- Molecular structure of PhOCH2CH(OH)CH2OPH
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The molecular structure of PhOCH2CH(OH)CH2OPh has been determined. The C - O -C - C - C - O - C backbone adopts an anti-anti-anti-anti conformation. Inter-molecular O - H ... O hydrogen-bonding results in dimeric units which stack into zig-zag tapes. Crystal data: orthorhombic, Pbca, a = 10.383(1), b = 8.0532(0), c = 31.295(3) A, V = 2616.8(3) A3, and Z = 8.
- Koide, Yoshihiro,Bott, Simon G.,Barron, Andrew R.
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- Full atom-efficiency transformation of wasted polycarbonates into epoxy thermosets and the catalyst-free degradation of the thermosets for environmental sustainability
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We report two sustainable features in this work. The first feature is that we successfully applied wasted polycarbonate (WPC) as an epoxy curing agent for epoxy resins to prepare WPC-cured epoxy thermosets. The curing of WPC and epoxy is based on the reaction of a carbonate and an epoxide, which is proven by a model reaction of diphenyl carbonate (DPC) and glycidyl phenyl ether (GPE) in the presence of a catalytic amount of 4-dimethylaminopyridine (DMAP). The WPC-cured epoxy thermosets show comparable thermal properties to commercial-based, phenol novolac (PN)-cured epoxy thermosets. Interestingly, the films of WPC-cured epoxy thermosets are foldable, while those of PN-cured epoxy thermosets are brittle, demonstrating the advantage of using WPC as a curing agent over PN. Since the WPC was used directly without any digestion or pyrolysis process, the atomic efficiency is 100percent, making this WPC recycling strategy economically attractive. The second feature is that we successfully degraded the WPC-cured epoxy thermosets to phenoxy resins through a catalyst-free aminolysis process, that is, the products based on the WPC-cured epoxy thermosets are degradable when their lifespans are expired. The transformation of WPC into epoxy thermosets, along with the degradation of the epoxy thermosets, makes this work attractive for sustainability.
- Abu-Omar, Mahdi M.,Chan, Jian Ren,Chen, Chien Han,Juang, Tzong Yuan,Lin, Ching Hsuan,Shao, Shih Wei
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p. 4683 - 4696
(2020/08/10)
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- An innovative synthesis pathway to benzodioxanes: The peculiar reactivity of glycerol carbonate and catechol
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A peculiar reactivity of glycerol carbonate (GlyC) as an innovative and highly reactive alkylating agent for phenolic compounds is investigated in this article. In particular, 2-hydroxymethyl-1,4-benzodioxane (HMB), a key intermediate for the pharmaceutical industry, has been selectively synthesized by the reaction of a slight excess of GlyC with catechol in the presence of a basic catalyst (NaOCH3, Na-mordenite, MgO), without requiring a reaction solvent. Both reagents have been quantitatively converted in just one hour at 170 °C with a HMB yield, up to 88%, in the presence of a homogeneous basic catalyst (NaOCH3). Notably, the main side product, the HMB isomer, may be an interesting intermediate for the synthesis of calone analogues, which are important scaffolds used in fragrances. A detailed mechanistic study, supported by kinetics, GC-MS, and HMBC NMR characterization, is also reported. Accordingly, this paper describes a completely innovative and greener synthesis pathway to benzodioxanes.
- Tabanelli,Giliberti,Mazzoni,Cucciniello,Cavani
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p. 329 - 338
(2019/01/28)
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- Synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines
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We describe herein the antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines, prepared in four simple steps from epichlorohydrin. Among the evaluated compounds, three (4o, 4q, and 4r) displayed considerable activity against Leishmania amazonensis promastigote forms, with IC50 values below 10 μM. We also analyzed the effects of the nature and the position of ring substituent on activity. Two amines (4m and 4o) showed excellent profiles in the treatment of L. amazonensis-infected macrophages, reducing the parasite burden by more than 95% in tested concentrations.
- Lavorato, Stefania N.,Duarte, Mariana C.,Lage, Daniela P.,Tavares, Carlos A. P.,Coelho, Eduardo A. F.,Alves, Ricardo J.
