42792-79-0Relevant academic research and scientific papers
2,6-bis(E)-4-methylbenzylidine)-cyclohexan-1-one as a Fluorescent-on Sensor for Ultra Selective Detection of Chromium Ion in Aqueous Media
Khan, Jehangir,Sadia, Maria,Shah, Syed Wadood Ali,Naz, Robina,Ali, Faiz
, p. 1759 - 1770 (2021/09/11)
Abstract: The ligand 2,6-bis(E)-4-methylbenzylidine)-cyclohexan-1-one sensor has been synthesized as a fluorescence-on sensor/probe for the trace level detection of chromium III ion. The synthesized ligand was characterized by FTIR, 1H-NMR spec
Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water
Tanemura, Kiyoshi,Rohand, Taoufik
supporting information, (2021/02/27)
A variety of chalcones were synthesized in good yields by the activated charcoal-mediated aldol reactions between benzaldehydes and acetophenones catalyzed by NaOH in water. 2,6-Bis((E)-benzylidene)cyclohexan-1-ones were prepared by the aldol reactions between benzaldehydes and cyclohexanone. Activated charcoal could be recycled five times without the significant decrease of yields.
Synthesis of lithium/cesium-Zagronas from zagrosian natural asphalt and study of their activity as novel, green, heterogeneous and homogeneous nanocatalysts in the Claisen–Schmidt and Knoevenagel condensations
Soleiman-Beigi, Mohammad,Ghalavand, Saba,Venovel, Hadis Gholami,Kohzadi, Homa
, p. 3267 - 3279 (2021/06/17)
A novel, heterogeneous and homogeneous basic nanocatalysts were synthesized by grafting of lithium and cesium on zagrosian natural asphalt sulfonate (Li/Cs-Zagronas). The activity of these catalysts was examined in the Claisen–Schmidt and Knoevenagel condensations under mild reaction conditions. Li/Cs-Zagronas were characterized by FT-IR spectroscopy, scanning electron microscopy, X-ray diffraction, energy-dispersive spectroscopy, inductively coupled plasma and thermogravimetric analysis techniques. These nanocatalysts were removed by simple filtration and reused several times without any deterioration of activity.
Green, rapid, and highly efficient syntheses of α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones as potentially biologic compounds via solvent-free microwave-assisted Claisen–Schmidt condensation catalyzed by MoCl5
Bakhshi, Reza,Zeynizadeh, Behzad,Mousavi, Hossein
, p. 623 - 637 (2019/08/26)
A new, green, and highly efficient protocol for the expeditious preparation of some α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones via a simple microwave-assisted Claisen–Schmidt condensation reaction catalyzed by MoCl5 was successfully developed. Outstanding features of the current methodology include the use of solvent-free conditions, simple operation, use of a very inexpensive and available catalyst, low catalyst loading, short reaction times, high yields of the pure products, no harmful by-products, easy workup, and also the applicability of microwave irradiation as a clean source of energy. Furthermore, a gram-scale reaction was successfully conducted, proving the scalability of this current Claisen–Schmidt condensation reaction.
Potassium Natural Asphalt Sulfonate (K-NAS): Synthesis and characterization as a new recyclable solid basic nanocatalyst and its application in the formation of carbon–carbon bonds
Falah, Saeid,Soleiman-Beigi, Mohammad,Kohzadi, Homa
, (2020/07/06)
In this research, we synthesized and characterized a new heterogeneous basic nanocatalyst and its catalytic application was studied in the Claisen-Schmidt and Knoevenagel condensations. In order to prepare this nanocatalyst, first, the Iranian natural asphalt was sulfonated with the concentrated sulfuric acid and then, converted to the potassium natural asphalt sulfonate (K-NAS). In order to characterization of the nanocatalyst, used of FT-IR spectroscopy, scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), X-ray diffraction (XRD), inductively coupled plasma (ICP) and thermogravimetric analysis (TGA) techniques. This new basic heterogeneous nanocatalyst have advantages such as being eco-friendly, huge specific surface area, high reactivity and recyclability.
