627-45-2Relevant academic research and scientific papers
Microsomal oxidation of N,N-diethylformamide and its effect on P450- dependent monooxygenases in rat liver
Amato,Longo,Mazzaccaro,Gervasi
, p. 882 - 890 (1996)
N,N-Diethylformamide (DEF) is a hepatotoxic polar solvent in which metabolism has not been investigated. In this study we examined the following: (a) the oxidative metabolism of DEF using both liver microsomes from rats pretreated with selected P450 inducers and purified P450 enzyme (2B1, 2E1, 2C11); and (b) the effect of administration of DEF and its metabolite, the monoethylformamide (MEF), on induction and/or inhibition of the P450 isoforms in rats. DEF was deethylated by microsomal P450-dependent oxidation forming acetaldehyde and MEF according to Michaelis-Menten kinetic parameters. Microsomes from rats pretreated with acetone and pyrazole (selective P4502E1 inducers) or rats pretreated with dexamethasone and 200 mg/kg DEF were able to deethylate DEF in a biphasic manner, showing a low K(m) component with a V(max) of about 0.2 nmol/(min·mg of protein) and a K(m) between 70 μM and 250 μM. The low K(m) component was not present in control microsomes or in microsomes from rats treated with phenobarbital, β- naphthoflavone, or clofibrate, where linear kinetics were observed. The use of purified P4502E1 and 2C11 in a reconstituted system showed that 2E1, which oxidized DEF with a V(max) of 4.5 nmol/(min·nmol of P450) and a K(m) of 0.7 mM, can partially account for the low K(m) DEF deethylase, whereas 2C11, which oxidized DEF with a V(max) of 4.8 nmol/(min·nmol of P450) and a K(m) of 17 mM, might be the high K(m) deethylase. The purified 2B1 was barely able to deethylate DEF. A confirmation of the role of 2E1 in DEF metabolism was obtained by using various selective inhibitors of P450 isoforms and immunoprecipitation experiments with anti P4502E1 IgG. The low K(m) component of DEF deethylation in acetone-or pyrazole-induced microsomes was strongly inhibited (~90%) by diethyldithiocarbamate, 4-methylpyrazole, and anti-2E1 IgG, but in 200 mg/kg DEF-induced microsomes the inhibition was partial, suggesting that other P450(s) may be involved. Administration of DEF 200 mg/kg ip for 4 days induced hepatic microsomal P4502E1-dependent aniline hydroxylase, P4502B1/2-linked pentoxyresorufin O-depentylase, 16β- testosterone hydroxylase P4503A1/2-associated erythromycin N-demethylase, and 6β-testosterone hydroxylase. Alternatively, the same dose regimen of MEF induced only the aniline hydroxylase and depressed the 3A1/2-linked activities. Immunoblot experiments verified these data. These findings indicate that DEF, at low concentrations, is predominantly oxidized by P4502E1 and that this enzyme may be induced in rodents by repeated MEF or DEF treatment, thereby increasing their own metabolism and potentially their cytotoxicity through the formation of ethyl isocyanate.
Tris(pyrazolyl)borate Cobalt-Catalyzed Hydrogenation of C=O, C=C, and C=N Bonds: An Assistant Role of a Lewis Base
Lin, Yang,Zhu, De-Ping,Du, Yi-Ran,Zhang, Rui,Zhang, Suo-Jiang,Xu, Bao-Hua
supporting information, p. 2693 - 2698 (2019/04/25)
The combination of tris(pyrazolyl)borate cobalt complexes and Lewis base is developed as an efficient catalyst precursor in the homogeneous hydrogenation. A broad substrate scope including carbonyls, alkenes, enamines, and imines is reduced with 60 atm of H2 at 60 °C. Mechanistic studies support the hydrogenation operates through a frustrated Lewis pair (FLP)-like reduction process. These results highlight the development of novel non-noble metal catalytic processes, when combined with the diverse small molecule activation chemistry associated with FLPs.
Synthetic method of N-mono-substituted alkyl formamide
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Paragraph 0024; 0025; 0026; 0027-0043; 0064; 0065, (2019/10/01)
The embodiment of the invention discloses a synthetic method of N-mono-substituted alkyl formamide. The synthetic method comprises the steps of enabling primary amine compounds to react with carbon monoxide, distilling, and rectifying to obtain the N-mono-substituted alkyl formamide under the catalytic action of a sodium alkoxide-alcohol solution, wherein the molar ratio of the primary amine compounds to the sodium alkoxide-alcohol solution is 1 to (0.002 to 0.008); according to the synthetic method disclosed by the invention, through selecting specific materials, the N-mono-substituted alkylformamide can be synthesized through a one-step method under the action of a specific catalyst, and the synthetic method has the advantages that the process is simple, no by-product is produced, the source of raw materials are rich, the cost is low, the production efficiency can be improved effectively, and the production cost can be reduced; in addition, the yield and purity of synthetic productscan also be improved.
Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides
Claes, Laurens,Janssen, Michiel,De Vos, Dirk E.
, p. 4297 - 4306 (2019/08/26)
Amino acids obtained by fermentation or recovered from protein waste hydrolysates represent an excellent renewable resource for the production of bio-based chemicals. In an attempt to recycle both carbon and nitrogen, we report here on a chemocatalytic, metal-free approach for decarboxylation of amino acids, thereby providing a direct access to primary amines. In the presence of a carbonyl compound the amino acid is temporarily trapped into a Schiff base, from which the elimination of CO2 may proceed more easily. After evaluating different types of aldehydes and ketones on their activity at low catalyst loadings (≤5 mol%), isophorone was identified as powerful organocatalyst under mild conditions. After optimisation many amino acids with a neutral side chain were converted in 28–99 % yield in 2-propanol at 150 °C. When the reaction is performed in DMF, the amine is susceptible to N-formylation. This consecutive reaction is catalysed by the acidity of the amino acid reactant itself. In this way, many amino acids were efficiently transformed to the corresponding formamides in a one-pot catalytic system.