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p. 1052 - 1072
(2017/04/14)
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- 1,3-Bis(aryloxy)propan-2-ols as potential antileishmanial agents
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We describe herein the synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-ols. Five compounds (2, 3, 13, 17, and 18) exhibited an effective antileishmanial activity against stationary promastigote forms of Leishmania amazonensis (IC50??15.0?μm), and an influence of compound lipophilicity on activity was suggested. Most of the compounds were poorly selective, as they showed toxicity toward murine macrophages, except 17 and 18, which presented good selective indexes (SI?≥?10.0). The five more active compounds (2, 3, 13, 17, and 18) were selected for the treatment of infected macrophages, and all of them were able to reduce the number of internalized parasites by more than 80%, as well as the number of infected macrophages by more than 70% in at least one of the tested concentrations. Altogether, these results demonstrate the potential of these compounds as new hits of antileishmanial agents and open future possibilities for them to be tested in in vivo studies.
- Lavorato, Stefania N.,Duarte, Mariana C.,Lage, Daniela P.,Tavares, Carlos A. P.,Coelho, Eduardo A. F.,Alves, Ricardo J.
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p. 981 - 986
(2017/10/05)
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- New bent-shaped azomethine monomers for optical applications
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It was convenient preparative method of new methacrylic monomers with banana-shaped structure and photoactive azomethine fragments synthesis. To determine the effect of large azomethine fragment on the process of homopolymerization, symmetrical model compounds with simpler structure were synthesized. The kinetic of its thermally initiated radical polymerization in DMF solution was studied and compared with the kinetics of model compounds does not containing bulky photochromic fragment. Peculiarities of photo initiated processes of E,Z-isomerization were studied.
- Ovdenko, Valeriia,Kolendo, Aleksey
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p. 113 - 121
(2016/12/22)
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- Continuous and convergent access to vicinyl amino alcohols
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Five active pharmaceutical ingredients (APIs) containing the vicinyl amino alcohol moiety were synthesized using a convergent chemical assembly system. The continuous system is composed of four flow reaction modules: biphasic oxidation, Corey-Chaykovsky epoxidation, phenol alkylation, and epoxide aminolysis. Judicious choice of reagents and module order allowed for two classes of β-amino alcohols, aryl and aryloxy, to be synthesized in good (27-69%) overall yields.
- Nobuta, Tomoya,Xiao, Guozhi,Ghislieri, Diego,Gilmore, Kerry,Seeberger, Peter H.
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supporting information
p. 15133 - 15136
(2015/10/12)
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- Synthesis, characterization and catalytic activity of novel large network polystyrene-immobilized organic bases
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In view of searching for efficient polymeric supports for organic bases to be used in environmentally friendly reaction conditions, novel gel-type cross-linked polystyrenes functionalized with diethylamine and 1,5,7-triazabicyclo[4.4.0]dec-5-ene, have been prepared. The structural properties and morphology of these catalysts have been determined by extensive solid state NMR experiments, FTIR spectroscopy and SEM/TEM microscopy. SPACeR-supported bases were found to exhibit high catalytic activity in the epoxide ring opening by phenols. A range of β-substituted alcohols have been readily and regioselectively synthesized.
- Tassi, Marco,Bartollini, Elena,Adriaensens, Peter,Bianchi, Luca,Barkakaty, Balaka,Carleer, Robert,Chen, Jihua,Hensley, Dale K.,Marrocchi, Assunta,Vaccaro, Luigi
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p. 107200 - 107208
(2016/01/08)
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- Monovalent mannose-based DC-SIGN antagonists: Targeting the hydrophobic groove of the receptor
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Dendritic cell-specific, intercellular adhesion molecule-3-grabbing non-integrin (DC-SIGN) is a C-type lectin expressed specifically on dendritic cells. It is a primary site for recognition and binding of various pathogens and thus a promising therapeutic target for inhibition of pathogen entry and subsequent prevention of immune defense cell infection. We report the design and synthesis of d-mannose-based DC-SIGN antagonists bearing diaryl substituted 1,3-diaminopropanol or glycerol moieties incorporated to target the hydrophobic groove of the receptor. The designed glycomimetics were evaluated by in vitro assay of the isolated DC-SIGN extracellular domain for their ability to compete with HIV-1 gp120 for binding to the DC-SIGN carbohydrate recognition domain. Compounds 14d and 14e, that display IC50 values of 40 μM and 50 μM, are among the most potent monovalent DC-SIGN antagonists reported. The antagonistic effect of all the synthesized compounds was further evaluated by a one-point in vitro assay that measures DC adhesion. Compounds 14d, 14e, 18d and 18e were shown to act as functional antagonists of DC-SIGN-mediated DC adhesion. The binding mode of 14d was also studied by molecular docking and molecular dynamics simulation, which revealed flexibility of 14d in the binding site and provides a basis for further optimization.
