698-27-1Relevant academic research and scientific papers
Synthesis and spectra characteristics of novel 3-(para-Bromophenyl)-7- (substituted vinyl) coumarins
Wang, Lingyun,Zou, Hanxun,Ye, Decheng,Cao, Derong
, p. 551 - 556 (2013)
Five new coumarin derivatives (5a-5e) with extending para-bromophenyl at the 3-position and substituted vinyl at the 7-position were synthesized and characterized by FT-IR, 1H NMR, and element analysis. The absorption and fluorescence character
Total synthesis of the proposed structure of Anti-TMV active tabasesquiterpene A
Kumari, Anusueya,Suresh, Muthiah,Singh, Raj Bahadur
, (2021/06/17)
The proposed structure of Tabasesquiterpene A, an illudalane type of sesquiterpene has been synthesized in twelve steps from 2-methoxy-4-methylbenzaldehyde in 40% overall yield. Triflic acid mediated intramolecular Freidel-Crafts acylation allows to develop the critical indanone moiety, a key intermediate of this synthesis. A careful ortho-selective formylation and subsequent Knoevenagel condensation to incorporate three carbon side chain, followed by reduction, formation of tricyclic lactone and DIBAL-H supported reduction of lactone to target were other key transformation involved. The NMR spectroscopic data of the synthetic sample differ from those of natural tabasesquiterpene A.
NOVEL SIRT 1 ACTIVATOR AND MEDICINAL USE THEREOF
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Paragraph 0043-0045, (2020/03/13)
The present invention relates to a SIRT 1 activator and medical use thereof and in the present invention, a novel SIRT 1 activator compound based on benzo[d]furan or a benzo[d]oxazole backbone, a crystalline form thereof, a hydrate thereof, or a salt thereof was prepared, and that the compound has obesity, insulin resistance and dyslipidemia improvement effect, fatty liver improvement effect, cell aging protection, oxidative stress protection and yeast life extension effect, collagen synthesis and wrinkle improvement effect, was confirmed. Therefore, the novel SIRT 1 activator compound having the above-mentioned effect is usefully used as a pharmaceutical composition for preventing or treating metabolic diseases including obesity, diabetes, dyslipidemia, etc., or liver diseases including alcoholic or non-alcoholic fatty liver, fatty hepatitis, etc., a cosmetic composition for preventing or improving wrinkles, a health food composition for improving cell aging or extending lifespan, and the like.
Phosphine-Catalyzed [3+2] Annulation of β-Sulfonamido-Substituted Enones with Sulfamate-Derived Cyclic Imines
Shi, Wangyu,Zhou, Leijie,Mao, Biming,Wang, Qijun,Wang, Chang,Zhang, Cheng,Li, Xuefeng,Xiao, Yumei,Guo, Hongchao
supporting information, p. 679 - 685 (2019/01/24)
Phosphine-catalyzed [3+2] annulation of β-sulfonamido-substituted enones and sulfamate-derived cyclic imines has been developed, giving a series of imidazoline derivatives in moderate to excellent yields with good to excellent diastereoselectivities. A scale-up reaction worked well under mild reaction conditions. A possible mechanism was proposed on the basis of the results obtained.
Directed Hydroxylation of sp2 and sp3 C-H Bonds Using Stoichiometric Amounts of Cu and H2O2
Trammell, Rachel,D'Amore, Lorenzo,Cordova, Alexandra,Polunin, Pavel,Xie, Nan,Siegler, Maxime A.,Belanzoni, Paola,Swart, Marcel,Garcia-Bosch, Isaac
supporting information, p. 7584 - 7592 (2019/06/11)
The use of copper for C-H bond functionalization, compared to other metals, is relatively unexplored. Herein, we report a synthetic protocol for the regioselective hydroxylation of sp2 and sp3 C-H bonds using a directing group, stoichiometric amounts of Cu and H2O2. A wide array of aromatic ketones and aldehydes are oxidized in the carbonyl γ-position with remarkable yields. We also expanded this methodology to hydroxylate the β-position of alkylic ketones. Spectroscopic characterization, kinetics, and density functional theory calculations point toward the involvement of a mononuclear LCuII(OOH) species, which oxidizes the aromatic sp2 C-H bonds via a concerted heterolytic O-O bond cleavage with concomitant electrophilic attack on the arene system.
