78573-45-2Relevant articles and documents
Green method for catalyzing deprotection of tetrahydropyrane ether into hydroxyl compound
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Paragraph 0026-0028, (2022/03/17)
The invention provides a green method for catalyzing deprotection of tetrahydropyrane ether into hydroxyl compound, and belongs to the field of green organic chemistry. According to the method, under neutral, open and room-temperature conditions, acetonitrile is used as a reaction solvent, FeBr2 or FeBr3 is used as a catalyst, H2O2 is used as an oxidizing agent, and a tetrahydropyrane ether derivative is converted into a hydroxyl compound within a short time. According to the invention, the catalyst FeBr2 and FeBr3, the oxidizing agent H2O2 and the solvent acetonitrile used in the method are cheap and easy to obtain, the reaction time is short, the condition is mild, the method has wide functional group compatibility, post-treatment is simple, operation is easy, and the method is a current green, environment-friendly and safe method for deprotecting the tetrahydropyrane ether derivative into the hydroxyl compound and has wide application prospects.
Access to Trisubstituted Fluoroalkenes by Ruthenium-Catalyzed Cross-Metathesis
Nouaille, Augustin,Pannecoucke, Xavier,Poisson, Thomas,Couve-Bonnaire, Samuel
supporting information, p. 2140 - 2147 (2021/03/06)
Although the olefin metathesis reaction is a well-known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross-Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post-functionalizable source of fluoroalkene, that we found as the methyl 2-fluoroacrylate. We reported herein the efficient ruthenium-catalyzed CM reaction of various terminal and internal alkenes with methyl 2-fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products. (Figure presented.).
Continuous-Flow Amide and Ester Reductions Using Neat Borane Dimethylsulfide Complex
?tv?s, Sándor B.,Kappe, C. Oliver
, p. 1800 - 1807 (2020/02/27)
Reductions of amides and esters are of critical importance in synthetic chemistry, and there are numerous protocols for executing these transformations employing traditional batch conditions. Notably, strategies based on flow chemistry, especially for amide reductions, are much less explored. Herein, a simple process was developed in which neat borane dimethylsulfide complex (BH3?DMS) was used to reduce various esters and amides under continuous-flow conditions. Taking advantage of the solvent-free nature of the commercially available borane reagent, high substrate concentrations were realized, allowing outstanding productivity and a significant reduction in E-factors. In addition, with carefully optimized short residence times, the corresponding alcohols and amines were obtained in high selectivity and high yields. The synthetic utility of the inexpensive and easily implemented flow protocol was further corroborated by multigram-scale syntheses of pharmaceutically relevant products. Owing to its beneficial features, including low solvent and reducing agent consumption, high selectivity, simplicity, and inherent scalability, the present process demonstrates fewer environmental concerns than most typical batch reductions using metal hydrides as reducing agents.
Carbene-Catalyzed α-Carbon Amination of Chloroaldehydes for Enantioselective Access to Dihydroquinoxaline Derivatives
Huang, Ruoyan,Chen, Xingkuan,Mou, Chengli,Luo, Guoyong,Li, Yongjia,Li, Xiangyang,Xue, Wei,Jin, Zhichao,Chi, Yonggui Robin
supporting information, p. 4340 - 4344 (2019/06/14)
An NHC-catalyzed α-carbon amination of chloroaldehydes was developed. Cyclohexadiene-1,2-diimines are used as amination reagents and four-atom synthons. Our reaction affords optically enriched dihydroquinoxalines that are core structures in natural products and synthetic bioactive molecules.
Chemical modification-mediated optimisation of bronchodilatory activity of mepenzolate, a muscarinic receptor antagonist with anti-inflammatory activity
Yamashita, Yasunobu,Tanaka, Ken-ichiro,Yamakawa,Asano,Kanda, Yuki,Takafuji,Kawahara, Masahiro,Takenaga, Mitsuko,Fukunishi, Yoshifumi,Mizushima
supporting information, p. 3339 - 3346 (2019/06/18)
The treatment for patients with chronic obstructive pulmonary disease (COPD) usually involves a combination of anti-inflammatory and bronchodilatory drugs. We recently found that mepenzolate bromide (1) and its derivative, 3-(2-hydroxy-2, 2-diphenylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide (5), have both anti-inflammatory and bronchodilatory activities. We chemically modified 5 with a view to obtain derivatives with both anti-inflammatory and longer-lasting bronchodilatory activities. Among the synthesized compounds, (R)-(–)-12 ((R)-3-(2-hydroxy-2,2-diphenylacetoxy)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octane bromide) showed the highest affinity in vitro for the human muscarinic M3 receptor (hM3R). Compared to 1 and 5, (R)-(–)-12 exhibited longer-lasting bronchodilatory activity and equivalent anti-inflammatory effect in mice. The long-term intratracheal administration of (R)-(–)-12 suppressed porcine pancreatic elastase-induced pulmonary emphysema in mice, whereas the same procedure with a long-acting muscarinic antagonist used clinically (tiotropium bromide) did not. These results suggest that (R)-(–)-12 might be therapeutically beneficial for use with COPD patients given the improved effects seen against both inflammatory pulmonary emphysema and airflow limitation in this animal model.
