- Rational design 2-hydroxypropylphosphonium salts as cancer cell mitochondria-targeted vectors: Synthesis, structure, and biological properties
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It has been shown for a wide range of epoxy compounds that their interaction with triphenylphosphonium triflate occurs with a high chemoselectivity and leads to the formation of (2-hydroxypropyl)triphenylphosphonium triflates 3 substituted in the 3-position with an alkoxy, alkylcarboxyl group, or halogen, which were isolated in a high yield. Using the methodology for the disclosure of epichlorohydrin with alcohols in the presence of boron trifluoride ether-ate, followed by the substitution of iodine for chlorine and treatment with triphenylphosphine, 2-hydroxypropyltriphenylphosphonium iodides 4 were also obtained. The molecular and supramolec-ular structure of the obtained phosphonium salts was established, and their high antitumor activity was revealed in relation to duodenal adenocarcinoma. The formation of liposomal systems based on phosphonium salt 3 and L-α-phosphatidylcholine (PC) was employed for improving the bioavailabil-ity and reducing the toxicity. They were produced by the thin film rehydration method and exhibited cytotoxic properties. This rational design of phosphonium salts 3 and 4 has promising potential of new vectors for targeted delivery into mitochondria of tumor cells.
- Amerhanova, Syumbelya K.,Dimukhametov, Mudaris N.,Gubaidullin, Aidar T.,Islamov, Daut R.,Litvinov, Igor A.,Lyubina, Anna P.,Mironov, Vladimir F.,Nemtarev, Andrey V.,Pashirova, Tatiana N.,Titov, Eugenii A.,Tsepaeva, Olga V.,Voloshina, Alexandra D.
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- A phosphonium ylide as a visible light organophotoredox catalyst
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A phosphonium ylide-based visible light organophotoredox catalyst has been designed and successfully applied to halohydrin synthesis using trichloroacetonitrile and epoxides. An oxidative quenching cycle by the ylide catalyst was established, which was confirmed by experimental mechanistic studies.
- Toda, Yasunori,Tanaka, Katsumi,Matsuda, Riki,Sakamoto, Tomoyuki,Katsumi, Shiho,Shimizu, Masahiro,Ito, Fuyuki,Suga, Hiroyuki
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supporting information
p. 3591 - 3594
(2021/04/14)
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- 1,3,2,4-diazadiphosphetidine-based phosphazane oligomers as source of P(III) atom economy reagents: Conversion of epoxides to vic -haloalcohols, vic -dihalides, and alkenes in the presence of halogen sources
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1,3,2,4-Diazadiphosphetidines (P1-P3), as easily prepared, stable, and heterogeneous P(III) compounds, were used for the efficient conversion of epoxides to vic-halohydrins, vic-dihalides, or alkenes in the presence of different halogen sources in CH3CN. Of these phosphazanes, P3 is most suitable and contains 4 phosphorous atoms with the advantage of having greater atom economy and its phosphorus oxide byproduct can be easily separated from the reaction mixture by simple filtration. The nitrogen atoms in this molecule can also act as acid scavengers in the reaction.
- Iranpoor, Nasser,Firouzabadi, Habib,Etemadidavan, Elham
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p. 1165 - 1173
(2014/10/16)
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- Ionic telomerization of 1-chloro-2,3-epoxypropane with allyl alcohol and properties of products obtained
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Ionic telomerization of 1-chloro-2,3-epoxypropane with allyl alcohol in the presence of boron trifluoride etherate as a route to halogenated epoxy oligoethers was studied. Selective chlorination or bromination of the intermediate oligo(chlorohydrin), followed by dehydrochlorination (epoxidation) of the intermediate oligohalohydrins with NaOH, was performed. The synthesized products are effi cient as active diluents for a compound based on ED-20 resin.
- Kerimov,Orudzheva,Mamedova,Alieva
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p. 1364 - 1369
(2014/01/06)
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- Facile, high regio- And chemoselective conversion of epoxides to β-chlorohydrins using chlorodiphenylphosphine under solvent-free conditions
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A new method is described for the mild and high regioselective conversion of epoxides to β-chlcrohydrins in high yields even in the presence of alcohols, carboxylic acids, oximes, amides, thiols and tetrahydropyranyl ethers using chlorodiphenylphosphine (ClPPh2) under solvent-free and neutral conditions at room temperature and in short reaction times. In addition, some other functional groups such as carbon-carbon double bonds, ester groups and also phenyl ring that are present in the epoxide molecules remain intact in this method.
- Aghapour, Ghasem,Afzali, Asieh,Salek, Fahimeh
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experimental part
p. 231 - 236
(2009/12/03)
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- Silphos [PCl3-n (SiO2)n]: A heterogeneous phosphine reagent for the regioselective synthesis of vic-haloalcohols
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Silphos as a silica-based phosphine [PCl3-n (SiO 2)n] provides a practical method for the conversion of epoxides to vic-haloalcohols in the presence of molecular bromine, iodine, or N-halosuccinimides (NXS, X = Cl, Br, I) in CH3CN or under solvent-free conditions at r.t. The simple filtration of heterogeneous Silphos oxide from the reaction mixture affords the pure vic-haloalcohols with excellent yields. Copyright Taylor & Francis Group, LLC.