MgBr2 supported on Fe3O4@SiO2?~?urea nanoparticle: An efficient catalyst for ortho-formylation of phenols and oxidation of benzylic alcohols
Soleimani, Ebrahim,Yaesoobi, Nadieh,Ghasempour, Hamid Reza
, (2017/10/07)
Urea was successfully immobilized on the surface of chloropropyl-modified Fe3O4@SiO2 core–shell magnetic nanoparticles, then supported by MgBr2 and acts as a unique catalyst for oxidation of benzylic alcohols to aldehydes and ketones, and ortho-formylation of phenols to salicylaldehydes. The prepared catalyst was characterized by FT-IR, transmission electron microscopy, scanning electron microscopy, X-ray powder diffraction, dispersive X-ray spectroscopy, CHN and TGA. It was found that Fe3O4@SiO2?~?urea/MgBr2 showed higher catalytic activity than homogenous MgBr2, and could be reused several times without significant loss of activity.
Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity
Sahani, Rajkumar Lalji,Patil, Manoj D.,Wagh, Sachin Bhausaheb,Liu, Rai-Shung
supporting information, p. 14878 - 14882 (2018/10/15)
The catalytic formation of gold enolates from alkynes, nitrones, and nucleophiles is described, and their Mannich reactions result in nucleophile-directed chemoselectivity through cooperative catalysis. For 1-alkyn-4-ols and 2-ethynylphenols, their gold-catalyzed nitrone oxidations afforded N-containing dihydrofuran-3(2H)-ones with syn selectivity. The mechanism involves the Mannich reactions of gold enolates with imines through an O-H-N hydrogen-bonding motif. For aryloxyethynes, their gold enolates react selectively with nitrones to deliver 3-alkylidenebenzofuran-2-ones, as controlled by a C-H-O hydrogen-bonding motif.
Efficient microwave-assisted regioselective one pot direct: Ortho -formylation of phenol derivatives in the presence of nanocrystalline MgO as a solid base catalyst under solvent-free conditions
Naeimi, Hossein,Zakerzadeh, Elham
, p. 4590 - 4595 (2018/03/21)
In this research, at first nanocrystalline MgO was prepared and then the solvent-free reactions of phenol derivatives with paraformaldehyde in the presence of the obtained nanocrystalline MgO as a new catalyst under microwave irradiation were investigated. In this reaction, ortho-hydroxyaromatic aldehydes were yielded as products. This method seems to be comparable with other reported methods due to its high yield and regioselectivity. The significant features of this method are short reaction times, high yields, and easy and quick isolation of the products.
Enantioselective Construction of Tetrahydroquinazoline Motifs via Palladium-Catalyzed [4 + 2] Cycloaddition of Vinyl Benzoxazinones with Sulfamate-Derived Cyclic Imines
Wang, Chang,Li, Yan,Wu, Yang,Wang, Qijun,Shi, Wangyu,Yuan, Chunhao,Zhou, Leijie,Xiao, Yumei,Guo, Hongchao
supporting information, p. 2880 - 2883 (2018/05/29)
A palladium-catalyzed enantioselective [4 + 2] cycloaddition reaction of vinyl benzoxazinones with sulfamate-derived cyclic imines is described, affording the tetrahydroquinazolines bearing several functional rings in high yields (up to 99% yield) with good to excellent diastereoselectivities and excellent enantioselectivities (up to 96% ee). This reaction represents the first Pd-catalyzed asymmetric decarboxylative cycloaddition of vinyl benzoxazinones with imines.
Efficient synthesis of chiral benzofuryl β-amino alcohols via a catalytic asymmetric Henry reaction
Chen, Wei,Zhou, Zhao-Hui,Chen, Hong-Bin
supporting information, p. 1530 - 1536 (2017/02/15)
Chiral β-amino alcohol ligands were found effective for the copper(ii)-catalyzed asymmetric Henry reaction of benzofuran-2-carbaldehydes with nitromethane, which led to the formation of (S)-enriched benzofuryl β-nitro alcohols with satisfactory enantioselectivities (up to 98% ee). Using this catalytic protocol, bioactive (S)-benzofuryl β-amino alcohols could be conveniently prepared in short steps.