Synthesis of α-Substituted Primary Benzylamines through Copper-Catalyzed Cross-Dehydrogenative Coupling
Kramer, S?ren
, p. 65 - 69 (2019/01/04)
A copper-catalyzed route to α-substituted, primary benzylamines by C-H functionalization of alkylarenes is described. The method directly affords the amine hydrochloride salt. Catalyst loadings down to 0.1 mol % in combination with scalability, insensitivity to air and moisture, and no need for column chromatography makes the procedure highly practical. The facile synthesis of the racemate of a blockbuster drug highlights the relevance for the development of pharmaceuticals. Preliminary mechanistic data are also included.
Preparation method of 3-(3'-trifluoromethyl phenyl)propanol
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Paragraph 0044-0054, (2017/08/30)
The invention relates to a preparation method of 3-(3'-trifluoromethyl phenyl)propanol and solves the technical problems that preparation of 3-(3'-trifluoromethyl phenyl)propanol is complex to operate, a large number of reducing agents are consumed and the like in the prior art. The preparation method comprises the synthesis steps as follows: 3-(3-trifluoromethyl phenyl) propionic acid and organic amine react with halogenated formate in an organic solution to form mixed anhydride through activation, the mixed anhydride reacts with an alkali metal borohydride solution to produce the 3-(3'-trifluoromethyl phenyl)propanol. The invention aims to reduce 3-(3-trifluoromethylphenyl)propionic acid to 3-(3'-trifluoromethyl phenyl)propanol with a simple and efficient method.
Between the synthesis of trifluoromethyl phenylpropanol (by machine translation)
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Paragraph 0008; 0009; 0010, (2017/11/16)
The present invention provides a hydrogenation reduction preparation trifluoromethyl phenylpropanol method. In the high pressure autoclave, incendiary as solvent, adding meta-trifluoromethyl cinnamyl alcohol, according to three fluorine methyl cinnamyl alcohol of the mass fraction of 5% - 30% proportion of hydrogenation catalyst KT - 02, to the high-pressure seal is nitrogen after the replacement, the hydrogen gas to the pressure 0.5 - 3.0 mpa and heating to 40 - 100 °C reaction 4 - 15 hours, can be trifluoromethyl cinnamic alcohol between fully converted to three fluorine methyl carbonate, and the product yield of the product can be up to 99% or more. The hydrogenation catalyst used in this invention KT - 02 and the price is low, stable, and safe operation, in order to its as a hydrogenation catalyst after the reaction is finished and convenient product separation. Synthesis method of the invention will be more suitable for industrialized production between trifluoromethyl phenylpropanol. (by machine translation)
Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C?C Bond Formation
Shimogaki, Mio,Fujita, Morifumi,Sugimura, Takashi
, p. 15797 - 15801 (2016/12/16)
The enantioselective oxyarylation of (E)-6-aryl-1-silyloxylhex-3-ene was achieved using a lactate-based chiral hypervalent iodine(III) reagent in the presence of boron trifluoride diethyl etherate. The silyl ether promotes the oxidative cyclization, and enhances the enantioselectivity. In addition, the corresponding aminoarylation was achieved.
A plug intermediate body west that card 3 - (3-trifluoromethyl phenyl) propanol method for the synthesis of (by machine translation)
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Paragraph 0017, (2016/11/17)
The invention discloses a plug intermediate body west that card 3 - (3-trifluoromethyl phenyl) propanol synthetic method, including: the trifluoromethyl benzaldehyde dissolved in a solvent, adding wittig agents and organic alkali, in 0-100 °C under a temperature condition after the reaction is complete, the post-processed to obtain 3 - (3-trifluoromethyl phenyl) 2-propen -1 alcohol; to 3 - (3-trifluoromethyl phenyl) 2-propen -1 catalyst Pd/C alcohol solution added in, and pressurized hydrogenation, in 0-60 °C under a temperature condition after the reaction is complete, the post-processed to obtain 3 - (3-trifluoromethyl phenyl) propanol. The preparation process of the present invention the easily obtained raw material used, the cost is low, and the reaction is controllable, the test operation is simplified, the operation is simple, is easy to deal with, high yield of the product, and can be operated continuously, is suitable for industrial production. (by machine translation)
