80227-68-5Relevant academic research and scientific papers
Green preparation method of aryl diselenium ether type organic selenium compound
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Paragraph 0052-0056, (2021/11/14)
The invention discloses an aryl diselenium ether compound synthesis method. The synthesis method comprises the following steps: taking the compound represented by the formula (I) as a reaction raw material, CuBr as a catalyst, KOH in the condition Se, a reducing agent, a disproportionation reaction, water or ethanol as a solvent, and 60 °C. After completion of the reaction, the obtained reaction solution is subjected to post-treatment (if ethanol is recovered as solvent) to obtain the aryl diselenoether compound represented by the formula (II), the yield is close 100%, the subsequent treatment is simple, and a complex separation and purification method is not needed to obtain a pure product. The solvent is recovered as a solvent such as ethanol. , It is preferable. The method is more green. Economy, high efficiency, environmental protection.
Lead optimization generates selenium-containing miconazole CYP51 inhibitors with improved pharmacological profile for the treatment of fungal infections
Xu, Hang,Yan, Zhong-zuo,Guo, Meng-bi,An, Ran,Wang, Xin,Zhang, Rui,Mou, Yan-hua,Hou, Zhuang,Guo, Chun
, (2021/03/16)
A series of selenium-containing miconazole derivatives were identified as potent antifungal drugs in our previous study. Representative compound A03 (MIC = 0.01 μg/mL against C.alb. 5314) proved efficacious in inhibiting the growth of fungal pathogens. However, further study showed lead compound A03 exhibited potential hemolysis, significant cytotoxic effect and unfavorable metabolic stability and was therefore modified to overcome these drawbacks. In this article, the further optimization of selenium-containing miconazole derivatives resulted in the discovery of similarly potent compound B17 (MIC = 0.02 μg/mL against C.alb. 5314), exhibiting a superior pharmacological profile with decreased rate of metabolism, cytotoxic effect and hemolysis. Furthermore, compound B17 showed fungicidal activity against Candida albicans and significant effects on the treatment of resistant Candida albicans infections. Meanwhile, compound B17 not only could reduce the ergosterol biosynthesis pathway by inhibiting CYP51, but also inhibited biofilm formation. More importantly, compound B17 also shows promising in vivo efficacy after intraperitoneal injection and the PK study of compound B17 was evaluated. In addition, molecular docking studies provide a model for the interaction between the compound B17 and the CYP51 protein. Overall, we believe that these selenium-containing miconazole compounds can be further developed for the potential treatment of fungal infections.
Nickel-Catalyzed Intramolecular Decarbonylative Coupling of Aryl Selenol Esters
Bai, Jin-Hua,Qi, Xiu-Juan,Sun, Wei,Yu, Tian-Yang,Xu, Peng-Fei
supporting information, p. 2084 - 2088 (2021/03/01)
This report describes a method for Ni-catalyzed intramolecular decarbonylative coupling, which enables the conversion of areneselenol esters to diaryl selenides. The inexpensive and readily available catalyst can be employed under mild reaction conditions for the construction of structurally diverse diaryl selenides, including heterocyclic and natural product derivatives. (Figure presented.).
Rhodium-Catalyzed Enantioselective Hydroselenation of Heterobicyclic Alkenes
Li, Sifeng,Yang, Qingjing,Bian, Zhaoxiang,Wang, Jun
supporting information, p. 2781 - 2785 (2020/03/30)
A highly efficient Rh(I)/(S)-xyl-Binap catalytic system is developed for the asymmetric hydroselenation of various nonpolar olefins with diselenides. Under these mild reaction conditions, a wide range of heterobicyclic alkenes give selenol-incorporated adducts in excellent enantioselectivities (up to 97%) along with high yields (up to 96%) by overcoming self-promoted racemic hydroselenation. The strategy is also applied for kinetic resolution of unsymmetric oxabenzonorbornadiene.
Metal-Free ipso -Selenocyanation of Arylboronic Acids Using Malononitrile and Selenium Dioxide
Broggi, Julie,Kosso, Anne Roly Obah,Redon, Sébastien,Vanelle, Patrice
supporting information, p. 3758 - 3764 (2019/09/30)
The first ipso -selenocyanation of arylboronic acids is achieved using selenium dioxide and malononitrile under mild conditions. The reaction is successful even without metal or base in DMSO. The major advantages of this new method are an easy set-up, excellent yields, and the use of odorless and inexpensive selenium reagents. Basic conditions subsequently afford new access to diaryldiselenides in good yields without isolating the organoselenocyanate intermediates.
