6962-92-1Relevant articles and documents
Merging structural frameworks of imidazolium, pyridinium, and cholinium ionic liquids with cinnamic acid to tune solution state behavior and properties
Ananikov, Valentine P.,Egorova, Ksenia S.,Gordeev, Evgeniy G.,Posvyatenko, Alexandra V.,Seitkalieva, Marina M.,Strukova, Elena N.,Vavina, Anna V.
, (2022/03/14)
Solubility in water, interactions with the solvent medium and tuning of molecular conformation in the liquid phase are the key issues to discover new biologically active molecules and to understand the mechanisms of their action. In the present article, we report synthesis, structural and biological activity studies, and computational modeling of new ionic compounds. Structural frameworks of well-known imidazolium, pyridinium and cholinium ionic liquids (ILs) were combined with naturally occurring cinnamic acid (CA), which is known to possess a wide spectrum of biological activity. Different combinations of these two structural elements (IL and Cin (cinnamic moiety)) allowed modulating the solubility, physicochemical properties and biological activity of the resulting molecules. A significant increase in the biological activity was achieved for the three studied hybrid molecules - [C4mim-Cin][Cl], [C4py–Cin][Cl], and [C4mim-Cin][Cin]. Multiparameter cytotoxicity mapping was performed to visualize the biological activity of the 28 studied molecules. Detailed experimental investigation and molecular dynamics simulation were performed to gain insight into the structure–activity relationship. Of note, a folding conformational change in the structure of [Cnmim-Cin][Cl] hybrid molecules in solution resulted in a substantial change in chemical reactivity, with the activation energy of the hydrolysis reaction decreasing from 32.1 to 23.9 kcal/mol.
Synthesis of chloroesters by the reaction of ethers with acyl chlorides catalyzed by ZnO
Tang, Yuqi,Feng, Chengliang,Yang, Wanfeng,Ji, Min,Wang, Wei,Chen, Junqing
, p. 1 - 8 (2020/07/13)
An efficient method for the synthesis of chloroesters by the reaction of ethers with acyl chlorides catalyzed by nano-ZnO under solvent-free condition at room temperature was described. The method is compatible with a range of ethers including tricyclic ethers, tetracyclic ethers, pentacyclic ethers and hexacyclic ethers and have afforded the products with moderate to good yields. The ZnO could be reused up to three times and the product yield after three cycles is 87%.
Practical and Selective sp3 C?H Bond Chlorination via Aminium Radicals
McMillan, Alastair J.,Sieńkowska, Martyna,Di Lorenzo, Piero,Gransbury, Gemma K.,Chilton, Nicholas F.,Salamone, Michela,Ruffoni, Alessandro,Bietti, Massimo,Leonori, Daniele
supporting information, p. 7132 - 7139 (2021/03/03)
The introduction of chlorine atoms into organic molecules is fundamental to the manufacture of industrial chemicals, the elaboration of advanced synthetic intermediates and also the fine-tuning of physicochemical and biological properties of drugs, agrochemicals and polymers. We report here a general and practical photochemical strategy enabling the site-selective chlorination of sp3 C?H bonds. This process exploits the ability of protonated N-chloroamines to serve as aminium radical precursors and also radical chlorinating agents. Upon photochemical initiation, an efficient radical-chain propagation is established allowing the functionalization of a broad range of substrates due to the large number of compatible functionalities. The ability to synergistically maximize both polar and steric effects in the H-atom transfer transition state through appropriate selection of the aminium radical has provided the highest known selectivity in radical sp3 C?H chlorination.
Synthesis, in silico study and antimicrobial activity of new piperine derivatives containing substituted δ-esters
Barbosa-Filho, José M.,Brandao, Maria C. R.,De Athayde-Filho, Petr?nio F.,Dutra, Thalisson F.,Lima, Edeltrudes O.,Lira, Bruno F.,Neto, Hermes Diniz,Trindade, Emmely O.
, p. 2590 - 2602 (2020/11/18)
A series of fifteen new piperine-derived diesters was synthesized through the substitution reaction between the salt of piperic acid, obtained through piperine basic hydrolysis, with the δ-chloro-esters, obtained through the cleavage of tetrahydrofuran (THF) with acyl chlorides in the presence of ZnCl2. The final compounds were obtained with yields ranging from 50 to 84% and were characterized by infrared (IR) and 1H and 13C nuclear magnetic resonance spectroscopy (NMR). The new compounds were evaluated in silico in regard to their ADME (absorption, distribution, metabolism, and excretion) properties, and in vitro for their antimicrobial activity against bacteria strains (Staphylococcus aureus and Pseudomonas aeruginosas), yeast fungi (Candida albicans and C. tropicalis) and filamentous fungi (Aspergillus fumigatus, A. flavus and A. niger). The results from the in silico studies of Lipinski's rule of five showed that most compounds present good pharmacological possibilities, and the results from in vitro antimicrobial activity showed that 8 of the 15 synthesized compounds displayed antimicrobial activity, inhibiting the growth of 40-80% of tested strains, with a minimum inhibitory concentration (MIC) interval ranging from 1024 to 256 μg mL-1
Preparation method and application of alkyl ether sulfonyl fluoride compound
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Paragraph 0102-0106, (2020/08/22)
The invention belongs to the technical field of chemical synthesis methods, and particularly relates to a preparation method of an alkyl ether sulfonyl fluoride compound. The preparation method comprises the following steps: reacting an alkyl ether sodium sulfonate compound with a chlorination reagent to obtain an alkyl ether sulfonyl chloride compound; and reacting the alkyl ether sulfonyl chloride compound with a nucleophilic fluorination reagent to obtain the alkyl ether sulfonyl fluoride compound. A preparation method for the alkyl ether sodium sulfonate compound comprises the following steps: (1) reacting tetrahydrofuran with acetyl chloride to obtain 4-chlorobutyl acetate; (2) carrying out a sulfonation reaction on the 4-chlorobutyl acetate obtained in the step (1) and sodium sulfiteto obtain sodium 4-hydroxybutanesulfonate; and (3) reacting the sodium 4-hydroxybutanesulfonate obtained in the step (2) with sodium hydroxide and brominated alkane to obtain the alkyl ether sodium sulfonate compound. The alkyl ether sulfonyl fluoride compound obtained by using the preparation method can be used as a precursor of an existing perfluorochemical, and has the characteristics that thealkyl ether sulfonyl fluoride compound is easy to degrade, degraded substances have lower toxicity or bioaccumulation and the like.
