- A facile approach to bis(Isoxazoles), promising ligands of the ampa receptor
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A convenient synthetic approach to novel functionalized bis(isoxazoles), the promising bivalent ligands of the AMPA receptor, was elaborated. It was based on the heterocyclization reactions of readily available electrophilic alkenes with the tetranitromethane-triethylamine complex. The structural diversity of the synthesized compounds was demonstrated. In the electrophysi-ological experiments using the patch clamp technique on Purkinje neurons, the compound 1,4-phenylenedi(methylene)bis(5-aminoisoxazole-3-carboxylate) was shown to be highly potent positive modulator of the AMPA receptor, potentiating kainate-induced currents up to 70% at 10?11 M.
- Averina, Elena B.,Grigoriev, Vladimir V.,Grishin, Yuri K.,Karlov, Dmitry S.,Kuznetsova, Tamara S.,Palyulin, Vladimir A.,Radchenko, Eugene V.,Rybakov, Victor B.,Sadovnikov, Kirill S.,Sedenkova, Kseniya N.,Vasilenko, Dmitry A.,Zamoyski, Vladimir L.
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- Multifunctional monomers based on vinyl sulfonates and vinyl sulfonamides for crosslinking thiol-Michael polymerizations: Monomer reactivity and mechanical behavior
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Multifunctional vinyl sulfonates and vinyl sulfonamides were conveniently synthesized and assessed in thiol-Michael crosslinking polymerizations. The monomer reactivities, mechanical behavior and hydrolytic properties were analyzed and compared with those of analogous thiol-acrylate polymerizations. Materials with a broad range of mechanical properties and diverse hydrolytic stabilities were obtained.
- Sinha, Jasmine,Podgórski, Maciej,Huang, Sijia,Bowman, Christopher N.
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supporting information
p. 3034 - 3037
(2018/03/28)
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- Chemoselective Transesterification of Acrylate Derivatives for Functionalized Monomer Synthesis Using a Hard Zinc Alkoxide Generation Strategy
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A new practical method for the synthesis of functionalized acrylate derivatives with the view to prepare functional polymers was explored. Hard zinc alkoxide generation enabled the highly chemoselective transesterification of acrylate derivatives over the undesired conjugate addition, which caused polymerization. The combined use of the catalytic zinc cluster Zn4(OCOCF3)6O and 4-(dimethylamino)pyridine delivered various functionalized acrylate derivatives through the transesterification of commercially available methyl acrylate derivatives with functionalized alcohols under mild conditions.
- Nakatake, Daiki,Yazaki, Ryo,Ohshima, Takashi
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supporting information
p. 3696 - 3699
(2016/08/20)
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- Synthesis and activity of novel homodimers of Morita–Baylis–Hillman adducts against Leishmania donovani: A twin drug approach
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It is reported here the synthesis of novel Homodimers 12–19 of Morita–Baylis–Hillman adducts (MBHA) from one-pot Morita–Baylis–Hillman Reaction (MBHR) between aromatic aldehydes as eletrophiles and ethylene glycol diacrylate as Michael acceptor (35–94% yields) using cheap and green conditions. The bioactivities were evaluated against promastigote form of Leishmania donovani. All homodimers showed to be more potent than corresponding monomers. It is worth highlighting that the halogenated homodimers 17 and 18 (0.50?μM) is almost 400 times more active than the corresponding monomer 10 and 1.24 times more potent than the second-line drug amphotericin B (0.62?μM). Moreover, the selectivity index to 18 is very high (SIrb?>?400) far better than amphotericin B (SIrb?=?18.73). This is the first report of twin drugs strategy applied on Morita–Baylis–Hillman adducts.
- da Silva, Wagner A.V.,Rodrigues, Daniele C.,de Oliveira, Ramon G.,Mendes, Rhuan K.S.,Olegário, Tayná R.,Rocha, Juliana C.,Keesen, Tatjana S.L.,Lima-Junior, Claudio G.,Vasconcellos, Mário L.A.A.
