696-60-6Relevant academic research and scientific papers
Method for synthesizing hydroxybenzylamine
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Paragraph 0046-0052, (2020/02/27)
The invention discloses a method for synthesizing hydroxybenzylamine, and belongs to the technical field of organic synthesis. The principle of the method comprises that a demethylation reaction is carried out on methoxybenzylamine under the action of hydrobromic acid; the method is characterized in that methoxybenzylamine and hydrobromic acid are distilled in a reflux state to remove redundant water so as to increase the reaction temperature and increase the concentration of the hydrobromic acid in a reaction mixture, so that the demethylation effect of hydrobromic acid on methoxybenzylamineis enhanced, the reaction time is shortened, and the conversion rate is increased; when no bromomethane gas generation is observed, distillation is continued, excessive hydrobromic acid is recovered to further improve the reaction temperature and the conversion rate, meanwhile, the consumption of the raw material hydrobromic acid is reduced, and the treatment capacity of subsequent steps and the consumption of the raw material sodium hydroxide can also be reduced; therefore, the method has the advantages of simple technological process; the reaction time is short; the product is easy to purify; raw material consumption is low; the reaction yield is high.
Preparation of a magnetic mesoporous Fe3O4-Pd@TiO2 photocatalyst for the efficient selective reduction of aromatic cyanides
Zhao, Ziming,Long, Yu,Luo, Sha,Wu, Wei,Ma, Jiantai
, p. 6294 - 6302 (2019/04/25)
Herein, a hierarchical magnetic mesoporous microsphere was successfully prepared as a photocatalyst via a simple and reproducible route. Typically, Pd nanoparticles (NPs) were evenly dispersed on the surface of a magnetic Fe3O4 microsphere and then coated with a porous anatase-TiO2 shell to form Fe3O4-Pd@TiO2. The core-shell structure could efficiently suppress the conglomeration of Pd NPs during the calcination process at high temperatures as well as the shedding of Pd during the catalytic reaction process in the liquid phase. The as-prepared photocatalyst was characterized by TEM, XRD, XPS, VSM, and N2 adsorption-desorption. Fe3O4-Pd@TiO2 exhibits high photocatalytic activity for the selective reduction of aromatic cyanides to aromatic primary amines in an acidic aqueous solution. Moreover, this magnetic photocatalyst could be easily recovered from the reaction mixture by an external magnet and reused five times without significant reduction in its activity. The superior photocatalytic efficiency of the proposed photocatalyst may be attributed to its high charge separation efficiency and charge transfer rate, which are caused by the Schottky junction and large interface area. The results indicate that the strategy of coating the active noble metal sites with a mesoporous semiconductor shell has a significant potential for application in metal-semiconductor-based photocatalytic reactions.
Metagenomic discovery of a novel transaminase for valorization of monoaromatic compounds
Pawar, Sandip V.,Hallam, Steven J.,Yadav, Vikramaditya G.
, p. 22490 - 22497 (2018/06/29)
The profitability of next-generation biorefineries is acutely contingent on the discovery and utilization of biocatalysts that can valorize lignin. To this end, the metabolic catalogues of diverse microbiota have been mined previously using functional metagenomics in order to identify biocatalysts that can selectively degrade lignin into monoaromatic compounds. Herein, we have further improved the valorization factor of biorefining by deploying functional metagenomics toward the identification of a novel transaminase that can selectively functionalize lignin-derived monoaromatics to produce value-added feedstocks for pharmaceutical synthesis. We implemented a high-throughput colorimetric assay using o-xylylenediamine as the amino donor and successfully identified a transaminase that utilizes the canonical cofactor, pyridoxal 5′-phosphate, to aminate as many as 14 monoaromatic aldehydes and ketones. We subsequently identified the optimal conditions for enzyme activity towards the most favoured amino acceptor, benzaldehyde, including temperature, pH and choice of co-solvent. We also evaluated the specificity of the enzyme towards a variety of amino donors, as well as the optimal concentration of the most favoured amino donor. Significantly, the novel enzyme is markedly smaller than typical transaminases, and it is stably expressed in E. coli without any modifications to its amino acid sequence. Finally, we developed and implemented a computational methodology to assess the activity of the novel transaminase. The methodology is generalizable for assessing any transaminase and facilitates in silico screening of enzyme-substrate combinations in order to develop efficient biocatalytic routes to value-added amines. The computational pipeline is an ideal complement to metagenomics and opens new possibilities for biocatalyst discovery.