Antiparasitic activity of synthetic curcumin monocarbonyl analogues against Trichomonas vaginalis
Carapina da Silva, Caroline,Pacheco, Bruna Silveira,das Neves, Raquel Nascimento,Dié Alves, Mirna Samara,Sena-Lopes, ?ngela,Moura, Sidnei,Borsuk, Sibele,de Pereira, Claudio Martin Pereira
, p. 367 - 377 (2019/01/03)
Trichomoniasis is a parasitic infection caused by Trichomonas vaginalis and it is considered to be the most common non-viral sexually transmitted infection in the world. Since the 1960s, nitroimidazoles such as metronidazole are the drugs of choice for the treatment of trichomoniasis, but many adverse effects and allergic reactions may result from their use. Reports of metronidazole-resistant infections also highlight the importance for the search of new anti-T. vaginalis agents. Considering this, herein we report the anti-T. vaginalis evaluation of 21 synthetic monocarbonyl analogues of curcumin, which itself has been reported to possess antiparasitic potential. From the in vitro analysis of the synthetic molecules, untreated trophozoites, and metronidazole at 100 μM, it was observed that three curcumin analogues (3a, 3e, and 5e) exhibited anti-T. vaginalis activity comparable to metronidazole (no significant statistical difference). Optimal antiparasitic concentrations were determined to be 80 μM and 90 μM for propanone derivatives 3a and 3e, respectively, and 200 μM for cyclohexanone derivative 5e. Kinetic growth curves showed that, after 24 h, the trophozoites were completely inhibited. At the tested concentrations, natural curcumin did not significantly inhibit the growth of trophozoites, therefore demonstrating that the designed synthetic molecules not only have better chemical stability, but also higher anti-T. vaginalis potential. Cytotoxicity analysis, performed on VERO cells, demonstrated low, moderate and high cytotoxic effects for analogues 3e, 5e and 3a, respectively. This study suggests that these analogues possess chemical features of interest to be further explored as alternatives for the treatment of trichomoniasis.
Ag/P-Stereogenic Phosphine-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions: A Method to Optically Active Pyrrolidines
Zhi, Mengna,Gan, Zhenjie,Ma, Rong,Cui, Hao,Li, Er-Qing,Duan, Zheng,Mathey, Fran?ois
supporting information, (2019/05/07)
A Ag/P-stereogenic phosphine-complex-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with electron-deficient olefins is reported. In this reaction, highly functionalized pyrrolines with a spiro-quaternary stereogenic center were obtained in good yields (up to 99%) with excellent levels of diastereo-(up to >20:1 dr) and enantioselectivities (up to >99% ee). The chirality of adducts was controlled predominantly by the P-stereogenic phosphines.
