119-52-8Relevant articles and documents
Reduction of 1,2-diketones with titanium tetraiodide: A simple approach to α-hydroxy ketones
Hayakawa,Sahara,Shimizu
, p. 7939 - 7942 (2000)
1,2-Diketones are readily reduced with titanium tetraiodide to give α-hydroxy ketones in good to excellent yields. Regioselectivity on the reduction of unsymmetrical substrates is also discussed. (C) 2000 Elsevier Science Ltd.
Study on the reactivity of aldehydes in electrolyzed ionic liquids: Benzoin condensation - Volatile organic compounds (VOCs) vs. room temperature ionic liquids (RTILs)
Chiarotto,Feroci,Orsini,Feeney,Inesi
, p. 3287 - 3292 (2010)
The benzoin condensation of aromatic and heteroaromatic aldehydes, catalyzed by electrochemically generated N-heterocyclic carbenes, has been set up in the absence of organic solvents and bases. α-Hydroxy ketones have been isolated in good to elevated yields, in short reaction times. Aldol products and carbene-aldehyde adducts have been obtained in elevated yields from linear and short branched aldehydes, respectively. A comparison with the use of classical organic solvents has been reported Copyright
Synthesis of pentafluorobenzene-based NHC adducts and their catalytic activity in the microwave-assisted reactions of aldehydes
Papadaki, Evanthia,Magrioti, Victoria
, (2020)
N-Heterocyclic carbenes (NHCs) have been widely used in organometallic chemistry as ligands, as well as standalone organocatalysts in various reactions, mostly using aromatic aldehydes as substrates. We have previously demonstrated the efficiency of azolium-2-carboxylate zwitterions in the hydroxymethylation of aldehydes, especially aliphatic aldehydes, under microwave irradiation. In the present work, we report a series of pentafluorobenzene-based NHC adducts and their efficiency in the hydroxymethylation and self-condensation of aliphatic and aromatic aldehydes using microwave irradiation. The free carbenes are released under the reaction conditions and 1,3-dimesityl-2-(perfluorophenyl)imidazolidine and 1,3-bis(2,6-dimethylphenyl)-2-(perfluorophenyl)imidazolidine proved to be the most potent precatalysts.
One-step assembly of functionalized γ-butyrolactones from benzoins or benzaldehydes via an N-heterocyclic carbene-mediated tandem reaction
Ye, Wei,Cai, Guanliang,Zhuang, Zeyang,Jia, Xueshun,Zhai, Hongbin
, p. 3769 - 3771 (2005)
(Chemical Equation Presented) We describe here a direct, efficient, one-step construction of γ,γ-difunctionalized γ-butyrolactones from benzoins or benzaldehydes via a tandem reaction promoted by 1,3-dimethyl imidazolin-2-ylidene, an N-heterocyclic carbene (NHC).
An efficient nucleophilic carbene catalyst for the asymmetric benzoin condensation
Enders, Dieter,Kallfass, Ulrike
, p. 1743 - 1745 (2002)
The chiral bicyclic triazolium salt 1 is currently the most efficient precatalyst for the asymmetric benzoin condensation. The substituted acyloins 3 are obtained in moderate to good yields and with very good enantiomeric excesses from the corresponding aldehydes 2. The high asymmetric induction is presumably based on the conformational rigidity of the bicyclic nucleophilic carbene catalyst and on the steric hindrance of the tert-butyl group in the Breslow intermediate.
Wash-free 3D imaging and detection of glioma with a novel neuropotential targeted AIE probe
Wu, Junyong,Bi, Anyao,Zheng, Fan,Huang, Shuai,Li, Yongjiang,Ding, Jipeng,Xiang, Daxiong,Zeng, Wenbin
, p. 801 - 804 (2021)
We herein developed a novel tetraarylimidazole-based AIE probe TPIG-NP to selectively image and quantitatively detect glioma. Due to the distinct negatively charged glioma cells, TPIG-NP with an opposite charge could achieve wash-free imaging of glioma cells and 3D multicellular spheroids. This journal is
Asymmetric benzoin condensation promoted by chiral triazolium precatalyst bearing a pyridine moiety
Soeta, Takahiro,Tabatake, Yuhta,Inomata, Katsuhiko,Ukaji, Yutaka
, p. 894 - 899 (2012)
Chiral triazolium salts bearing a pyridine ring were developed as N-heterocyclic carbene precursors. In the presence of the chiral triazolium salt and a base, the catalytic asymmetric benzoin condensation proceeded to afford the product in high level of chemical yield and enantioselectivity. A wide range of aromatic aldehydes were applicable to this reaction.