Trifluoromethylthiolative 1,2-difunctionalization of alkenes with diselenides and AgSCF3
Saravanan, Perumal,Anbarasan, Pazhamalai
supporting information, p. 4639 - 4642 (2019/05/02)
An efficient regioselective difunctionalization of alkenes via trifluoromethylthiolation has been accomplished employing diaryl diselenide and AgSCF3 in the presence of BF3·OEt2. Various substituted 1,2-dichalcogenated products having the SCF3 moiety were synthesized in good to excellent yields under mild conditions. The preliminary mechanistic investigation revealed the possible reaction pathway and unique combination of diselenide and AgSCF3 for successful transformation.
One-pot preparation of (RSe)2CF2 and (RS)2CF2 compounds via insertion of TMSCF3-derived difluorocarbene into diselenides and disulfides
Barrett, Colby,Krishnamurti, Vinayak,Oliveira, Artur Pratas,Prakash, G.K. Surya
, p. 4167 - 4173 (2019/04/30)
A method for the first direct insertion of difluorcarbene, generated from TMSCF3, into diselenides and disulfides is disclosed, producing novel difluoromethyl diselenoacetals and difluoromethyl dithioacetals. The reaction conditions tolerate a range of synthetically useful and biologically relevant functional groups. The process is scalable, with two representative compounds prepared at a gram-scale in good yields, and it utilizes cheap and available reagents.
CuO nanoparticles-catalyzed a novel method to the synthesis of symmetrical diselenides from aryl halides: selenoamide as an organic Se-donor reagent
Soleiman-Beigi, Mohammad,Yavari, Issa,Sadeghizadeh, Fatemeh
, p. 2239 - 2246 (2018/08/04)
A new method is reported for the synthesis of symmetrical diaryldiselenides from aryl halides using selenoamide as an organic Se-donor reagent in the presence of copper (II) oxide nanoparticles. CuO nanoparticles were found to be an efficient and inexpensive catalyst for ligand-free C-Se bond formation with a series of symmetrical diaryldiselenides obtained in good to excellent yield.
Mechanistic Studies on the Anodic Functionalization of Alkenes Catalyzed by Diselenides
Wilken, Mona,Ortgies, Stefan,Breder, Alexander,Siewert, Inke
, p. 10901 - 10912 (2018/11/02)
Herein, we present a detailed kinetic and thermodynamic analysis of the anodic allylic esterification of alkenes as well as the bulk application of the anodic amination and esterification of nonactivated alkenes catalyzed by diselenides. The electrochemical study led to a comprehensive picture of the coupled electrochemical and chemical reaction steps. Cyclic voltammetry measurements are consistent with a bimolecular step after initial electrochemical 1e- oxidation of the diphenyl diselenide catalyst, 1a, and therefore we postulate a dimerization of the cation, which reacts very rapidly with the alkene, forming the addition product, i.e. the selenolactone 2a. Subsequent electrochemical oxidation of 2a occurs at a slightly higher potential than initial oxidation of 1a. The second oxidation is also followed by a bimolecular process and we hypothesize a dimerization of the cation, which finally eliminates 1a and protons in the rate-determining step, forming the product. Electrochemical analysis of various catalysts, i.e. nonsterically demanding diaryl diselenides with electron withdrawing and donating substituents, revealed that the oxidation potential of the catalyst and the intermediate can be readily tuned by the substituents, thus, prospectively allowing for a wide application of olefinic and nucleophilic substrates. The substituent pattern at the alkene has a smaller influence on the redox potential of the adduct. Controlled potential electrolysis experiments employing different nucleophiles proved that the reaction can be run electrochemically. The functionalization of unactivated alkenes with N- and O-nucleophiles was successfully demonstrated in several bulk electrolysis experiments, and the products were isolated in good yields.
Aerobic Allylation of Alcohols with Non-Activated Alkenes Enabled by Light-Driven Selenium-π-Acid Catalysis
Rode, Katharina,Palomba, Martina,Ortgies, Stefan,Rieger, Rene,Breder, Alexander
supporting information, p. 3875 - 3885 (2018/09/29)
A new organocatalytic protocol for the aerobic dehydrogenative allylation of alcohols using non-activated alkenes as the allylating reagent and ambient air as the terminal oxidant is established. Mechanistically, the procedure relies on the interplay of a diselane and a photoredox catalyst by means of a light-induced electron transfer process. Under optimized conditions, a broad range of both cyclic and acyclic ethers is accessed with very high functional group tolerance and excellent regioselectivity.
