3470-99-3Relevant articles and documents
Fatty acid decarboxylation reaction kinetics and pathway of co-conversion with amino acid on supported iron oxide catalysts
Bian, Junjie,Wang, Yue,Zhang, Qi,Fang, Xudong,Feng, Lijuan,Li, Chunhu
, p. 47279 - 47287 (2017)
Fe2O3/Al-MCM-41 nanocomposite catalysts were designed and fabricated to upgrade microalgae hydrothermal liquefaction (HTL)-derived biocrude and its model compounds (palmitic acid and glutamic acid) in the absence of hydrogen. The Fe
Bio-based N-alkyl-2-pyrrolidones by Pd-catalyzed reductive N-alkylation and decarboxylation of glutamic acid
De Schouwer, Free,Adriaansen, Sander,Claes, Laurens,De Vos, Dirk E.
, p. 4919 - 4929 (2017/10/19)
Environmental regulations boost the search for new safer and less toxic bio-based solvents to replace controversial high-boiling solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide in the chemical industry. Recently, N-alkyl-2-pyrrolidones and 5-methyl-N-alkyl-2-pyrrolidones were proposed as attractive alternative solvents for many applications. Here, we report a bio-based two-step chemocatalytic system for the synthesis of a broad range of N-alkyl-2-pyrrolidones starting from glutamic acid and C3-C5 carbonyl compounds. In the first step N-mono-alkylated derivatives of glutamic acid were synthesized in high yields (>85%) by a mild and efficient Pd-catalyzed reductive N-alkylation. Subsequently, thermally induced lactamization to the corresponding N-alkylpyroglutamic acid followed by Pd-catalyzed decarboxylation at 250 °C under inert atmosphere resulted in N-alkyl-2-pyrrolidones. Hydrolytic degradation was partially counteracted by the neutralization of the N-alkylpyroglutamic acid substrate with a base, resulting in yields up to 82%. Finally, both reaction steps were successfully combined in a one-pot process using the same Pd/Al2O3 catalyst in different conditions of gas atmosphere and temperature.
Novel Pyrrolinium-based Ionic Liquids for Lithium Ion Batteries: Effect of the Cation on Physicochemical and Electrochemical Properties
Kim, Hyung-Tae,Kwon, Oh Min,Mun, Junyoung,Oh, Seung M.,Yim, Taeeun,Kim, Young Gyu
, p. 267 - 276 (2017/04/26)
Lithium ion batteries (LIBs) are one of the most promising energy conversion/storage systems, but the low thermal stability of the current electrolytes in LIBs should be improved to expand their potential applications. To enhance the safety properties of LIBs, novel pyrrolinium-based ionic liquids (ILs) were proposed as an alternative electrolyte to the current carbonate electrolyte, which have some task-specific functional groups, i.e., a planar C[dbnd]N double bond, a C-O ether linkage, and no unstable C-H bond, designed to improve their electrochemical performances as well as the physicochemical properties. As a result, the pyrrolinium-based ILs exhibited much improved physicochemical and electrochemical properties compared to those of the known ILs. Among the prepared ILs, N-allyl-2-methoxypyrrolinium bis(fluorosulfonyl)imide (A(OMe)Pyrl-FSI, 4) showed the high ionic conductivity (10.2 mS cm?1), the very good cycling performance (99.3% of retention ratio after 50 cycles) with a LiFePO4 electrode, and the much improved lithium ion transference number (0.19). IL 4 also had the remarkable rate capability at 5 C-rate with the retention ratio of 81.2% (124.8 mA h g?1), compared to the initial discharge capacity of 153.7 mA h g?1 at 0.1 C-rate. In addition, both their high thermal stability and non-flammability were also confirmed.
Trifluralin haptens, as well as preparation method and application thereof
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Paragraph 0012; 0030, (2017/08/30)
The invention discloses trifluralin haptens, as well as a preparation method and application thereof. The trifluralin hapten has a structural formula as shown in the specification. The six haptens are specific antibodies which have linker arms derived on amino sites, have active carboxyls, enable a body to generate high titer after being coupled with carrier protein and can be used for identifying common structures of trifluralin pesticide. The hapten compound is simple and convenient in synthesizing method, has relatively high purity, and can be applied to synthesis of antigen systems of animal immune, so that the blank in the technical field of trifluralin immunological detection method in China can be filled, and foundation is laid for further development of trifluralin immunological detection method.
Synthesis of biobased N-methylpyrrolidone by one-pot cyclization and methylation of γ-aminobutyric acid
Lammens, Tijs M.,Franssen, Maurice C. R.,Scott, Elinor L.,Sanders, Johan P. M.
scheme or table, p. 1430 - 1436 (2010/09/05)
N-Methylpyrrolidone (NMP) is an industrial solvent that is currently based on fossil resources. In order to prepare it in a biobased way, the possibility to synthesize NMP from γ-aminobutyric acid (GABA) was investigated, since GABA can be obtained from glutamic acid, an amino acid that is present in many plant proteins. Cyclization of GABA to 2-pyrrolidone and subsequent methylation of 2-pyrrolidone to NMP was achieved in a one-pot procedure, using methanol as the methylating agent and a halogen salt (i.e. ammonium bromide) as a catalyst. A selectivity above 90% was achieved, as well as a high conversion. Methylation of 2-pyrrolidone could also be done with dimethyl carbonate, but then the selectivity for NMP was less (67%).
