14091-15-7Relevant articles and documents
Bi-enzymatic Conversion of Cinnamic Acids to 2-Arylethylamines
Weise, Nicholas J.,Thapa, Prasansa,Ahmed, Syed T.,Heath, Rachel S.,Parmeggiani, Fabio,Turner, Nicholas J.,Flitsch, Sabine L.
, p. 995 - 998 (2020/01/21)
The conversion of carboxylic acids, such as acrylic acids, to amines is a transformation that remains challenging in synthetic organic chemistry. Despite the ubiquity of similar moieties in natural metabolic pathways, biocatalytic routes seem to have been overlooked for this purpose. Herein we present the conception and optimisation of a two-enzyme system, allowing the synthesis of β-phenylethylamine derivatives from readily-available ring-substituted cinnamic acids. After characterisation of both parts of the reaction in a two-step approach, a set of conditions allowing the one-pot biotransformation was optimised. This combination of a reversible deaminating and irreversible decarboxylating enzyme, both specific for the amino acid intermediate in tandem, represents a general method by which new strategies for the conversion of carboxylic acids to amines could be designed.
Method for synthesizing 4-bromo-D-phenylalanine
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, (2020/03/14)
The invention discloses a method for synthesizing 4-bromo-D-phenylalanine. The method comprises the following steps: adding diethyl acetylaminomalonate, sodium ethoxide and ethanol into a reaction bottle, heating the reaction bottle to 80 DEG C, performing a heat insulation reaction for 2 h, cooling the reaction bottle to 35 DEG C, adding 4-bromobenzyl bromide, performing a heat insulation reaction for 5 h, cooling the reaction bottle to 25 DEG C, performing reduced pressure concentrating crystallization to obtain diethyl (acetylamino)[(4-bromophenyl)methyl]malonate, adding sodium hydroxide, heating the reaction bottle to 45 DEG C, performing a heat insulation reaction for 4 h, and cooling the reaction bottle to 20 DEG C to achieve crystallization in order to obtain (acetylamino)[(4-bromophenyl)methyl]malonic acid; and adding a 60% W/V hydrochloric acid solution, heating the reaction bottle to 85 DEG C, keeping the temperature for 2 h, ending the obtained reaction, and performing concentrating crystallization to obtain the 4-bromo-D-phenylalanine. Compared with traditional technologies, the method in the invention has the advantages of mild reaction temperature, safety in operation, obtaining of the highly pure product, cheap and easily-available raw materials, and very low cost.
Organocatalytic Enantioselective Addition of α-Aminoalkyl Radicals to Isoquinolines
Liu, Xiangyuan,Liu, Yang,Chai, Guobi,Qiao, Baokun,Zhao, Xiaowei,Jiang, Zhiyong
supporting information, p. 6298 - 6301 (2018/10/09)
With a dual organocatalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer and under the irradiation with visible light, an enantioselective Minisci-type addition of α-amino acid-derived redox-active esters (RAEs) to isoquinolines has been developed. A variety of prochiral α-aminoalkyl radicals generated from RAEs were successfully introduced on isoquinolines, providing a range of valuable α-isoquinoline-substituted chiral secondary amines in high yields with good to excellent enantioselectivities.
Enhanced reduction of C-N multiple bonds using sodium borohydride and an amorphous nickel catalyst
Liu, Shouxin,Yang, Yihua,Zhen, Xiaoli,Li, Junzhang,He, Huimin,Feng, Juan,Whiting, Andrew
experimental part, p. 663 - 670 (2012/01/15)
Amorphous nickel powder (Ni0) was utilised as a catalyst under mild, aqueous, basic conditions for enhancing the sodium borohydride-mediated reduction of C-N multiple bonds such as oximes, imines, hydrazones and nitriles to produce the corresponding amines in good to excellent yields.
Convenient method for reduction of C-N double bonds in oximes, imines, and hydrazones using sodium Borohydride-Raney ni system
Yang, Yihua,Liu, Shouxin,Li, Junzhang,Tian, Xia,Zhen, Xiaoli,Han, Jianrong
experimental part, p. 2540 - 2554 (2012/07/27)
(Chemical Equation Presented) A practical method has been developed for reduction of C-N double bond in oximes, imines, and hydrazones with sodium borohydride catalyzed by Raney Ni. The reactions were carried out in basic aqueous solution, and the desired products were obtained in moderate yields after a simple procedure. This method can be applied to synthesize simpler aliphatic or aromatic amines and its analogs. Copyright Taylor & Francis Group, LLC.
Solid phase reduction of oxazolones using BER-Ni2B-A simple synthesis of N-benzoylphenylalanines
Sikdar, Atul P.,Chetri, Ajoy B.,Das, Pranab J.
, p. 2878 - 2881 (2007/10/03)
Borohydride exchange resin (BER)-Ni2B is successfully used as a reagent for the solid phase reduction of the C-4 exocyclic double bond of oxazolones to give the N-benzoylphenylalanines and hence the corresponding amino acids.