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supporting information
p. 4523 - 4526
(2016/08/24)
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- Method for catalytically synthesizing diethylene glycol di(methyl) acrylate by calcium glyceroxide
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The invention discloses a method for catalytically synthesizing diethylene glycol di(methyl) acrylate by calcium glyceroxide, and belongs to the field of fine chemical engineering. (Methyl) alkyl acrylate and diethylene glycol are used as raw materials; a reaction-rectification coupling process is adopted; a copper-wire-net-filled modified rectification column is used; the catalyst calcium glyceroxide is added; enough product purity and yield can be obtained after a simple aftertreatment process. The method overcomes multiple disadvantages of an existing transesterification catalyst, and is high in yield and simple in post-processing. Compared with a conventional transesterification method, the method provided by the invention can improve the total yield and the processing capacity; energy needed for separation is supplied by utilizing reaction heat, so that the energy consumption is decreased, and an investment is reduced. The method provided by the invention is simple and short in process flow; the raw materials are easily obtained; equipment is simple; reaction conditions are easy to control. The method is mild in the reaction conditions and simple in purification and refining processes; a product is stable, is easy to separate, and is not liable to generate a polymerization phenomenon.
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Paragraph 0041; 0042
(2017/01/02)
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- Method for synthesizing (methyl) acrylate glyceride through catalysis of calcium glyceroxide
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The invention discloses a method for synthesizing (methyl) acrylate glyceride through catalysis of calcium glyceroxide and belongs to the field of fine chemical engineering. The method comprises the steps that a reaction-rectification technology is adopted, a refit rectification column filled with copper wire gauze is used, and alkyl (meth) acrylate, glycerol, a polymerization inhibitor and a catalyst are added; under the string condition, air is introduced, and heating is carried out until a reaction solution flows back, wherein the temperature ranges from 60 DEG C to 140 DEG C; after the reaction is finished, a reaction solution is cooled to 50 DEG C, active carbon is added, stirring is continuously carried out for 0.5-1 h with the temperature maintained, the reaction solution is subjected to pressure reduction suction filtration after the reaction is finished, filter liquor is subjected to pressure reduction rotary steaming to remove the excessive raw material ester, and the (methyl) acrylate glyceride reactive diluent product is obtained. The method overcomes the defects of an existing ester exchange catalyst, and is high in yield, simple in aftertreatment and easy to implement.
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Paragraph 0041; 0042
(2017/09/14)
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- Low molecular weight PEI-based polycationic gene vectors via Michael addition polymerization with improved serum-tolerance
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A series of polycationic gene delivery vectors were synthesized via Michael addition from low molecular weight PEI and linking compounds with various heteroatom compositions. Agarose gel electrophoresis results reveal that these polymers can well condense plasmid DNA and can protect DNA from degradation by nuclease. The formed polyplexes, which are stable toward serum, have uniform spherical nanoparticles with appropriate sizes around 200-350 nm and zeta-potentials about +40 mV. In vitro experiments show that these polymers have lower cytotoxicity and higher transfection efficiency than 25 KDa PEI. Furthermore, the title materials exhibit excellent serum tolerance. With the present of 10% serum, up to 19 times higher transfection efficiency than PEI was obtained, and no obvious decrease of TE was observed even the serum concentration was raised to >40%. Flow cytometry and confocal microscopy studies also demonstrate the good serum tolerance of the materials.
- Xun, Miao-Miao,Xiao, Ya-Ping,Zhang, Ji,Liu, Yan-Hong,Peng, Qi,Guo, Qian,Wu, Wan-Xia,Xu, Yong,Yu, Xiao-Qi
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- FLEXIBLE TO RIGID NANOPOROUS POLYURETHANE-ACRYLATE (PUAC) TYPE MATERIALS FOR STRUCTURAL AND THERMAL INSULATION APPLICATIONS
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Novel urethane-acrylate (UAC) Star monomers and polyurethane-acrylate (PUAC) aerogel polymers derived therefrom are described herein, along with other novel, related monomers and polymers. Also described herein are processes for preparing the UAC Star monomers, the PUAC aerogel polymers, and the other related monomers and polymers. The PUAC and related polymers herein are useful in various applications including in structural and thermal insulation.
