4151-98-8Relevant academic research and scientific papers
Rational design 2-hydroxypropylphosphonium salts as cancer cell mitochondria-targeted vectors: Synthesis, structure, and biological properties
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.
, (2021/11/01)
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.
MBA-cross-linked poly(N-vinyl-2-pyrrolidone)/ferric chloride macromolecular coordination complex as a novel and recyclable Lewis acid catalyst: Synthesis, characterization, and performance toward for regioselective ring-opening alcoholysis of epoxides
Rahmatpour, Ali,Zamani, Maryam
, (2021/09/30)
A novel macromolecular-metal coordination complex, MBA-cross-linked PNVP/FeCl3 material was fabricated by immobilization of water intolerant ferric chloride onto the porous cross-linked poly(N-vinyl-2-pyrrolidone) carrier beads as a macromolecular ligand or carrier which was prepared by suspension free-radical copolymerization of N-vinyl-2-pyrrolidone (NVP) and N,N′-methylene bis-acrylamide (MBA) as a crosslinking agent in water. The obtained PNVP/FeCl3 was characterized by UV/vis and FT-IR spectroscopies, TGA, FE-SEM, EDX, and ICP techniques. This heterogenized version of ferric chloride is a convenient and safe alternative to highly water intolerant ferric chloride. The catalytic performance of (PNVP/FeCl3) as an efficient and recyclable polymeric Lewis acid catalyst was appropriately probed in the regio-and stereoselective nucleophilic ring opening of various epoxides with various alcohols in excellent yields with TOF up to 182.48 h?1 without generating any waste. The activity data indicate that this heterogeneous catalyst is very active and could be easily recovered, and reused at least six times without appreciable loss of activity indicating its stability under experimental conditions.
Readily Scalable Methodology for the Synthesis of Nonsymmetric Glyceryl Diethers by a Tandem Acid-/Base-Catalyzed Process
Leal-Duaso, Alejandro,Gracia-Barberán, Sara,Mayoral, José A.,Garciá, José I.,Pires, Elisabet
, p. 154 - 162 (2020/02/04)
A useful optimized synthetic methodology has been designed for the synthesis of nonsymmetric glyceryl diethers from epichlorohydrin. A tandem process combining a cheap, heterogeneous, and fully recoverable acid catalyst and alkaline hydroxide is used for the synthesis of a variety of glycerol-derived ethers bearing different alkyl substituents in 1 and 3 positions. Different heterogeneous acid catalysts have been tested for the reaction of epichlorohydrin with several alcohols, the best results being obtained with readily available recoverable and inexpensive montmorillonite-K10 and Nafion NR50. For the second reaction step, potassium hydroxide is used. In all the cases, good yields of the desired glyceryl diethers are obtained in smooth reaction conditions, always with total conversion of epichlorohydrin and without the need of intermediate purification. Scale-up of the tandem process has been carried out with good results.
Fiber-supported Fe(iii) complex catalyst in spinning basket reactor for cleaner ring-opening of epoxides with alcohols
Shi, Xian-Lei,Sun, Benyu,Hu, Qianqian,Chen, Yongju,Duan, Peigao
, p. 3573 - 3582 (2019/07/09)
Herein, a newly designed fiber-supported iron catalyst was successfully synthesized by rooting diamine ligands into the surface layer of commercially available polyacrylonitrile fiber and then utilizing the diamine groups to immobilize Fe(iii) ions for heterogeneous catalytic ring-opening reactions. The resulting materials were characterized and observed in detail by elemental analysis, mechanical properties, FTIR spectroscopy and morphology during both the preparation and the utilization processes. Moreover, the fiber catalyst was used in the spinning basket reactor-mediated ring-opening of various epoxides by a series of alcohols under mild reaction conditions, giving good to quantitative yields of the corresponding β-alkoxy alcohols. In addition, the fiber catalyst in the impellers of the agitation system was shown to be reusable multiple times without leaching of the Fe(iii) ions, and when stored on the shelf remained equally active for at least three months. Furthermore, the catalytic system was convenient and effective for scaling-up experiments and thereby has prospects in industrial applications.
An epoxide ring-opening reaction by using sol–gel-synthesized palladium supported on a strontium hydroxyl fluoride catalyst
Acham, Vaibhav R.,Dongare, Mohan K.,Kemnitz, Erhard,Umbarkar, Shubhangi B.
