27798-73-8Relevant academic research and scientific papers
Preparation method of carboxylic ester compound
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Paragraph 0061-0062, (2021/03/30)
The invention relates to a preparation method of a carboxylic ester compound, which comprises the following steps: reacting carboxylic acid with methanol in air under the catalysis of nitrite to obtain an ester compound, the preparation method disclosed by the invention has the advantages of rich raw material sources, cheap and easily available catalyst, mild reaction conditions, simplicity and convenience in operation and the like, a series of fatty carboxylic acids can be modified with high yield, and particularly, the traditional esterification method is generally not suitable for esterification of drug molecules. By utilizing the method, a series of known drug molecules can be modified, so that a shortcut is provided for discovering new drug molecules.
Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite
Cheng, Xionglve,Jiang, Gangzhong,Li, Xingxing,Tao, Suyan,Wan, Xiaobing,Zhao, Yanwei,Zheng, Yonggao
supporting information, p. 2713 - 2718 (2021/06/25)
In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.
Copper-Catalyzed Intermolecular Enantioselective Radical Oxidative C(sp3)?H/C(sp)?H Cross-Coupling with Rationally Designed Oxazoline-Derived N,N,P(O)-Ligands
Gu, Qiang-Shuai,Guo, Kai-Xin,Li, Zhong-Liang,Liu, Lin,Liu, Xin-Yuan,Tian, Yu,Yang, Chang-Jiang,Ye, Liu
supporting information, p. 26710 - 26717 (2021/11/18)
The intermolecular asymmetric radical oxidative C(sp3)?C(sp) cross-coupling of C(sp3)?H bonds with readily available terminal alkynes is a promising method to forge chiral C(sp3)?C(sp) bonds because of the high atom and step economy, but remains underexplored. Here, we report a copper-catalyzed asymmetric C(sp3)?C(sp) cross-coupling of (hetero)benzylic and (cyclic)allylic C?H bonds with terminal alkynes that occurs with high to excellent enantioselectivity. Critical to the success is the rational design of chiral oxazoline-derived N,N,P(O)-ligands that not only tolerate the strong oxidative conditions which are requisite for intermolecular hydrogen atom abstraction (HAA) processes but also induce the challenging enantiocontrol. Direct access to a range of synthetically useful chiral benzylic alkynes and 1,4-enynes, high site-selectivity among similar C(sp3)?H bonds, and facile synthesis of enantioenriched medicinally relevant compounds make this approach very attractive.
Aldehyde as a Traceless Directing Group for Regioselective C-H Alkylation Catalyzed by Rhodium(III) in Air
Chen, Si-Qi,Fan, Juan,Li, Chao-Jun,Li, Xin-Ran,Liu, Zhong-Wen,Shi, Xian-Ying
supporting information, p. 1259 - 1264 (2020/03/13)
The aromatic aldehyde as a traceless directing group for the regionselective C-H alkylation catalyzed by rhodium(III) under aerobic atmospheric conditions has been developed. The process involves an aldehyde assisted direct addition of C-H bond to unsaturated electrophiles of acrylates or acrylic acids, and the subsequent decarbonylation. A trace amount of water is found to favor the reaction.
Synthesis method of dihydrocinnamate type compound
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Paragraph 0014-017; 0050-0053, (2019/03/30)
The invention discloses a synthesis method of a dihydrocinnamate type compound. The method takes a dichloro(pentamethylcyclopentadienyl)rhodium dimer as a catalyst and a formyl o-C-H bond of aromaticaldehyde and alpha,beta-unsaturated ester type compound
Synthesis, in vitro and in silico evaluation of diaryl heptanones as potential 5LOX enzyme inhibitors
Meka, Bharani,Ravada, Suryachandra Rao,Muthyala, Murali Krishna Kumar,Kurre, Purna Nagasree,Golakoti, Trimurtulu
, p. 408 - 421 (2018/07/13)
A new series of diaryl heptanones (12a-q) were synthesized and their structures were confirmed by its 1H, 13C NMR and Mass spectral data. These analogs were evaluated for their anti-oxidant activity and potential to inhibit 5-lipoxygenase. Compounds 12k and 12o showed potent in vitro 5-lipoxygenase enzyme inhibitory activity with IC50 values of 22.2, 21.5 μM, which are comparable to curcumin (24.4 μM). Further they also have shown significant antioxidant activity. Molecular docking studies clearly showed correlation between binding energy and potency of these compounds.