Chiral Cyclohexyl-Fused Spirobiindanes: Practical Synthesis, Ligand Development, and Asymmetric Catalysis
Zheng, Zhiyao,Cao, Yuxi,Chong, Qinglei,Han, Zhaobin,Ding, Jiaming,Luo, Chenguang,Wang, Zheng,Zhu, Dongsheng,Zhou, Qi-Lin,Ding, Kuiling
supporting information, p. 10374 - 10381 (2018/08/03)
1,1′-Spirobiindane has been one type of privileged skeleton for chiral ligand design, and 1,1′-spirobiindane-based chiral ligands have demonstrated outstanding performance in various asymmetric catalysis. However, the access to enantiopure spirobiindane is quite tedious, which obstructs its practical application. In the present article, a facile enantioselective synthesis of cyclohexyl-fused chiral spirobiindanes has been accomplished, in high yields and excellent stereoselectivities (up to >99% ee), via a sequence of Ir-catalyzed asymmetric hydrogenation of α,α′-bis(arylidene)ketones and TiCl4 promoted asymmetric spiroannulation of the hydrogenated chiral ketones. The protocol can be performed in one pot and is readily scalable, and has been utilized in a 25 g scale asymmetric synthesis of cyclohexyl-fused spirobiindanediol (1S,2S,2′S)-5, in >99% ee and 67% overall yield for four steps without chromatographic purification. Facile derivations of (1S,2S,2′S)-5 provided straightforward access to chiral monodentate phosphoramidites 6a-c and a tridentate phosphorus-amidopyridine 11, which were evaluated as chiral ligands in several benchmark enantioselective reactions (hydrogenation, hydroacylation, and [2 + 2] reaction) catalyzed by transition metal (Rh, Au, or Ir). Preliminary results from comparative studies showcased the excellent catalytic performances of these ligands, with a competency essentially equal to the corresponding well-established privileged ligands bearing a regular spirobiindane backbone. X-ray crystallography revealed a close resemblance between the structures of the precatalysts 20 and 21 and their analogues, which ultimately help to rationalize the almost identical stereochemical outcomes of reactions catalyzed by metal complexes of spirobiindane-derived ligands with or without a fused cyclohexyl ring on the backbone. This work is expected to stimulate further applications of this type of readily accessible skeletons in development of chiral ligands and functional molecules.
Synthesis of high-density aviation fuels with methyl benzaldehyde and cyclohexanone
Xu, Jilei,Li, Ning,Li, Guangyi,Han, Fengan,Wang, Aiqin,Cong, Yu,Wang, Xiaodong,Zhang, Tao
supporting information, p. 3753 - 3760 (2018/08/22)
A new two-step process was developed for the synthesis of high-density jet fuel range tricyclic alkanes with methyl benzaldehydes and cyclohexanone which can be derived from lignocellulose. In the first step, C14 oxygenates (i.e. 2-(2-methylbenzylidene)cyclohexanone or 2-(4-methylbenzylidene)cyclohexanone) were obtained by the solvent-free aldol condensation of 2-methyl benzaldehyde (or 4-methyl benzaldehyde) and cyclohexanone. Among the investigated catalysts, the EAOAc ionic liquid (a renewable catalyst which was prepared with ethanolamine and acetic acid) exhibited the highest activity and good stability for this reaction. Over it, high carbon yields (～85%) of C14 oxygenates were achieved under mild reaction conditions (353 K, 6 h). In the second step, the C14 oxygenates were selectively converted into 1-methyldodecahydro-1H-fluorene and 3-methyldodecahydro-1H-fluorene by the aqueous phase hydrodeoxygenation (APHDO) over a commercial Pd/C catalyst. According to our measurement, the 1-methyldodecahydro-1H-fluorene and 3-methyldodecahydro-1H-fluorene as obtained have high densities (0.99 g mL-1 and 0.96 g mL-1, respectively, at 298 K). As a potential application, they can be used as additives to improve the volumetric heat values of the current bio-jet fuels.
Chiral spirodihydroindene skeleton compound and preparation method thereof
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Paragraph 0116-0119; 0121-0122, (2017/02/28)
The invention discloses a chiral spirodihydroindene skeleton compound and a preparation method thereof. The chiral spirodihydroindene skeleton compound is represented by formula I or I'. The preparation method of the chiral spirodihydroindene skeleton compound is characterized in that an intramolecular Friedel-Crafts reaction of a compound represented by formula III is carried out in a solvent under the action of a catalyst to prepare the compound represented by formula I, and the catalyst is a Bronsted acid or a Lewis acid. The preparation method has the advantages of no chiral initial raw material or chiral resolution reagent, no chiral resolution steps, simplicity, simplicity in post-treatment, good economic property, environmental protection, high product yield, and realization of high optical purity and high chemical purity of the product. Transition metal catalyzed asymmetric reaction catalysts prepared by adopting the chiral spirodihydroindene skeleton compound have a substantial catalysis effect, the product yield is greater than 99%, and the ee value of the product higher than 99%.