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- A unique aliphatic tertiary amine chromophore: Fluorescence, polymer structure, and application in cell imaging
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Although photoluminescence of tertiary aliphatic amines has been extensively studied, the usage of this fundamental chromophore as a fluorescent probe for various applications has unfortunately not been realized because their uncommon fluorescence is easily quenched, and strong fluorescence has been observed only in vapor phase. The objective of this study is how to retain the strong fluorescence of tertiary amines in polymers. Tertiary amines as branching units of the hyperbranched poly(amine-ester) (HypET) display relatively strong fluorescence (Φ = 0.11-0.43). The linear polymers with tertiary amines in the backbone or as the side group are only very weakly fluorescent. The tertiary amine of HypET is easily oxidized under ambient conditions, and red-shifting of fluorescence for the oxidized products has been observed. The galactopyranose-modified HypET exhibits low cytotoxicity and bright cell imaging. Thus, this study opens a new route of synthesizing fluorescent materials for cell imaging, biosensing, and drug delivery.
- Sun, Miao,Hong, Chun-Yan,Pan, Cai-Yuan
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supporting information
p. 20581 - 20584
(2013/02/22)
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- Hydroxy functional acrylate and methacrylate monomers prepared via lipase-catalyzed transacylation reactions
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Candida antarctica lipase B (CAL-B, Novozyme 435) catalyzes the transacylation of methyl acrylate and methyl methacrylate with diols and triols in 2-methyl-2-butanol at 50 °C. Under the experimental conditions, up to 70 mol% of the acyl donor methyl acrylate was converted. Methyl methacrylate is the less efficient acyl donor (up to 60 mol%) due to the higher sterical hindrance in the enzymatic transacylation. Under the reaction conditions high yields of the mono-acylated products are obtained, which contain minor amounts of bis(meth)acrylates. In addition it was observed that Novozyme 435 catalyzes regioselectively the acylation of the primary hydroxyl groups. In comparison with the chemical catalyzed route no selectivity was observed for unsubstituted diols. For substituted diols more mono-acylated product was formed in the lipase-catalyzed reaction than in the chemical catalyzed reaction.
- Popescu, Dragos,Hoogenboom, Richard,Keul, Helmut,Moeller, Martin
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experimental part
p. 80 - 89
(2010/08/20)
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- A process for the production of hydroxyalkyl (meth)acrylates
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The present invention relates to a process for producing high purity hydroxyalkyl (meth)acrylates. Specifically, the present invention relates to an improved process which can commercially and advantageously yield high purity hydroxyalkyl (meth)acrylates from (meth)acrylic acid and alkylene oxides.
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Page/Page column 3-4
(2008/12/07)
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- COMPOSITION FOR POLYELECTROLYTES, POLYELECTROLYTES, ELECTRICAL DOUBLE LAYER CAPACITORS AND NONAQUEOUS ELECTROLYTE SECONDARY CELLS
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A polymer electrolyte-forming composition containing (A) a quaternary ammonium salt of general formula (1) below and (B) an ionic liquid can be converted into a polymer without compromising the excellent properties of the ionic liquid, thus enabling an electrolyte having an excellent safety and electrical conductivity and also a broad potential window to be obtained. In formula (1), R1 to R3 are each independently an alkyl group of 1 to 5 carbons or a substituent having a reactive unsaturated bond and any two from among R1 to R3 may together form a ring, and R4 is methyl, ethyl or a substituent having a reactive unsaturated bond, with the proviso that at least one of R1 to R4 is a substituent having a reactive unsaturated bond. X is a monovalent anion, the letter m is an integer from 1 to 8, and the letter n is an integer from 1 to 4.
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- Process for the alkoxylation of organic compounds in the presence of novel framework materials
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The present invention relates to a process for the alkoxylation of organic compounds comprising the reaction of at least one organic compound with at least onealkoxylating agent in the presence of a catalyst system, wherein a polyetheralcohol is obtained. The catalyst system comprises a metallo organic framework mate-rial comprising pores and at least one metal ion and at least one at least bidentate organic compound, which is coordinately bounded to said metal ion. Furthermore it relates to polyurethanes or polyurethane foams, which are obtainable by using a prepared polyether alcohol as a starting material.
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- Production process for hydroxyalkyl (meth) acrylate
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There is disclosed a novel production process for a hydroxyalkyl (meth)acrylate in which: the diffusion of harmful substances due to disposal of catalysts can be reduced; and also the amount of the catalyst as used can be greatly saved in the entire production process. This production process comprises the step of carrying out a reaction between (meth)acrylic acid and an alkylene oxide in the presence of a catalyst in order to produce the hydroxyalkyl (meth)acrylate; with the production process being characterized by further comprising the step of recovering the catalyst as has been used for the reaction.