Method for preparing methallyl alcohol and amide simultaneously
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Paragraph 0030-0031, (2017/11/29)
A method for preparing methallyl alcohol and amide simultaneously is characterized in that methylallyl carboxylate taken as a raw material and an amine compound taken as an ammonolysis agent react under the action of a catalyst to produce methallyl alcohol and an amide compound. The methylallyl carboxylate and the amine compound taken as the ammonolysis agent are firstly adopted, and the methallyl alcohol and the amide compound are obtained under the action of the catalyst. The reaction process is a bulk reaction, no solvents are added, almost no wastewater or salt are produced, and byproduct methyl allyl ether is not produced; the defect that a large number of wastewater is produced through hydrolysis is overcome due to adoption of ammonolysis, the methallyl alcohol and the amide compound are coproduced directly by use of ammonoysis, coupling production is realized, and the cost is reduced.
Electronic-grade formamide compound preparation method
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Paragraph 0066; 0067; 0068; 0069; 0070; 0071; 0072, (2016/11/14)
The present invention discloses an electronic-grade formamide compound preparation method, which comprises that: the pure product of an organic amine compound and a pure product having purity of methyl formate enter a tube reactor, and a reaction is performed, wherein the organic amine compound is monomethylamine, mono ethylamine or diethylamine, and during the material adding, the organic amine compound excesses 2-5 wt%; after the reaction, cooling is performed by using a cooler, the cooled material enters a buffer tank, one part of the material discharged from the buffer tank returns to the tube reactor, the other part of the material discharged from the buffer tank enters a receiving tank and then is pumped into a coarse distillation tower, the tower kettle temperature is controlled at less than or equal to 130 DEG C, the tower top temperature is less than or equal to 64 DEG C, and the tower kettle liquid detection results show that the formamide compound content is more than or equal to 95 wt%, and the organic amine compound content is less than or equal to 5 wt%; extraction is performed from the tower bottom, the extracted material is pumped to a light removing tower, negative pressure distillation is performed, and the tower kettle liquid detection results show that the formamide compound content is more than or equal to 99.5 wt%, and the organic amine compound content is less than or equal to 0.5 wt%; and the material obtained from the tower bottom is pumped to a rectification tower, negative pressure distillation is performed, and N-methylformamide is extracted from the tower top. The product prepared through the process of the present invention has the low metal content, and the detection result shows that the product achieves the electronic grade.
Conversion of nitroalkanes into carboxylic acids via iodide catalysis in water
Marcé, Patricia,Lynch, James,Blacker, A. John,Williams, Jonathan M. J.
supporting information, p. 1013 - 1016 (2016/01/16)
We report a new method for the conversion of nitroalkanes into carboxylic acids that achieves this transformation under very mild conditions. Catalytic amounts of iodide in combination with a simple zinc catalyst are needed to give good conversions into the corresponding carboxylic acids.
Gold-Catalyzed Reductive Transformation of Nitro Compounds Using Formic Acid: Mild, Efficient, and Versatile
Yu, Lei,Zhang, Qi,Li, Shu-Shuang,Huang, Jun,Liu, Yong-Mei,He, He-Yong,Cao, Yong
, p. 3029 - 3035 (2015/09/28)
Developing new efficient catalytic systems to convert abundant and renewable feedstocks into valuable products in a compact, flexible, and target-specific manner is of high importance in modern synthetic chemistry. Here, we describe a versatile set of mild catalytic conditions utilizing a single gold-based solid catalyst that enables the direct and additive-free preparation of four distinct and important amine derivatives (amines, formamides, benzimidazoles, and dimethlyated amines) from readily available formic acid (FA) and nitro starting materials with high level of chemoselectivity. By controlling the stoichiometry of the employed FA, which has attracted considerable interest in the area of sustainable chemistry because of its potential as an entirely renewable hydrogen carrier and as a versatile C1 source, a facile atom- and step-efficient transformation of nitro compounds can be realized in a modular fashion. Renewable formic acid as a flexible feedstock: A versatile heterogeneous gold-based catalytic system has been developed for the controlled, flexible, and target-specific reductive transformation of nitro compounds using stoichiometric equivalents of formic acid as a key starting material under mild and convenient conditions. The overall operational simplicity, high chemoselectivity, functional-group tolerance, and reusability of the catalyst make this approach an attractive and reliable tool for organic and process chemists.
A green protocol for the N-formylation of amines using molybdate sulfuric acid as a reusable solid catalyst
Karami, Bahador,Farahi, Mahnaz,Pam, Fariba
, p. 6292 - 6296 (2015/02/19)
A novel and efficient method for the N-formylation of amines via the reaction of orthoformates and amines is developed. The reactions are mediated by a catalytic amount of molybdate sulfuric acid as a heterogeneous solid acid.
Synthesis of N-formylated β-lactams using nano-sulfated TiO 2 as catalyst under solvent-free conditions
Hosseini-Sarvari, Mona,Safary, Ensieh,Jarrahpour, Aliasghar,Heiran, Roghaye
, p. 980 - 987 (2013/02/22)
An easily accessible catalyst, nano-sulfated titania, efficiently catalyzes the N-formylation of β-lactams and all types of amines (primary, secondary, aromatic, and aliphatic) in solvent-free conditions at room temperature.