A metagenomics approach for new biocatalyst discovery: Application to transaminases and the synthesis of allylic amines
Baud, Damien,Jeffries, Jack W. E.,Moody, Thomas S.,Ward, John M.,Hailes, Helen C.
, p. 1134 - 1143 (2017/08/14)
Transaminase enzymes have significant potential for the sustainable synthesis of amines using mild aqueous reaction conditions. Here a metagenomics mining strategy has been used for new transaminase enzyme discovery. Starting from oral cavity microbiome samples, DNA sequencing and bioinformatics analyses were performed. Subsequent in silico mining of a library of contiguous reads built from the sequencing data identified 11 putative Class III transaminases which were cloned and overexpressed. Several screening protocols were used and three enzymes selected of interest due to activities towards substrates covering a wide structural diversity. Transamination of functionalized cinnamaldehydes was then investigated for the production of valuable amine building blocks.
MANUFACTURING METHOD OF AROMATIC COMPOUND AND FURAN DERIVATIVE HAVING METHYLAMINO GROUP
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Paragraph 0034; 0035, (2017/10/26)
PROBLEM TO BE SOLVED: To provide a method for manufacturing an aromatic compound or a furan derivative where only aldehyde group is converted to an aminomethyl group while maintaining a structure of aromatic or furan ring from an aromatic compound or a furan derivative having an aldehyde group, capable of being conducted in a water solvent containing no organic solvent and relatively low in by-product. SOLUTION: Amine or ammonia is added in water at first to convert to imine, then a reaction is conducted by using compressive hydrogen with a pressure of 0.1 MPa to 4 MPa in the presence of a metal carried solid catalyst carrying one or more kind of metal selected from rhodium, palladium and platinum or an alloy containing these metal elements. SELECTED DRAWING: Figure 2 COPYRIGHT: (C)2017,JPOandINPIT
Itopride intermediate preparation method
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Paragraph 0016, (2016/10/17)
The present invention relates to an itopride intermediate p-hydroxybenzylamine monohydrate preparation method, to be more specific, water is used as a solvent for reaction, p-hydroxybenzylamine can be obtained by one-step hydrogenation reduction of p-hydroxybenzaldehyde, alkalis, ammonia, under the effect of Raney nickel, the water is used for replacing an organic solvent as the solvent, the problem of safety of a traditional p-hydroxybenzylamine preparation process can be solved, and the itopride intermediate p-hydroxybenzylamine monohydrate preparation method is economized and environmentally-friendly and can meet the safe production requirements.
Reductive amination of furfural to furfurylamine using aqueous ammonia solution and molecular hydrogen: An environmentally friendly approach
Chatterjee, Maya,Ishizaka, Takayuki,Kawanami, Hajime
supporting information, p. 487 - 496 (2016/01/30)
A simple and highly efficient method was developed for the transformation of furfural (a biomass derived aldehyde) to furfurylamine by reductive amination using an aqueous solution of ammonia and molecular hydrogen as an amine source and a reducing agent, respectively. By choosing a suitable catalyst, such as Rh/Al2O3, and reaction conditions, a very high selectivity of furfurylamine (～92%) can be achieved within the reaction time of 2 h at 80 °C. A detailed analysis of the reaction system sheds some light on the reaction pathway and provides an understanding about each elementary step. The reaction was believed to proceed via an imine pathway although no such intermediate was detected because of the highly reactive nature. Optimization of different reaction parameters such as hydrogen pressure, temperature and substrate/ammonia mole ratio is shown to be critical to achieve high selectivity of furfurylamine. Time-dependent reaction profiles suggested that a Schiff base type intermediate was in the detectable range, which offers indirect evidence of the formation of imine. Competitive hydrogenation and amination of an aldehyde group were strongly dictated by the nature of the metal used. The studied protocol represents an environmentally benign process for amine synthesis, which can be effectively extended to the other aldehydes also. The studied catalyst could be recycled successfully without any significant loss of catalytic activity.