Comparison of Phenylacetates with Benzoates and Phenylpropanoates as Antifeedants for the Pine Weevil, Hylobius abietis
Unelius, C. Rikard,Bohman, Bj?rn,Nordlander, G?ran
, p. 11797 - 11805 (2018/11/21)
This study concludes an extensive investigation of antifeedants for the pine weevil, Hylobius abietis (Coleoptera: Curculionidae), an economically important pest of planted conifer seedlings. Building on the previously reported antifeedant effects of benzoates and phenylpropanoids (aromatic compounds with one- or three-carbon-atom substituents on the benzene ring), we here report the antifeedant effects of compounds with two-carbon-atom side chains (i.e., phenylacetates). We also present new results; the best antifeedants from the benzoate class were tested at 10-fold lower concentrations in order to find the optimal antifeedants. Generally, for all three compound classes, efficient antifeedants were found to have one or two methyl, chloro, or methoxy substituents on the aromatic ring. For monosubstituted phenylpropanoids, the substituent preferably should be in the para-position. In the search for synergistic antifeedant effects among the three compound classes, combinations of compounds from the three classes were tested in binary and ternary mixtures.
7. 8 - dimethoxy - 2, 3, 4, 5 - tetrahydro - 1 H - benzo [c] azepine hydrochloride and its preparation method (by machine translation)
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Paragraph 0017; 0027; 0035, (2017/11/16)
The invention discloses 7, 8 - dimethoxy - 2, 3, 4, 5 - tetrahydro - 1 H - benzo [c] azepine hydrochloride and its preparation method, in order to 3, 4 - dimethoxy c acid as initiator, in thionyl chloride catalytic, then ammonolysis to obtain 3, 4 - dimet
Mild Esterification of Carboxylic Acids via Continuous Flow Diazotization of Amines
Audubert, Clément,Lebel, Hélène
supporting information, p. 4407 - 4410 (2017/08/23)
A new continuous flow protocol for the diazotization of methylamine with 1,3-propanedinitrite in THF is reported. The synthesis of methyl esters was achieved in high yields from a variety of carboxylic acids in 20 min at 90 °C. Additionally, this protocol was extended to other aryl and alkyl amines, namely secondary amines, to produce various substituted esters in high yield using 2-MeTHF as a solvent. The reaction conditions were compatible with many functional groups, namely nitrogen-containing heterocycles, alkynes, alkenes, alcohols, and phenols. Mechanistic investigations reveal that the reaction appears to proceed through a transient diazonium species rather than a diazo intermediate.
Batch and Continuous-Flow One-Pot Processes using Amine Diazotization to Produce Silylated Diazo Reagents
Audubert, Clément,Gamboa Marin, Oscar Javier,Lebel, Hélène
supporting information, p. 6294 - 6297 (2017/05/19)
A novel synthesis of trimethylsilyldiazomethane (TMSCHN2) by diazotization of trimethylsilylmethylamine (TMSCH2NH2) is reported using batch and continuous flow synthesis. The latter affords a daily production of 275 g (2.4 mol) of TMSCHN2. Other silylated methylamines were also successfully reacted under the developed reaction conditions to furnish various silicon-bearing diazomethane reagents. The applicability of the process is highlighted by disclosure of batch and continuous flow one-pot esterification and 1,3-dipolar cycloaddition processes. Furthermore, the high-yielding esterification of carboxylic acids with silylated and substituted methylamines in continuous flow is disclosed. Finally, work-up and purification procedures are reported for the preparation of a 2-MeTHF solution of TMSCHN2, which can be used in rhodium-catalyzed methylenation and homologation reactions.
