 - 84 (2007/10/03)
The total synthesis of polyprenylhydroquinols and benzoquinones is described.First, two appropriate aromatic allyl carbonates (moieties with one and two prenyls) and two activated bifunctional terpenyl derivatives (moieties with two and three prenyls) were synthesized.These molecules were then reacted together using a highly regio- and stereoselective coupling with Pd(PPh3)4 as a catalyst.The synthesis was achieved by functional group elimination and formation of quinonic and hydroquinonic moieties. - Keywords: polyprenylbenzoquinol; polyprenylhydroquinone; allylcarbonate; ?-allyl palladium complex
Synthesis of Prenylated Quinones by the Oxydative Degradation Approach. Birch vs Vinylogous Birch Hydrogenolysis (BIHY vs VIBIHY) in Controlling Δ2 Stereochemistry of the Prenyl Chain
Ballester, Pablo,Capo, Magdalena,Garcias, Xavier,Saa, Jose M.
, p. 328 - 334 (2007/10/02)
Two novel approaches toward prenylated quinones are described.The first (route A) involves the following three basic operations: (a) construction of a 4-hydroxybenzylamine carrying a tertiary allyl alcohol (cinnamyl alcohol) side chain of appropriate leng
Allylation of quinones bu allylic indium reagents
Araki, Shuki,Katsumura, Nobuhito,Butsugan, Yasuo
, p. 7 - 24 (2007/10/02)
Allylation of a variety of quinones by allylic indium sesquihalides was studied.Reactions of unsubstituted p-benzoquinone with allylindium, prenylindium, and geranylindium reagents gave, after oxidation with silver oxide, the corresponding allylated quinones in good yields.These reactions appear to proceed via 1,2-addition of the allylic indium reagents at the γ-carbon followed by sigmatropic rearrangement.Substituted quinones reacted with allylindium reagent giving excellent yields of allylquinols, whereas with prenylindium and geranylindium reagents, trisubstituted quinones gave diprenylcyclohexene-1,4-diones and 2,3-disubstituted quinones gave mixtures of prnylhydroquinones and diprenylcyclohexene-1,4-diones.In the prenylation of haloquinones, 1,2-addition, sigmatropic rearrangement, and elimination of indium(III) halide occurred in sequence yielding prenylquinones. 2-Hydroxy- and 2-methoxy-1,4-naphthoquinones gave α-addition products with prenylindium and cinnamylindium reagents.
Prenylation of Quinonoid Compounds with Prenyl Bromide Using Lead Bromide/Aluminium Powder as Catalyst
Khanna, R.N.,Singh, Prem Kumar
, p. 1743 - 1749 (2007/10/02)
An efficient method for the prenylation at quinonoid position using prenyl bromide in the presence of catalytic amount of lead bromide and aluminium powder in acetonitrile has been carried out.
