57749-82-3

Upstream product

• 106-44-5 p-cresol 
• 23438-23-5 4-hydroxy-4-methyl-cyclohexa-2,5-dienone 
• 120-12-7 anthracene 
• 142-29-0 cyclopentene 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 23438-23-5 4-hydroxy-4-methyl-cyclohexa-2,5-dienone 
• 109613-02-7 5-hydroxy-5-methyl-7-oxabicyclo<4.1.0>hept-3-en-2-one 
• 1393526-57-2 (3S,4aS,8aR)-8a-methyl-3-phenethyl-4a,5-dihydrobenzo[e][1,2,4]trioxin-6(8aH)-one 
• 1393526-61-8 (3S,4aS,8aR)-3-(3-chloropropyl)-8a-methyl-4a,5-dihydrobenzo[e][1,2,4]trioxin-6(8aH)-one 
• 1393526-59-4 (3S,4aS,8aR)-3-benzyl-8a-methyl-4a,5-dihydrobenzo[e][1,2,4]trioxin-6(8aH)-one 
• 1393526-51-6 (3S,4aS,8aR)-3-cyclohexyl-8a-methyl-4a,5-dihydrobenzo[e][1,2,4]trioxin-6(8aH)-one 

Relevant academic research and scientific papers

Newer series of trioxane derivatives as potent antimalarial agents

Among synthesized 1,2,4-trioxane derivatives, six compounds were found to be considerably potent, with better activity against resistant strain of P. falciparum than the sensitive strain. The IC50 values of the best compound with 4-hydroxypheny

Novel series of 1,2,4-trioxane derivatives as antimalarial agents

Among three series of 1,2,4-trioxane derivatives, five compounds showed good in vitro antimalarial activity, three compounds of which exhibited better activity against P. falciparum resistant (RKL9) strain than the sensitive (3D7) one. Two best compounds

Multigram Synthesis of Trioxanes Enabled by a Supercritical CO2Integrated Flow Process

Photochemical synthesis of highly reactive hydroperoxides and their conversion into useful products, such as 1,2,4-trioxanes, are of wide interest for synthetic organic chemistry and pharmaceutical manufacturing particularly because of their relevance as potential antimalarial and anticancer treatment drugs, for example, Artemisinin. One class of antimalarial drugs is based on 1,2,4-trioxane scaffolds although production of such compounds on a gram scale is challenging due to their instability in oxidizable solvents. Furthermore, current methods employ either solid oxidants, which make continuous processing problematic, or molecular oxygen, requiring long reaction times of up to 48 h. Here, we report a new multigram continuous approach using a custom-built high-pressure sapphire photoreactor to synthesize trioxanes via the dearomatization of para-substituted phenols by photogenerated singlet oxygen in supercritical CO2. CO2 also facilitates mixing with O2 and has lower viscosity, thereby improving penetration into the pores of the solid acid catalyst used for the formation of trioxanes. We show the capabilities of a 5.2 mL reactor to scale up the reaction to 67 g/day. This synthetic approach provides a platform to rapidly access high-value compounds under flow conditions, with high atom efficiencies, excellent yields, short reaction times, and without the need for isolation of hazardous intermediates.

Photocatalytic Activity of Ruthenium(II) Complex with 1,10-Phenanthroline-3,8-dicarboxylic Acid in Aerobic Oxidation Reactions

Abstract: Mixed-ligand ruthenium(II) complex with 2,2′-bipyridine and 1,10-phenanthroline-3,8-dicarboxylic acid with the composition [Ru(phen-C)(bpy)2]Cl2·5H2O (bpy = 2,2′-bipyridine, phen-C = 1,10-phenantroline-3,8-dicarboxylic acid) has been synthesized and characterized by spectral data. The complex has been tested as photocatalyst in aerobic oxidation reactions, including transformation of arylboronic acids to phenols, primary amines to imines, and sulfides to sulfoxides in aqueous medium. The possibility of regeneration of the catalyst in the oxidation of sulfides has been demonstrated.

Substrate-Selectivity in Catalytic Photooxygenation Processes Using a Quinine-BODIPY System

Substrate selectivity by means of synthetic catalysts remains a challenging topic in chemistry. Here, a catalytic system combining an iodo-BODIPY photosensitizer and quinine was evaluated in the competitive photooxygenation of non-hydrogen and hydrogen-bond-donor substrates. The ability of quinine to activate hydrogen-bond-donor substrates towards photooxygenation was reported and the results were benchmarked with photooxygenation experiments in the absence of quinine.

An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Bronsted acid catalysis cascade

The desymmetrization of p-peroxyquinols using a Bronsted acid-catalyzed acetalization/oxa-Michael cascade was achieved in high yields and selectivities for a variety of aliphatic and aryl aldehydes. Mechanistic studies suggest that the reaction proceeds through a dynamic kinetic resolution of the peroxy hemiacetal intermediate. The resulting 1,2,4-trioxane products were derivatized and show potent cancer cell-growth inhibition.

Oxidative de-aromatization of para-alkyl phenols into para-peroxyquinols and para-quinols mediated by oxone as a source of singlet oxygen

(Chemical Equation Presented) Easy does it: Easily handled and environmentally safe oxone generates singlet oxygen which effects the simple and selective oxidative de-aromatization of para-alkyl phenols 1 into para-peroxyquinols 2 under very mild conditions with good to excellent yields. A one-pot access to para-quinols 3 from 1 is also possible after treatment of the crude reaction mixture with sodium thiosulfate.

BIOGENESIS-LIKE TRANSFORMATION OF SALIDROSIDE TO RENGYOL AND ITS RELATED CYCLOHEXYLETANOIDS OF FORSYTHIA SUSPENSA

Photooxygenation of salidroside (8) in methanol in presence of Rose Bengal afforded cornoside (9), which, on high pressure hydrogenation with 5percent palladium on activated carbon, yielded rengyoside B (6).Reduction of 6 with sodium borohydride gave rengyoside A(5) stereoselectively.By enzymatic hydrolysis, 9, 6 and 5 furnished rengyolone (4), rengyoxide (3) and rengyol (1), respectively. Similerly, p-hydroxyphenylethanol (10), the aglycone part of salidroside (8), was oxygenated photochemically to a dienone alcohol, which cyclized spontaneously to rengyolone (4).Hallerone (17) was obtained by the photooxygenation of p-hydroxyphenylethyl acetate (10b).Thus the plausible biosynthetic routes from salidroside (8) to rengyol (1) and the related natural cyclohexylethanoids were simulated chemically.

Quinol Epoxides from p-Cresol and Estrone by Photooxygenation and Titanium(IV)- or Vanadium(V)-Catalyzed Oxygen Transfer

On treatment with Ti(OiPr)4, 4-hydroperoxy-4-methyl-2,5-cyclohexadien-1-one (1) and 10β-hydroperoxy-1,4-estradiene-3,17-dione (3), readily available by photooxygenation of p-cresol and estrone, respectively, were converted to the corresponding epoxyquinol

THE FLUORIDE ION EFFECT IN THE REACTIONS OF SINGLET OXYGEN WITH ENOLS

The fluoride ion effect in the reaction of enolic systems with singlet oxygen has been investigated. β-Dicarbonyl compounds yielded 1,2,3-tricarbonyl derivatives, some of which underwent further hydration, whereas α-diketones suffered oxidative decarboxylation to give open-chain aldehydo-acids or keto-acids.