Synthesis, conformational characteristics and anti-influenza virus A activity of some 2-adamantylsubstituted azacycles
Setaki, Despina,Tataridis, Dimitris,Stamatiou, George,Kolocouris, Antonios,Foscolos, George B.,Fytas, George,Kolocouris, Nicolas,Padalko, Elizaveta,Neyts, Johan,Clercq, Erik De
, p. 248 - 273 (2008/02/07)
The broad-spectrum antiviral activity of 2-(2-adamantyl)piperidines 11, 13a,b, and 15, 3-(2-adamantyl)pyrrolidines 27, 21a-g and 2-(2-adamantylmethyl)piperidines 30, 32a-c, and 35a-d was examined. Several compounds in the new series were potent against influenza A H3N2 virus. When 1-aminoethyl pharmacophore group of 2-rimantadine 4 (2-isomer of rimantadine) is included into a saturated nitrogen heterocycle, see compound 11, potency was retained. The diamine derivatives 21e-g and particularly 35a-c possessing three pharmocophoric groups, that is, the adamantyl and the two amine groups, exhibited high potency. The new compounds did not afford specific activity at non-toxic concentrations against any of the other viruses tested. According to NMR spectroscopy and molecular mechanics calculations it is striking that the parent structures 11 and 27 adopt a fixed trans conformation around C2{single bond}C2′ bond. In the parent amines, which proved to be active compounds, the distance between nitrogen and adamantyl pharmacophoric groups was different; N{single bond}C2′ distance is 3.7, 3.8 A for 27, 30 and 2.5 A for 11 suggesting that M2 receptor site can accommodate different in size and orientation lipophilic cages.
Practical synthesis of an orally active CCR5 antagonist, 7-{4-[2-(Butoxy)-ethoxy]phenyl}-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino] methyl}phenyl)-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide
Ikemoto, Tomomi,Ito, Tatsuya,Nishiguchi, Atsuko,Miura, Syotaro,Tomimatsu, Kiminori
, p. 168 - 173 (2012/12/24)
A practical method of synthesizing 7-{4-[2-(butoxy)ethoxy]-phenyl}-N-(4- {[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}-phenyl)-1-propyl-2, 3-dihydro-1H-1-benzazepine-4-carboxamide (8), an orally active CCR5 antagonist, has been developed. Methyl 7-bromo-1-propyl-2,3-dihydro-1H-1-benzazepine-4- caboxylate (14a) was synthesized in good yield by the esterification of 4-[(4-bromo-2-formylphenyl)(propyl)amino]butanoic acid (13) followed by an intramolecular Claisen type reaction with 28% sodium methoxide in dimethyl carbonate as a solvent in one pot. The Suzuki-Miyaura reaction of 14a and 1-bromo-4-(2-butoxyethoxy)benzene (10) followed by hydrolysis and amidation gave 8. A new inexpensive method without chromatographic purification was established.
Ammonium formate/palladium on carbon: A versatile system for catalytic hydrogen transfer reductions of carbon-carbon double bonds
Paryzek, Zdzislaw,Koenig, Hanna,Tabaczka, Bartlomiej
, p. 2023 - 2026 (2007/10/03)
Various carbon-carbon double bonds in olefins and α,β -unsaturated ketones were effectively reduced to the corresponding alkanes and saturated ketones, using ammonium formate as a hydrogen transfer agent in the presence of Pd/C as catalyst in refluxing methanol.
PROCESS FOR THE PREPARATION OF 2,3-DIHYDROAZEPINE COMPOUNDS
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, (2008/06/13)
As a process for preparing 2,3-dihydroazepine compounds at low cost in a simple and easy manner, there is provided a process for the preparation of compounds of the formula: or salts thereof, characterized in that compounds of the formula: or salts thereof are reacted with compounds of the formula: or salts thereof to give compounds of the formula: or salts thereof, which are then subjected to esterification and ring-closing reaction.
Novel 3-(2-adamantyl)pyrrolidines with potent activity against influenza A virus - Identification of aminoadamantane derivatives bearing two pharmacophoric amine groups
Stamatiou, George,Kolocouris, Antonios,Kolocouris, Nicolas,Fytas, George,Foscolos, George B,Neyts, Johan,De Clercq, Erik
, p. 2137 - 2142 (2007/10/03)
The 3-(2-adamantyl)pyrrolidines 8a-g, 14 were synthesized and evaluated for activity against influenza A virus. The parent N-H compound 14 was several times more active than amantadine against H2N2 and H3N2 influenza A virus. The combined use of NMR spectroscopy and computational chemistry showed that the conformation around the pyrrolidine-adamantyl carbon-carbon bond is trans and the pyrrolidine heterocycle has an envelope conformation with C-2 out of the plane of the other ring atoms. N-Dialkylaminoethyl substitution of compound 14 resulted in the potent diamine analogues 8e,f,g. Interestingly, their lactam amine precursors were also active. Compounds 8e,f,g are the first adamantane derivatives, bearing two amine groups, reported to be active against influenza A virus.