- Toma?i?, Tihomir,Haj?ek, David,?vajger, Urban,Luzar, Jernej,Obermajer, Nata?a,Petit-Haertlein, Isabelle,Fieschi, Franck,Anderluh, Marko
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p. 308 - 326
(2014/03/21)
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- One-pot synthesis of aryloxypropanediols from glycerol: Towards valuable chemicals from renewable sources
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Glycerol offers an easy and green route for the synthesis of aryloxypropanediols of known pharmacological activity. Glycerol is selectively converted to aryloxypropanediols in a one-pot reaction, through in situ formed glycerol carbonate, under benign and solvent-free conditions. Catalyst and unreacted reagent can be recycled.
- Truscello, Ada M.,Gambarotti, Cristian,Lauria, Mirvana,Auricchio, Sergio,Leonardi, Gabriella,Shisodia, Suresh U.,Citterio, Attilio
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p. 625 - 628
(2013/03/29)
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- Synergistic dual activation catalysis by palladium nanoparticles for epoxide ring opening with phenols
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Synergistic dual activation catalysis has been devised for epoxide phenolysis wherein palladium nanoparticles induce electrophilic activation via coordination with the epoxide oxygen followed by nucleophilic activation through anion-π interaction with the aromatic ring of the phenol, and water (reaction medium) also renders assistance through 'epoxide-phenol' dual activation.
- Seth, Kapileswar,Roy, Sudipta Raha,Pipaliya, Bhavin V.,Chakraborti, Asit K.
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supporting information
p. 5886 - 5888
(2013/07/25)
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- An efficient catalyst for ring opening of epoxides with phenol and thiophenol under solvent-free conditions
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An efficient and rapid procedure for ring opening reaction of various epoxides with phenol and thiophenol derivatives was developed. The procedure can be obtained at room temperature under solvent-free condition in presence of (C4H12N2)2[BiCl6] Cl·H2O (1 mol %). This catalyst can be reused several times without significant loss of activity.
- Lu, Hong-Fei,Zhou, Jun-Tao,Cheng, He-Long,Sun, Lei-Lei,Yang, Fei-Fei,Wu, Run-Ze,Gao, Yu-Hua,Luo, Zhi-Bin
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p. 11174 - 11184
(2014/01/06)
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- Rasta resin as support for TBD in base-catalyzed organic processes
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Although its intriguing features, such as uniform functionalization through the entire beads and a very high-loading capacity are suitable candidates for solid-phase synthesis and reagent-scavenging, the use of Rasta resin as support for organocatalysis has been little explored. In this contribution, Rasta polymer has been used to preparation of high-loading Rasta-TBD. This catalyst has been able to efficiently promote several organic transformations with constantly good and promising results.
- Bonollo, Simona,Lanari, Daniela,Angelini, Tommaso,Pizzo, Ferdinando,Marrocchi, Assunta,Vaccaro, Luigi
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scheme or table
p. 216 - 222
(2012/03/08)
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- Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: Application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols
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An enantioselective borane-mediated reduction of a variety of 2-haloketones with 10% spiroaminoborate ester 1 as catalyst is described. By a simple basic workup of 2-halohydrins, optically active epoxides are obtained in high yield and with excellent enantiopurity (up to 99% ee). Ring-opening of oxiranes with phenoxides or sodium azide is investigated under different reaction conditions affording nonracemic 1,2-hydroxy ethers and 1,2-azido alcohols with excellent enantioselectivity (99% ee) and in good to high chemical yield. 2011 American Chemical Society.
- Huang, Kun,Wang, Haiyang,Stepanenko, Viatcheslav,De Jesus, Melvin,Torruellas, Carilyn,Correa, Wildeliz,Ortiz-Marciales, Margarita
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supporting information; scheme or table
p. 1883 - 1886
(2011/06/20)
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- 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2- diazaphosphorine supported on polystyrene (PS-BEMP) as an efficient recoverable and reusable catalyst for the phenolysis of epoxides under solvent-free conditions
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2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3, 2-diazaphosphorine supported on polystyrene (PS-BEMP) is an efficient catalyst for the ring-opening of epoxides with phenols (1.0 equiv.). Excellent yields have been obtained and in most of the cases the final products have been isolated in pure form without any additional purification step. E-factors associated to this protocol are small and further improvements were obtained by setting a cyclic continuous-flow reactor operating under solvent-free conditions (SolFC) that allowed us to minimize waste and reduce the E-factor by 95% compared to batch conditions. In addition the representative synthesis of a 2,3-dihydrobenzo[1,4]dioxepin-5-one has been realized. Optimization of this process was achieved by setting up an automated multi-step continuous-flow reactor based on a phenolysis process and a subsequent lactonization by thermal treatment of the reaction mixture. 3-Phenoxymethyl-2,3-dihydrobenzo[e][1,4] dioxepin-5-one was isolated in pure form and on a multi-gram scale in a very satisfactory 86% overall yield and an E-factor of 1.47.