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- METHOD FOR THE PRODUCTION OF HYDROXYALKYL CARBONIC ACID ESTERS
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The invention relates to a heterogeneously catalyzed method for producing hydroxyalkyl carbonic acid esters from carbonic acids and alkylene oxides and the use thereof.
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Page/Page column 19
(2008/06/13)
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- Process for the preparation of hydroxyalkyl(meth)acrylate
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The present invention provides: a high-quality hydroxyalkyl (meth)acrylate of which the alkylene glycol di(meth)acrylate content and the acid component content are both low; and its novel production process. The hydroxyalkyl (meth)acrylate, which has a content, in terms of an alkylene glycol di(meth)acrylate as an impurity, of not more than 0.1 weight % and an acid component content of not more than 0.1 weight %, is obtained by a process comprising the step of carrying out a batch reaction between (meth)acrylic acid and an alkylene oxide in the presence of a catalyst in order to produce the hydroxyalkyl (meth)acrylate; with the process making an adjustment as to charging of both raw materials in such a manner that, for, of a time as needed for supplying both raw materials, a supplying time of not less than 40 % of a total supplying time when the raw materials as supplied have a temperature of not lower than 40 °C, the molar ratio of the integrated amount of the alkylene oxide to the integrated amount of the (meth)acrylic acid that have been added to a reactor by then can be more than 1.0.
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- Process for the conversion of aldehydes to esters
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A process for the conversion of aldehydes to esters, specifically acrolein or methacrolein to methyl acrylate or methyl methacrylate, respectively. Essentially in the absence of water, an aldehyde is contacted with an oxidizing agent to form an intermediate and then the intermediate is contacted with a diol or an alcohol to form an ester or diester. Preferably, the oxidizing agent is also a chlorinating agent. Specifically, acrolein or methacrolein is contacted with an oxidizing/chlorinating agent, such as t-butyl hypochlorite, and the chlorinated compound is contacted with an alcohol, such as methanol, to form methyl acrylate or methyl methacrylate, respectively. Generally, the order of addition is for the oxidizing agent to be added to the aldehyde, specifically for t-butyl hypochlorite to be added to acrolein or methacrolein, and for the diol or alcohol to be added to the intermediate, specifically for the methanol to be added to the reaction product of acrolein or methacrolein and t-butyl hypochlorite. The process of the present invention can be carried out in the absence or in the presence of solvent. Generally, better methyl acrylate or methyl methacrylate yields are obtained at lower reaction temperatures.
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Page/Page column 3-4
(2010/01/31)
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- Multiple Cycloadditive macrocyclization: An Efficient Method for Crown Ether-Type Cyclophanes, Bis-Calix[4]arenes and Silamacrocycles
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Macrocycles constitute a broad spectrum of compounds, which play a significant role in host-guest supramolecular chemistry. We have rationally designed an efficient novel synthetic method to synthesize different types of artificial receptive macrocycles containing isoxazoline or isoxazole ring systems. This method involves multiple (double, triple or quadrupole) cycloadditions between bifunctional dipoles and bifunctional dipolarophiles. We have presented our synthetic results to show the ease with which this one-pot synthetic method can be extended to synthesize different types of macrocycles such as cyclophanes, bis-calix[4]arenes and silamacrocycles. Hence, with appropriate combination of bifunctional dipoles and bifunctional dipolarophiles, the ring size of macrocycles could be controlled. This multiple cycloadditive macrocyclization will be a useful arsenal for the synthesis of various macrocycles.
- Kim, Byeang Hyean,Jeong, Eun Jeong,Hwang, Gil Tae,Venkatesan, Natarajan
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p. 2191 - 2202
(2007/10/03)
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- Liquid oligomers containing acrylate unsaturation
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The liquid oligomeric compositions of this invention are made by the Michael addition reaction of acetoacetate functional donor compounds with multifunctional acrylate receptor compounds where the equivalent ratios of multifunctional acrylate to acetoacetate vary from >/=1:1 to >/=13.2:1 depending on the functionality of both multifunctional acrylate and acetoacetate. Unuseable gelled or solid oligomer products occur below the claimed ranges. The liquid oligomers of this invention are further crosslinked to make coatings, laminates and adhesives.
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