, p. 1237 - 1246 (2016/10/13)
Palladium supported on a strontium hydroxyl fluoride catalyst was synthesized by a one-pot fluorolytic sol–gel method. The prepared catalyst was characterized by various physicochemical techniques. The sol–gel method has led to the formation of a high surface area (57?m2g?1), mesoporous (pore diameter?=?13.0?nm) catalyst with uniform dispersion of Pd nanoparticles of size ～7?nm on the surface of strontium hydroxyl fluoride. The catalyst was used for epoxide alcoholysis, and 100% conversion was obtained with 96% selectivity for β-alkoxy alcohols under mild conditions. The catalyst could be recycled for up to three catalytic cycles without any appreciable decrease in conversion and selectivity, indicating the stability of the catalyst under the reaction conditions. Further, the mechanism of alcoholysis was proposed on the basis of the physicochemical characteristics of the catalyst and on the basis of the products formed during the catalytic reaction.
Enhanced metal loading in SBA-15-type catalysts facilitated by salt addition: Synthesis, characterization and catalytic epoxide alcoholysis activity of molybdenum incorporated porous silica
Budhi, Sridhar,Peeraphatdit, Chorthip,Pylypenko, Svitlana,Nguyen, Vy H.T.,Smith, Emily A.,Trewyn, Brian G.
, p. 469 - 476 (2014/03/21)
We report a novel method to increase the metal loading in SBA-15 silica matrix via direct synthesis. It was demonstrated through the synthesis and characterization of a series of molybdenum containing SBA-15 mesoporous silica catalysts prepared with and without diammonium hydrogen phosphate (DHP) as an additive. Catalysts prepared with DHP show a 2-3 times increase in incorporation of molybdenum in the silica matrix and pore size enlargement. The synthesized catalysts were characterized using nitrogen sorption, X-ray diffraction (XRD), Raman spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and inductively coupled plasma-optical emission spectroscopy (ICP-OES). The catalytic activity of catalysts prepared with DHP for alcoholysis of epoxides was superior than the catalyst prepared without DHP. Alcoholysis of epoxides was demonstrated for a range of alcohols and epoxides under ambient conditions in as little as 30 min with high selectivity.
Nucleophilic reactivity of ethers against terminal epoxides in the presence of BF3: A mechanistic study
Kose, Aytekin,Altundas, Ramazan,Secen, Hasan,Kara, Yunus
, p. 1325 - 1330 (2013/08/23)
In the presence of BF3, a series of symmetrical and unsymmetrical ethers reacted with epichlorohydrin and 2-[(benzyloxy)methyl] oxirane, two terminal epoxides, to afford 1-alkoxy-3-chloropropan-2-ol and 1-alkoxy-3-(benzyloxy)propan-2-ol. The cleavage of unsymmetrical ethers occurred via an SN2 or SN1 mechanism. Secondary epoxides did not give similar ring-opening products. Copyright
Efficient and regioselective ring-opening of epoxides with alcohols and sodium azide by using catalytic amounts of gacl3/polyvinylpyrrolidone
Pourali, Ali Reza,Ghayeni, Samaneh,Afghahi, Fatemeh
, p. 1741 - 1744 (2013/07/26)
A new polymeric catalyst was prepared by supporting GaCl3 on cross-linked polyvinylpyrrolidone (GaCl3/ PVP). This catalyst was employed for efficient and regioselective ring-opening reaction of epoxides by various alcohols under solvent-free conditions at room temperature. In our procedure, this heterogeneous catalyst was used at neutral and mild reaction conditions to afford high yields of β-alkoxy alcohols. Also, regioselective conversion of epoxides to β-azidohydrines was accomplished by sodium azide in MeOH in the presence of GaCl3/PVP at room temperature. GaCl3/PVP is a non-hygroscopic and recoverable catalyst and is easily separated from reaction mixture by a simple filtration and re-used repeatedly. Also, this catalyst has good handling and can be stored for long time without any reducing of its reactivity.
Mild and efficient ring opening of epoxides catalyzed by potassium dodecatungstocobaltate(III)
Tangestaninejad, Shahram,Moghadam, Majid,Mirkhani, Valiollah,Yadollahi, Bahram,Mirmohammadi, S. Mohammad R.
, p. 235 - 242 (2007/10/03)
Efficient ring opening of epoxides under mild conditions is reported. Potassium dodecatungstocobaltate(III) trihydrate was used as an efficient catalyst for the alcoholysis and acetolysis of epoxides. Conversion of epoxides to thiiranes was also performed efficiently in the presence of this catalyst. Springer-Verlag 2005.
Synthesis of 1-alkoxy-3-N-succinimido-2-propanols
Gasanov,Allakhverdiev
, p. 2026 - 2028 (2007/10/03)
Procedures for preparing 1-alkoxy-3-chloro-2-propanols, with their subsequent transformation to 1-alkoxy-N-succinimido-2-propanols, were developed.
