5669-19-2Relevant academic research and scientific papers
A convenient synthesis of α-benzylacrylic acid
Issa,Andrews,Iskander,Reiss
, p. 1489 - 1494 (1995)
A convenient and reliable two-stage synthesis of α-benzyl-acrylic acid from diethyl benzylmalonate in 72% yield and good purity is reported. The synthesis compares favourably with the other procedures tested.
Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates
Ji, Xiaolei,Shen, Chaoren,Tian, Xinxin,Dong, Kaiwu
supporting information, p. 8645 - 8649 (2021/10/25)
A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.
Macrolactam Synthesis via Ring-Closing Alkene-Alkene Cross-Coupling Reactions
Goh, Jeffrey,Loh, Teck-Peng,Maraswami, Manikantha
supporting information, p. 9724 - 9728 (2020/12/21)
Reported herein is a practical method for macrolactam synthesis via a Rh(III)-catalyzed ring closing alkene-alkene cross-coupling reaction. The reaction proceeded via a Rh-catalyzed alkenyl sp2 C-H activation process, which allows access to macrocyclic molecules of different ring sizes. Macrolactams containing a conjugated diene framework could be easily prepared in high chemoselectivities and Z,E stereoselectivities.
Highly Selective Sub-Nanomolar Cathepsin S Inhibitors by Merging Fragment Binders with Nitrile Inhibitors
Schade, Markus,Merla, Beatrix,Lesch, Bernhard,Wagener, Markus,Timmermanns, Simone,Pletinckx, Katrien,Hertrampf, Torsten
supporting information, p. 11801 - 11808 (2020/11/26)
Pharmacological inhibition of cathepsin S (CatS) allows for a specific modulation of the adaptive immune system and many major diseases. Here, we used NMR fragment screening and crystal structure-aided merging to synthesize novel, highly selective CatS inhibitors with picomolar enzymatic Ki values and nanomolar functional activity in human Raji cells. Noncovalent fragment hits revealed binding hotspots, while the covalent inhibitor structure-activity relationship enabled efficient potency optimization.
A by 3 - phenyl -1 - methylacetylene preparation quickly disintegrating process method (by machine translation)
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Paragraph 0014-0016, (2019/07/10)
A by 3 - phenyl - 1 - propyne preparation quickly disintegrating process method, which belongs to the technical field of pharmaceutical intermediates. In the preparation quickly disintegrating in the process, intermediate benzyl acrylic acid yield and purity of the most important, this method first using 3 - phenyl - 1 - propyne as the raw material, in the palladium catalyst Pd2 (Dba)3 And the ligand dppp with ethyl carbonate under the catalysis of the reaction to the one-step synthesis of benzyl acrylic acid, its advantage lies in atmospheric pressure to complete the addition reaction, functional group tolerance is good, high efficiency, high purity, the production process is greatly simplified, and to obtain the target product preparation process of yield and purity than the traditional process much higher. The method has the advantages of greatly improve the productivity, reduce the cost, improve the safety, energy saving and the like, in accordance with the green reaction of modern chemical production requirement. (by machine translation)
Direct Access to Versatile Electrophiles via Catalytic Oxidative Cyanation of Alkenes
Gao, De-Wei,Vinogradova, Ekaterina V.,Nimmagadda, Sri Krishna,Medina, Jose M.,Xiao, Yiyang,Suciu, Radu M.,Cravatt, Benjamin F.,Engle, Keary M.
supporting information, p. 8069 - 8073 (2018/06/22)
Nucleophilic attack on carbon-based electrophiles is a central reactivity paradigm in chemistry and biology. The steric and electronic properties of the electrophile dictate its reactivity with different nucleophiles of interest, allowing the opportunity to fine-tune electrophiles for use as coupling partners in multistep organic synthesis or for covalent modification of proteins in drug discovery. Reactions that directly transform inexpensive chemical feedstocks into versatile carbon electrophiles would therefore be highly enabling. Herein, we report the catalytic, regioselective oxidative cyanation of conjugated and nonconjugated alkenes using a homogeneous copper catalyst and a bystanding N-F oxidant to furnish branched alkenyl nitriles that are difficult to prepare using existing methods. We show that the alkenyl nitrile products serve as electrophilic reaction partners for both organic synthesis and the chemical proteomic discovery of covalent protein ligands.
Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling
Wang, Kuai,DIng, Zhengtian,Zhou, Zhijun,Kong, Wangqing
supporting information, p. 12364 - 12368 (2018/10/05)
A Ni-catalyzed enantioselective reductive diarylation of activated alkenes by domino cyclizative/cross-coupling of two aryl bromides is developed. This reaction proceeds under very mild conditions and shows broad substrate scope, without requiring the use of preformed organometallic reagents. Moreover, this approach provides direct access to various bis-heterocycles bearing all-carbon quaternary centers in synthetically useful yields (up to 81%) with excellent enantioselectivity (>30 examples, 90-99% ee).
Compounding method for racecadotril intermediate
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Paragraph 0025; 0028; 0031, (2017/05/03)
The invention discloses a compounding method for a racecadotril intermediate. The compounding method comprises the following steps: causing ethyl phenylpropiolate, dimethylamine and trioxymethylene react with each other, treating with hydrochloric acid to obtain benzyl ethyl acrylate, and then hydrolyzing under an alkaline condition, thereby obtaining benzyl acrylic acid. According to the compounding method disclosed by the invention, benzyl chloride with higher toxicity is replaced by ethyl phenylpropiolate, the compounding route is shortened, the production efficiency is increased, and thus the compounding method is suitable for industrial production.
Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes
Song, Shengjin,Lu, Ping,Liu, Huan,Cai, Sai-Hu,Feng, Chao,Loh, Teck-Peng
supporting information, p. 2869 - 2872 (2017/06/13)
A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.
Preparation method of alpha, beta-unsaturated carboxylic acid compounds
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Paragraph 0054; 0055; 0056; 0057; 0058; 0059; 0125-0129, (2016/10/07)
The invention provides a preparation method of alpha, beta-unsaturated carboxylic acid compounds. The method is characterized in that compounds represented by formula (I) react with formic acid in the presence of a nickel-containing catalyst, a phosphine ligand and an organic solvent to obtain the alpha, beta-unsaturated carboxylic acid compounds represented by formula (II), wherein R1 and R2 are respectively independently selected from H, C1-C30 alkyl groups, C1-C30 substituted alkyl groups, C1-C30 alkenyl groups, C1-C30 substituted alkenyl groups, C6-C30 aryl groups and C6-C30 substituted aryl groups. Compared with the prior art, the method adopting formic acid as a carboxylation reagent has the advantages of low price, safety, stability, low toxicity, high yield, simple operation, good economy, avoiding of use of precious metal catalysts and toxic gas carbon monoxide, meeting of requirements of environmentally friendly compounds, wide function group compatibility, high conversion rate and industrial synthesis values.