Selective catalytic transfer hydrogenation of nitriles to primary amines using Pd/C
Vilches-Herrera, Marcelo,Werkmeister, Svenja,Junge, Kathrin,Boerner, Armin,Beller, Matthias
, p. 629 - 632 (2014/03/21)
The catalytic transfer hydrogenation of (hetero)aryl nitriles using ammonium formate has been investigated in detail. In the presence of commercially available Pd/C, a straightforward and selective reduction is achieved without any additives under mild conditions.
N6-benzyladenosine derivatives as novel n-donor ligands of platinum(ii) dichlorido complexes
Starha, Pavel,Popa, Igor,Travnicek, Zdenek,Vanco, Jan
, p. 6990 - 7003 (2013/07/26)
The platinum(II) complexes trans-[PtCl2(Ln)2]·xSolv 1-13 (Solv = H2O or CH3OH), involving N6-benzyladenosine-based N-donor ligands, were synthesized; Ln stands for N6-(2-methoxybenzyl)adenosine (L1, involved in complex 1), N6-(4-methoxybenzyl) adenosine (L2, 2), N6-(2-chlorobenzyl)adenosine (L3, 3), N6-(4-chlorobenzyl)- adenosine (L4, 4), N6-(2-hydroxybenzyl)adenosine (L5, 5), N6-(3-hydroxybenzyl)- adenosine (L6, 6), N6-(2-hydroxy-3-methoxybenzyl) adenosine (L7, 7), N6-(4-fluorobenzyl) adenosine (L8, 8), N6-(4-methylbenzyl) adenosine (L9, 9), 2-chloro-N6-(3-hydroxybenzyl) adenosine (L10, 10), 2-chloro-N6-(4-hydroxybenzyl)adenosine (L11, 11), 2-chloro- N6-(2-hydroxy-3- methoxybenzyl)adenosine (L12, 12) and 2-chloro-N6-(2-hydroxy-5- methylbenzyl)adenosine (L13, 13). The compounds were characterized by elemental analysis, mass spectrometry, IR and multinuclear (1H-, 13C-, 195Pt- and 15N-) and two-dimensional NMR spectroscopy, which proved the N7-coordination mode of the appropriate N6-benzyladenosine derivative and trans-geometry of the title complexes. The complexes 1-13 were found to be non-toxic in vitro against two selected human cancer cell lines (HOS and MCF7; with IC50 > 50.0 μM). However, they were found (by ESI-MS study) to be able to interact with the physiological levels of the sulfur-containing biogenic biomolecule L-methionine by a relatively simple 1:1 exchange mechanism (one Ln molecule was replaced by one L-methionine molecule), thus forming a mixed-nitrogen/sulfur-ligand dichlorido-platinum(II) coordination species.
Studies on the synthesis, pungency and anti-biofouling performance of capsaicin analogues
Peng, Bixian,Wang, Junlian,Peng, Zhenghong,Zhou, Shengze,Wang, Fengqi,Ji, Yongliang,Ye, Zhangji,Zhou, Xiangfeng,Lin, Tong,Zhang, Xiaobin
body text, p. 435 - 442 (2012/10/07)
Ten capsaicin analogues were synthesized and their pungency degrees were determined through Scoville Organoleptic Test. The relationship between the structure and pungency degree of these capsaicin analogues was discussed. Then four of these capsaicin analogues with higher pungency degree were picked out and added to anti-biofouling paints as repellents to study their anti-biofouling performance by shallow sea buoyant raft hung-plate experimentation. The results showed that capsaicin and dihydrocapsaicin exhibited equally good anti-biofouling performance while nordihydrocapsaicin and N-vanillylnonanamide had poor anti-biofouling performance. Experimental results also showed that the paints with only 0.1% capsaicin or dihydrocapsaicin as repellent without any other biocides had also exhibited good anti-biofouling performance, which provided a new idea for developing novel, more environment-friendly and Cu 2O-free antifouling paints.