- Iranpoor, Nasser,Firouzabadi, Habib,Jamalian, Arezu
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p. 2615 - 2621
(2007/10/03)
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- Regioselective synthesis of vic-halo alcohols and symmetrical or unsymmetrical vic-dihalides from epoxides using triphenylphosphine -N-halo imides
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A simple, novel, and highly regioselective cleavage of epoxides into vicinal halo alcohols and symmetrical or unsymmetrical dihalides is described using different stoichiometries of triphenylphosphine (PPh3) and N-halo succinimide (NXS) or N-halo saccharine (NXSac).
- Iranpoor, Nasser,Firouzabadi, Habib,Azadi, Roya,Ebrahimzadeh, Farzaneh
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- Carbon tetrabromide: An efficient catalyst for regioselective ring opening of epoxides with alcohols and water
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Epoxides undergo rapid ring opening with a range of alcohols in the presence of catalytic amount of carbon tetrabromide under mild and convenient conditions to afford the corresponding β-alkoxy alcohols and 1,2-diols in high yields with high regioselectivity. Georg Thieme Verlag Stuttgart.
- Yadav,Reddy,Harikishan,Madan,Narsaiah
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p. 2897 - 2900
(2007/10/03)
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- Silica sulfuric acid; an efficient and reusable catalyst for regioselective ring opening of epoxides by alcohols and water
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The nucleophilic ring opening reactions of epoxides by aliphatic alcohols and water are achieved efficiently in the presence of catalytic amounts of silica sulfuric acid with high degree of regioselectivity. The catalyst is reusable and can be applied several times without any decrease in the yield of reactions.
- Salehi, Peyman,Dabiri, Minoo,Zolfigol, Mohammad Ali,Fard, Mohammad Ali Bodaghi
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p. 1113 - 1121
(2007/10/03)
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- Difluorocarbene induced of facile synthesis of chlorohydrins from glycidyl ethers
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A novel and unusual approach based on a ClCF2COONa-DMF system has been developed for the synthesis of chlorohydrins via an unexpected mechanism. In a first ever report for the synthesis of chlorohydrins from glycidyl ethers, e.g., CH2=CH-CH2-O-Z, CH 3CH2-O-Z, C6H5-O-Z, C 6H4(o-CH3)-O-Z, CH2=C(CH 3)C(=O)-O-Z, etc., (where Z = glycidyl), difluorocarbene-induced facile regioselective ring opening of epoxides has generated the compound in high yield (70%-83%).
- Singh, Sapna,Bhadury, Pinaki S.,Sharma, Mamta,Palit, Meehir,Jaiswal, Devendra K.
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p. 1249 - 1253
(2007/10/03)
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- Magnesium hydrogensulfate: A cheap and efficient catalyst for the conversion of epoxides into β-alkoxy alcohols, vicinal-diols, and thiiranes
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The nucleophilic ring opening reactions of epoxides by aliphatic alcohols and water are achieved efficiently in the presence of catalytic amounts of magnesium hydrogensulfate, Mg(HSO4)2, with high degree of regioselectivity. The reactions are chemoselective and many of the other functional groups such as ethereal carbon oxygen bonds as well as carbon-carbon double bond remain intact under the reaction conditions. Epoxides also react with thiourea or ammonium thiocyanate in the presence of Mg(HSO 4)2 to afford the corresponding thiiranes in good to excellent yields.
- Salehi, Peyman,Khodaei, Mohammad Mahdi,Zolfigol, Mohammad Ali,Keyvan, Afsaneh
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p. 3041 - 3048
(2007/10/03)
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- Synthesis and antimicrobial activity of N,N-disubstituted 3-allyloxy-1-amino-2-propanethiols
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3-Allyloxy-1,2-epithiopropane was synthesized; its treatment with amines yielded N,N-disubstituted 3-allyloxy-1-amino-2-propanethiols, which were tested for antimicrobial activity.
- Allakhverdiev,Askerov
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p. 1280 - 1283
(2007/10/03)
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- Micellar media for the efficient ring opening of epoxides with CN-, N3-, NO3-, NO2-, SCN-, Cl- and Br- catalyzed with Ce(OTf)4
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Micellar media are introduced for the efficient ring opening of epoxides with sodium salts of nucleophiles such as CN, N3-, NO3-, NO2, SCN, Br and Cl-, catalyzed with Ce(OTf)4. This method is an efficient procedure for the synthesis of different β-substituted alcohols under mild reaction conditions. The reaction with SCN- is an easy procedure for the high yielding preparation of epoxy sulfides.
- Iranpoor, Nasser,Firouzabadi, Habib,Shekarize, Marzieh
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p. 724 - 727
(2007/10/03)
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- Polyvinylpyrrolidone/thionyl chloride as a new polymeric reagent for facile conversion of epoxides to β-chlorohydrins
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Epoxides undergo rapid ring opening with cross-linked polyvinylpyrrolidone/thionyl chloride complex, under mild reaction condition to afford chlorohydrins in high yields.
