148-53-8Relevant academic research and scientific papers
Asymmetric Henry reaction catalyzed by a copper tridentate chiral schiff-base complex
Lai, Guoyin,Wang, Sujing,Wang, Zhiyong
, p. 1813 - 1819 (2008)
A series of copper-tridentate chiral Schiff-base complexes were prepared and employed in an asymmetric Henry reaction, affording the corresponding adducts in good yields and with high enantioselectivities (up to 96% ee).
Synthesis, structure and stability of a chiral imine-based Schiff-based ligand derived from L-glutamic acid and its [Cu4] complex
Muche, Simon,Levacheva, Irina,Samsonova, Olga,Biernasiuk, Anna,Malm, Anna,Lonsdale, Richard,Popio?ek, ?ukasz,Bakowsky, Udo,Ho?yńska, Ma?gorzata
, p. 231 - 236 (2017)
Studies of the stability of a ligand derived from L-glutamic acid and ortho-vanillin and its new [Cu4] complex are presented. The [Cu4] complex contains a heterocubane [CuII4O4] core and pendant carboxylic groups increasing its solubility in water, also under basic conditions. The stability of the complex in different solvents is confirmed with ESI-MS studies and such experiments as successful recrystallization. The complex is stable also under physiological conditions whereas the ligand is partly decomposed to L-glutamic acid and ortho-vanillin.
ortho-Hydroxylation of Aromatic Aldehydes: A Short Synthesis of 2-Hydroxypyrene-1-carbaldehyde
Einhorn, Jacques,Luche, Jean-Louis,Demerseman, Pierre
, p. 1350 - 1352 (1988)
A new methodology for the ortho-hydroxylation of aromatic aldehydes via ortho-lithiated aromatic amino alkoxides provides easy access to 2-hydroxypyrene-1-carbaldehyde, a valuable precursor for biologically important pyrenofurans and pyrenocoumarins.
Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship
Alam, Md. Iqbal,Alam, Mohammed A.,Alam, Ozair,Nargotra, Amit,Taneja, Subhash Chandra,Koul, Surrinder
, p. 209 - 219 (2016)
In our earlier study, we have reported that a phenolic compound 2-hydroxy-4-methoxybenzaldehyde from Janakia arayalpatra root extract was active against Viper and Cobra envenomations. Based on the structure of this natural product, libraries of synthetic structurally variant phenolic compounds were studied through molecular docking on the venom protein. To validate the activity of eight selected compounds, we have tested them in in vivo and in vitro models. The compound 21 (2-hydroxy-3-methoxy benzaldehyde), 22 (2-hydroxy-4-methoxybenzaldehyde) and 35 (2-hydroxy-3-methoxybenzylalcohol) were found to be active against venom-induced pathophysiological changes. The compounds 20, 15 and 35 displayed maximum anti-hemorrhagic, anti-lethal and PLA2 inhibitory activity respectively. In terms of SAR, the presence of a formyl group in conjunction with a phenolic group was seen as a significant contributor towards increasing the antivenom activity. The above observations confirmed the anti-venom activity of the phenolic compounds which needs to be further investigated for the development of new anti-snake venom leads.
Iron-catalyzed arene C-H hydroxylation
Cheng, Lu,Wang, Huihui,Cai, Hengrui,Zhang, Jie,Gong, Xu,Han, Wei
, p. 77 - 81 (2021/10/05)
The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.
Enantioselective Hydroboration of Ketones Catalyzed by Rare-Earth-Metal Complexes Supported with Phenoxy-Functionalized TsDPEN Ligands
Yu, Qishun,Lu, Chengrong,Zhao, Bei
supporting information, p. 2529 - 2537 (2021/07/28)
Six novel chiral rare-earth-metal complexes bearing the phenoxy-functionalized TsDPEN ligand H3L1 (H3L1 = N-((1R,2R)-2-((3,5-di-Tert-butyl-2-hydroxybenzyl)amino)-1,2-diphenylethyl)-4-methylbenzenesulfonamide) were synthesized successfully and well characterized. The solid-state structures of four tetranuclear rare-earth-metal complexes [RE2L13]2 (RE = Nd (1), Sm (2), Eu (3), Gd (4)) and the dual-core yttrium complex Y2L13 (5) were determined by X-ray diffraction, respectively. The structure of lanthanum complex 6 was speculated by the 1H DOSY spectroscopy in THF-d8 together with DFT calculations. Complexes 1-5 were employed to catalyze the enantioselective hydroboration of ketones and α,β-unsaturated ketones using pinacolborane (HBpin) as a reductant, and complex 1 gave better outcomes in comparison to the others. The corresponding secondary alcohols were obtained in excellent yields and moderate ee values. The same results were also achieved using the combined catalyst system of the neodymium amide Nd[N(SiMe3)2]3 with the phenoxy-functionalized TsDPEN ligand H3L1 in a 1:1.5 molar ratio.
Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles
Huang, You,Li, Xiaohu
supporting information, p. 9934 - 9937 (2021/10/12)
A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.
Solvent-free, microwave assisted oxidation of alcohols with 4-hydroxypyridinium chlorochromate functionalized silica gel
AHMADI, Sayed Ali,GHALEHBANDI, Shermineh Sadat,GHAZANFARI, Dadkhoda,SHEIKHHOSSEINI, Enayatollah
, p. 283 - 289 (2020/10/06)
4-Hydroxypyridinium chlorochromate functionalized silica gel was found to be an efficient and reusable oxidant for the very fast oxidation of primary and secondary alcohols to the corresponding carbonyl compounds under solventfree conditions and microwave irradiation in excellent yields.
Method for preparing aldehyde compounds through photocatalytic oxidation cracking β - hydroxyl compound C-C bond
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Paragraph 0078-0079, (2020/07/29)
The invention provides a method for preparing aldehydes from C-C bonds of beta-hydroxy compounds by photocatalytic oxidative cracking. According to the method, the beta-hydroxy compounds are taken asa substrate, oxygen-containing gas is taken as an oxygen source, and C-C bond cracked products, namely, corresponding aldehydes can be generated under illumination in presence of a catalyst. The conditions are mild, the oxidation efficiency and the product yield are high, and the oxygen-containing gas is taken as the oxygen source under the illumination condition, so that the method is economical,environmentally friendly and green, meets the strategy of sustainable developed energy and has broad application prospect.
The invention relates to a catechol is raw material of synthetic small bo hong alkali method (by machine translation)
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, (2019/05/15)
The invention relates to a catechol is raw material of synthetic small bo hong alkali method, relates to a method for drug synthesis, in order to catechol as raw materials, with the catechol 2 - methyl chloride selective methylation reaction get O-methoxyphenol, continue to selective hydroformylation reaction to obtain the 2 - hydroxy - 3 - methoxybenzaldehyde; with the catechol 2 - methyl chloride methylene compounds obtained by reaction of pepper link, to continue to work with 2 - chloroethylamine catalytic addition reaction pepper ethylamine; the pepper ethylamine with 2 - hydroxy - 3 - methoxybenzaldehyde in a nickel-based catalyst "one-pot" condensation under the conditions of the hydrogenation reaction, the reaction product is hydrochloric acid, cooling of the crystal, and filtering to obtain the hydrochloride condensate; will be hydrochloride compression compound refined, continue to work with the glyoxal, under the condition of a copper-based catalyst, a cyclization reaction is carried out, the reaction product after passing through the refining process, hydrochloric acid, cooling crystallization, filtration washing to obtain the product of the ABS red alkali. The industrialization of this invention fully synthetic production of the ABS red alkali, to create a small bo hong alkali drug chemical synthesis method. (by machine translation)