- Zvagulis, Artis,Bonollo, Simona,Lanari, Daniela,Pizzo, Ferdinando,Vaccaro, Luigi
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supporting information; scheme or table
p. 2489 - 2496
(2010/12/29)
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- Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity
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Direct anti-tuberculosis screening of commercially available compound libraries identified a novel piperidinol with interesting anti-tuberculosis activity and drug like characteristics. To generate a structure activity relationship about this hit a 22 mem
- Sun, Dianqing,Scherman, Michael S.,Jones, Victoria,Hurdle, Julian G.,Woolhiser, Lisa K.,Knudson, Susan E.,Lenaerts, Anne J.,Slayden, Richard A.,McNeil, Michael R.,Lee, Richard E.
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experimental part
p. 3588 - 3594
(2009/10/10)
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- Erbium(III) triflate is a highly efficient catalyst for the synthesis of β-alkoxy alcohols, 1,2-diols and β-hydroxy sulfides by ring opening of epoxides
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Chemo- and stereoselectivity in the ring-opening reaction of epoxides with erbium(III) triflate are described. Epoxides can be cleaved under neutral conditions with alcohols and thiols in the presence of catalytic amounts of Lewis acid, affording the corresponding β-alkoxy alcohols and β-hydroxy sulfides in high yields. In water, epoxide ring opening occurs to produce the corresponding diols in good yields.
- Dalpozzo, Renato,Nardi, Monica,Oliverio, Manuela,Paonessa, Rosina,Procopio, Antonio
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experimental part
p. 3433 - 3438
(2010/02/28)
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- An economical noncatalytic approach to the synthesis of congested diaryl ethers and aryl benzyl thioethers through C-C insertion
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An efficient one-pot synthesis of diaryl ethers and aryl benzyl thioethers has been delineated through base-induced ring transformation of 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles, methyl 6-aryl-4-methylthio- 2H-pyran-2-one-3-carboxylates and 6-aryl-4-(piperidin-1-yl)-2H-pyran-2-one-3- carbonitriles by either 1-phenoxypropan-2-one, 1,3-diphenoxypropan-2-one or 4-arylthiobutan-2-one, under very mild reaction conditions, in excellent yield. Georg Thieme Verlag Stuttgart.
- Farhanullah,Ji Ram, Vishnu
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body text
p. 2265 - 2268
(2009/12/24)
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- An efficient catalyst-free regio- and stereoselective ring-opening of epoxides with phenoxides using polyethylene glycol as the reaction medium
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A catalyst-free regio- and stereoselective ring-opening of epoxides with phenoxides has been carried out efficiently using polyethylene glycol as the reaction medium to form the corresponding β-aryloxyalcohols in high yields at room temperature.
- Das, Biswanath,Krishnaiah, Maddeboina,Thirupathi, Ponnaboina,Laxminarayana, Keetha
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p. 4263 - 4265
(2008/02/12)
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- Bi(OTf)3-catalyzed regioselective ring opening of epoxides with phenols: Facile synthesis of 1,3-diaryloxy-2-propanols
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Substituted aryl oxiranes undergo the facile ring opening with phenols in the presence of catalytic amount of bismuth(III) triflate to afford 1,3-diaryloxy-2-propanols in excellent yields under mild conditions. Bismuth(III) triflate is relatively non-toxic, easy to handle and inexpensive, which makes this procedure particularly attractive for large scale synthesis. Copyright
- Kamal, Ahmed,Ahmed, Syed Kaleem,Sandbhor, Mahendra,Khan, Mohammed Naseer Ahmed,Arifuddin, Mohammed
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p. 1142 - 1143
(2007/10/03)
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- Highly regioselective ring opening of epoxides with polymer supported phenoxide and naphthoxide anions
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Amberlite IRA-400 supported phenoxide and naphthoxide anions are easily prepared. These polymer supported reagents that are highly air stable are used for the regioselective ring opening reactions of different epoxides to give aryl ether alcohols in high yields under mild reaction conditions.