Synthesis method of 1,4-butane sultone
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Paragraph 0010; 0030-0032; 0036-0038; 0042-0044, (2019/06/12)
The invention relates to a synthesis method of 1,4-butane sultone and belongs to the technical field of compound synthesis. The synthesis method takes tetrahydrofuran and acetylchloride as raw materials and comprises the following steps: A, preparation of butylchloroacetate: placing tetrahydrofuran and zinc powder in a container, cooling to 15 DEG C or lower, beginning to dropwise add acetylchloride, after dropwise adding, heating to 45 DEG C, holding the temperature for 8-10 hours, then heating to 60 DEG C, holding the temperature for 1-2 hour, performing pressure reduction to extract butylchloroacetate, and B, preparation of 1,4-butane sultone: allowing butylchloroacetate, sodium sulfite and water to give a heating reflux reaction for 14-16 hour, performing pressure reduction till a solid is separated out, cooling to 45 DEG C or lower, dropwise adding methanol hydrochloride solution, performing stirring for 1-2 hours, cooling to 4-6 DEG C, performing suction filtration, performing pressure reduction on filtrate to extract methanol, water and acetic acid, then heating to 130 DEG C, performing high vacuum pressure reduction cyclization for 0.5-1 hour, heating to 150 DEG C, and thenperforming high vacuum pressure reduction to extract 1,4-butane sultone. The synthesis method is simple; a reaction process is mild and stable; a prepared target product is high in yield and purity,and very low in water content and acid content.
Preparation method of 4-halobutyl acetate
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Paragraph 0054-0062; 0068-0069; 0072, (2018/09/20)
The invention discloses a preparation method of 4-halobutyl acetate, relates to the preparation method of acetate and aims to solve the technical problems that in an existing method for preparing the4-halobutyl acetate, the reaction time is long, the reaction temperature is high, the cost is high, a toxic reagent is used, the operation is complicated, and the yield is low. The preparation methodcomprises the following steps: mixing and stirring urea, tetrahydrofuran and acetyl halide, naturally cooling to room temperature, adding distilled water, regulating pH (Potential of Hydrogen) to be neutral, carrying out suction filtration, extracting, drying, filtering, and distilling. The 4-halobutyl acetate prepared by the invention structurally contains an ester group and chain end halogen andis a multi-purpose polyfunctional compound. The 4-halobutyl acetate prepared by the invention is prepared from corresponding acyl halide and cyclic ether under catalysis of the urea, and the preparation method is bran-new. A solid byproduct of the preparation method is acyl urea. The preparation method disclosed by the invention has the advantages of simple operation, low cost, safety and high efficiency, environment friendliness and the like.
Palladium(II) acetate catalyzed acylative cleavage of cyclic and acyclic ethers under neat conditions
Fotie, Jean,Adolph, Brandy R.,Bhatt, Shreya V.,Grimm, Casey C.
supporting information, p. 4648 - 4651 (2017/11/15)
During the development of a palladium catalyzed C–H activation cross-coupling reaction involving acyl halides, it was noted that palladium(II) acetate catalyzes the acylative cleavage of tetrahydrofuran (used as a solvent) at room temperature to afford the corresponding 4-chlorobutyl ester derivative. After optimization, the reaction was shown to work well with epoxides, oxetane and tetrahydrofuran, but only barely with oxanes at room temperature. Acyclic ethers systematically failed to react under similar conditions, but underwent complete conversion in a microwave reactor at 100 °C.
COMPOUND APPLICABLE TO PHOTOALIGNMENT METHOD AND ITS PHOTOSENSITIVE POLYMER
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Paragraph 0256-0260, (2017/09/29)
PURPOSE: A photosensitive polymer prepared by polymerizing a compound which is proper for photoalignment is provided to prevent static electricity and to manufacture liquid crystal alignment film with high optical uniformity. CONSTITUTION: A compound which is proper to photoalignment is denoted by chemical formula 1. A photosensitive polymer is used by polymerizing the compound of chemical formula 1. A liquid crystal alignment film is manufactured using the photoalignment agent. A liquid crystal display device is manufactured using the photoalignment agent.