- Tamami, Bahman,Ghazi, Iraj,Mahdavi, Hossein
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p. 3725 - 3731
(2007/10/03)
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- Iron(III) trifluoroacetate as an efficient catalyst for solvolytic and nonsolvolytic nucleophilic ring opening of epoxides
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Iron(III) trifluoroacetate was used as an efficient and nonhygroscopic catalyst for the alcoholysis, hydrolysis, and acetolysis of epoxides. The addition of chloride, bromide, iodide, and nitrate ions to epoxides to produce the corresponding 2-halo and 2-nitratoalkanols and also the conversion of epoxides to acetonides and thiiranes were also performed efficiently in the presence of this catalyst.
- Iranpoor, Nasser,Adibi, Hadi
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p. 675 - 680
(2007/10/03)
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- Methyltriphenylphosphonium tetrahydroborate (MePh3PBH4). A stable, selective and versatile reducing agent
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Methyltriphenylphosphonium tetrahydroborate as a stable quaternary phosphonium borohydride is introduced. This compound is able to reduce aldehydes, ketones, acyl chlorides, and azides efficiently in CH2Cl2. α,β-Unsaturated carbonyl compounds are reduced selectively via 1,2-reduction. The effect of Lewis acids upon the mode and the rate of the reaction of epoxides and acetophenone are also described. This reagent is also able to bring about reductions effectively in the absence of solvent.
- Firouzabadi, Habib,Adibi, Mina
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p. 125 - 147
(2007/10/03)
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- Highly regio- and stereoselective synthesis of β-halohydrins from epoxides catalyzed with ceric ammonium nitrate
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Ce(IV) as ceric ammonium nitrate can effectively catalyze ring opening of epoxides with halides under very mild conditions and easy procedure to give the corresponding β-chloro- and β-bromohydrins in excellent yields. The reactions occur with both substituted and unsubstituted quaternary ammonium halides and with high regio- and stereoselectivity. The reaction of optically active styrene oxide with chloride ion was found to be highly stereospecific and afforded the corresponding β-halohydrin in 96% ee.
- Iranpoor,Kazemi,Salehi
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p. 1247 - 1258
(2007/10/03)
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- FeCl3·6H2O supported on SiO2 catalysed ring opening of epoxides with alcohols, acetic acid, water, chloride, bromide and nitrate ions
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FeCl3·6H2O absorbed on chromatographic silica gel can act as an efficient catalyst for alcoholysis, hydrolysis and acetolysis of epoxides. Methanolysis of (R)-styrene oxide proceeds with high stereospecificity and in excellent yield. This catalyst can also convert epoxides to their corresponding β-halohydrins and β-nitrato alcohols in the presence of chloride, bromide and nitrate ions respectively.
- Iranpoor, Nasser,Tarrian, Tahere,Movahedi, Zarangiz
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p. 1473 - 1476
(2007/10/03)
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- Reaction between 8-chlorotheophylline and epoxides. A simple preparation of oxazolido[2,3-f]purines
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The reaction of epoxides with 8-chlorotheophylline (1) produced the corresponding oxazolido[2,3-f]purines via nucleophilic addition and intramolecular nucleophilic substitution.
- Jin,Nishikubo
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p. 6307 - 6308
(2007/10/02)
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- HIGHLY REGIOSELECTIVE RING OPENING OF EPOXIDES WITH ALCOHOLS CATALYZED BY ORGANOTIN PHOSPHATE CONDENSATES
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Organotin phosphate condensates proved to catalyze the ring opening reaction of epoxides with alcohols in a highly regioselective manner.
- Otera, Junzo,Yoshinaga, Yukari,Hirakawa, Kazuhisa,Nakata, Tetsuya
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p. 3219 - 3222
(2007/10/02)
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- REACTIONS OF 1-CHLORO-2,3-EPOXYPROPANE WITH ALCOHOLS IN THE PRESENCE OF STANNIC CHLORIDE. II. DISTRIBUTION OF THE ADDITION PRODUCTS AND THE RELATIVE ACTIVITY OF THE ALCOHOLS
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In the distribution of the products from the reaction of 1-chloro-2,3-epoxypropane with alcohols in the presence of stannic chloride the determining factor is their capacity for complex formation with stannic chloride.This is confirmed by a correlation between the independently determined relative reaction constants and the constants for exchange of the alcohols and the complexes with stannic chloride.
- Drugov, M. V.,Barantsevich, E. N.,Smirnov P. A.
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p. 1052 - 1056
(2007/10/02)
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- EFFICIENT CATALYSIS OF HETEROPOLY ACID FOR ALCOHOLYSIS OF EPOXIDE
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Heteropoly acid (HPA) was found to catalyze the alcoholysis of epoxide more efficiently than the conventional acid catalysts such as sulfuric acid, perchloric acid and p-toluenesulfonic acid, at 45 deg C in the homogeneous liquid phase.The reason for the high catalytic activity of HPA is also discussed.
- Izumi, Yusuke,Hayashi, Kyoji
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p. 787 - 790
(2007/10/02)
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