- Tamami,Iranpoor,Rezaei
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p. 2789 - 2795
(2007/10/03)
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- Highly regioselective ring opening of oxiranes with phenoxides in the presence of β-cyclodextrin in water
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Highly regioselective ring opening of oxiranes to β-hydroxy ethers with phenoxides has been achieved in impressive yields in the presence of β-cyclodextrin as catalyst and water as solvent.
- Surendra,Krishnaveni, N. Srilakshmi,Nageswar,Rao, K. Rama
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p. 4994 - 4995
(2007/10/03)
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- Ring opening of epoxides with carboxylates and phenoxides in micellar media catalyzed with Ce(OTf)4
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Efficient ring opening reaction of epoxides with carboxylates and phenoxide anions catalyzed with ceric triflate is performed in micellar media. This new method is a useful procedure for the preparation of β-carboxy and phenoxy alcohols from epoxides under mild reaction conditions.
- Iranpoor,Firouzabadi,Safavi,Shekarriz
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p. 2287 - 2293
(2007/10/03)
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- Complex hydrophobe-containing oligomers
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This invention relates to polymers, especially emulsion polymers, and their use for the thickening of a variety of aqueous systems, to methods of thickening utilizing the polymers, to enhancement of such thickening by the addition of surfactants, solvents or non-solvents, and to other aspects including coating compositions and other aqueous systems thickened with the polymers. This invention also relates to new complex hydrophobe-containing oligomers and their use in producing the polymers of this invention.
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- Complex hydrophobe compounds
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This invention relates to complex hydrophobe compounds and to alkoxylation products, i.e., condensation reaction products of alkylene oxides and complex hydrophobe compounds having at least one active hydrogen. This invention also relates to alkoxylation products that have beneficial, narrow molecular weight ranges.
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- Polysaccharides containing complex hydrophobic groups
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Polysaccharides, including hydroxyethyl cellulose, having complex hydrophobic group substitution, provide latex compositions, such as paints, with improved rheology and stability. Improved processes for producing such polysaccharides are also provided.
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- A novel reaction for the functionalization of epoxy resins: New regio- and chemoselective ring-opening of epoxides with aryl silyl ether catalyzed by cesium fluoride
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By use of cesium fluoride as a catalyst, aryl or alkyl glycidyl ethers were ring-opened by aryl trimethylsilyl ether to produce O-protected aryloxyhydrins with a quantitative regioselectivity for the first time. Alkyl silyl ether was ineffective for this ring-opening.
- Nambu,Endo
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p. 1723 - 1726
(2007/10/02)
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- MECHANISM OF REACTION OF PHENYL GLYCIDYL ETHER WITH PHENYL BENZOATE IN THE PRESENCE OF WATER
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The reaction of phenyl glycidyl ether with phenyl benzoate in the presence of water was investigated by adsorption liquid chromatography.
- Pankratov, V. A.,Frenkel', Ts. M.,Shvorak, A. E.,Komarova, L. I.,Grozdov, A. G.,Maslov, V. A.
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p. 118 - 120
(2007/10/02)
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- Preparation of 1,3-bis(aryloxy)-2-propanols
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Phenoxy resins and other 1,3-bis(aryloxy)-2-propanol compounds are prepared by contacting hydroxy-substituted aromatic compounds with organyl 2-oxo-1,3-dioxolan-4-ylmethyl carbonates.
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- Hypocholesterolemic activity of 1,3 bis(substituted phenoxy) 2 propanones
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A series of 1,3 bis (substituted phenoxy) 2 propanones was found to be active hypocholesterolemic agents at 10 mg/kg/day. The p chloro and p methyl substituted phenoxy compounds possess the highest activity. These compounds did not possess the estrogenic and antifertility activities of the related previously reported derivatives of the bis (β phenylethyl) ketone series. The 1,3 bis (p methylphenoxy) 2 propanone (7) also lowered serum triglycerides and glycerol which appeared to be due to increased levels of serum lipase and reduced activity of liver lipase. There was reduced incorporation of free fatty acids into complex lipids by the liver. Cholesterol was excreted faster in the treated animals.
- Piantadosi,Hall,Wyrick,Ishaq
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p. 222 - 229
(2007/10/12)
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