3609-53-8Relevant articles and documents
Reaction of naphthalene-2,3-dicarbaldehyde with cyanide; a unique oxidative condensation product
McGill, Colin M.,Swearingen, Kristian E.,Drew, Kelly L.,Rasley, Brian T.,Green, Thomas K.
, p. 475 - 481 (2005)
Naphthalene-2,3-dicarbaldehyde (NDA), a reagent used for the fluorescent detection of amino acids in the presence of cyanide, self-condenses in the presence of cyanide ion and methanol at room temperature to yield a unique crystalline product 2, 15-hydroxybenzo[g]benzo[6,7]isochromeno[4,3-c]isochromen- 7(15H)-one. The product is proposed to result from facile air oxidation of NDA to a methyl ester in combination with benzoin condensation. Product 2 does not to form in the absence of air. The gHMBC spectrum of 2 distinguishes it from a possible alternative isomeric condensation product.
HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls
Niu, Kaikai,Shi, Xiaodi,Ding, Ling,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin
, (2021/12/13)
The construction of C?O bonds through C?H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments.
Visible light-mediated, high-efficiency oxidation of benzyl to acetophenone catalyzed by fluorescein
Geng, Haoxing,Liu, Xin,Zhu, Qing
supporting information, (2021/12/20)
An environmentally friendly aerobic oxidation of benzyl C(sp3)-H bonds to ketones via selective oxidation catalysis was developed. Fluorescein is an efficient photocatalyst with excellent chemical selectivity. The reaction has a wide substrate scope, and a successful gram-scale experiment demonstrated its potential industrial utility.
Carboxyl Methyltransferase Catalysed Formation of Mono- and Dimethyl Esters under Aqueous Conditions: Application in Cascade Biocatalysis
Ashbrook, Chloe,Carnell, Andrew J.,Goulding, Ellie,Hatton, Harry,Johnson, James R.,Kershaw, Neil M.,McCue, Hannah V.,Rigden, Daniel J.,Ward, Lucy C.
supporting information, (2022/02/21)
Carboxyl methyltransferase (CMT) enzymes catalyse the biomethylation of carboxylic acids under aqueous conditions and have potential for use in synthetic enzyme cascades. Herein we report that the enzyme FtpM from Aspergillus fumigatus can methylate a broad range of aromatic mono- and dicarboxylic acids in good to excellent conversions. The enzyme shows high regioselectivity on its natural substrate fumaryl-l-tyrosine, trans, trans-muconic acid and a number of the dicarboxylic acids tested. Dicarboxylic acids are generally better substrates than monocarboxylic acids, although some substituents are able to compensate for the absence of a second acid group. For dicarboxylic acids, the second methylation shows strong pH dependency with an optimum at pH 5.5–6. Potential for application in industrial biotechnology was demonstrated in a cascade for the production of a bioplastics precursor (FDME) from bioderived 5-hydroxymethylfurfural (HMF).
Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis
García Manche?o, Olga,Kuhlmann, Jan H.,Pérez-Aguilar, María Carmen,Piekarski, Dariusz G.,Uygur, Mustafa
supporting information, p. 3392 - 3399 (2021/05/21)
A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.
Novel Bortezomib prodrug and the use thereof
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Paragraph 0088; 0090-0092; 0094-0096, (2021/07/20)
A compound of formula 1 of the invention. The optical isomer or a pharmaceutically acceptable salt thereof is a composition for bone targeting drug delivery by covalently linking a bone directional ligand binding to bone to bortezomib to overcome the tech
Heterocyclic compound as well as preparation method and application thereof
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Paragraph 0120-0125, (2021/02/06)
The invention discloses an immune checkpoint inhibitor heterocyclic compound capable of blocking a VISTA signal path as well as a preparation method and application thereof. The compound is shown as aformula I which is described in the specification. The
METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND
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Paragraph 0053-0056, (2021/03/19)
A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method comprises the following step: (A) providing a compound (I) with an unsaturated double bond, a reagent with trifluoromethyl, and a catalyst; wherein the catalyst is represented by the following formula (II): M(O)mL1yL2z (II); wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and (B) mixing the compound with an unsaturated double bond and the reagent with a trifluoromethyl to perform an oxidation of the compound with the unsaturated double bond by using the catalyst at air or an oxygen condition to get a compound presented as formula (III):
PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation
Wu, Xiaofang,Zhou, Lei,Li, Fangshao,Xiao, Jing
, p. 491 - 497 (2021/01/20)
A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.
Organotellurium-catalyzed oxidative deoximation reactions using visible-light as the precise driving energy
Deng, Xin,Qian, Rongrong,Zhou, Hongwei,Yu, Lei
supporting information, p. 1029 - 1032 (2020/10/23)
Irradiated by visible light, the recyclable (PhTe)2-catalyzed oxidative deoximation reaction could occur under mild conditions. In comparison with the thermo reaction, the method employed reduced catalyst loading (1 mol% vs. 2.5 mol%), but afforded elevated product yields with expanded substrate scope. This work demonstrated that for the organotellurium-catalyzed reactions, visible light might be an even more precise driving energy than heating because it could break the Te–Te bond accurately to generate the active free radical catalytic intermediates without damaging the fragile substituents (e.g., heterocycles) of substrates. The use of O2 instead of explosive H2O2 as oxidant affords safer reaction conditions from the large-scale application viewpoint.