Versatile access to benzhydryl-phenylureas through an unexpected rearrangement during microwave-enhanced synthesis of hydantoins
Muccioli, Giulio G.,Wouters, Johan,Poupaert, Jacques H.,Norberg, Bernadette,Poppitz, Wolfgang,Scriba, Gerhard K. E.,Lambert, Didier M.
, p. 3599 - 3602 (2003)
(Equation presented) A new access to benzhydryl-phenylureas is described. These new interesting urea derivatives were obtained by reaction of substituted benzils with substituted phenylureas under microwave irradiation. Phenylthiourea, when reacted with benzil, gave 3-phenyl-thiohydantoin. Moreover, benzylurea, as phenethylurea, gave the corresponding 3-substituted hydantoin derivatives, demonstrating that only phenylurea derivatives can result in benzhydryl-phenylureas under the applied conditions. This new reaction proved to be an easy access to substituted 1-benzhydryl-3-phenyl-ureas.
Asymmetric benzoin reaction catalyzed by benzoylformate decarboxylase
Demir, Ayhan S.,Duennwald, Thomas,Iding, Hans,Pohl, Martina,Mueller, Michael
, p. 4769 - 4774 (1999)
Aromatic aldehydes are converted into benzoins by benzoylformate decarboxylase catalyzed C-C bond formation. The reaction affords (R)-benzoins with high enantiomeric excess and in good chemical yields. A broad range of aromatic aldehydes can be used as substrates in aqueous buffer or buffer/DMSO-solutions. (C) 2000 Elsevier Science Ltd.
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Will,Rhodius
, p. 230 (1848)
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Unexpected transformation of aldehydes into benzoins with Copper(I)/Samarium
Liu, Yongjun,Wang, Hui,Fu, Yulong,Qi, Yan,Yang, Kuiwei
, p. 259 - 266 (2014)
The reductive coupling of aldehydes to afford pinacolic alcohols using all kinds of reducing agents involving samarium is well known. In this report, however, treatment of aromatic aldehydes with Cu(I)/Sm system produces benoins and/or benzils in good yields. A possible mechanism is proposed where Cu(I) not only activates the Sm metal but also promotes the dehydrogenation of the intermediates, during which a Cu(III) species may be involved. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
NaBrO3/bmim[HSO4]: a versatile system for the selective oxidation of 1,2-diols, α-hydroxyketones, and alcohols
Khurana, Jitender M.,Lumb, Anshika,Chaudhary, Ankita
, p. 381 - 386 (2017)
Abstract: Sodium bromate with bmim[HSO4] has been found to be an excellent oxidizing agent in aqueous medium. NaBrO3:bmim[HSO4] oxidized 1,2-diols, α-hydroxyketones, and alcohols to the corresponding carbonyl compounds in excellent yields. This method offers advantages such as low cost reagents, aqueous reaction conditions, moderate temperatures and short reaction times and hence environmentally benign reaction. Moreover, the ionic liquid bmim[HSO4] could be recycled for at least three times without loss of significant activity. Graphical abstract: [Figure not available: see fulltext.]
Enzyme catalyzed hydroxymethylation of aromatic aldehydes with formaldehyde. Synthesis of hydroxyacetophenones and (S)-benzoins
Demir, Ayhan S.,Ayhan, Peruze,Igdir, A. Cigdem,Duygu, A. Nese
, p. 6509 - 6512 (2004)
Benzaldehyde lyase from the Pseudomonas Fluorescens catalyzed reaction of aromatic aldehydes with formaldehyde providing 2-hydroxy-1-arylethan-1-one in high yields via an acyloin linkage. Kinetic resolution of rac-benzoins with formaldehyde providing (S)-benzoins and 2-hydroxy-1-arylethan-1-one via C-C bond cleavage and a bond formation reaction.
A reductase-mimicking thiourea organocatalyst incorporating a covalently bound NADH analogue: Efficient 1,2-diketone reduction with in situ prosthetic group generation and recycling
Procuranti, Barbara,Connon, Stephen J.
, p. 1421 - 1423 (2007)
A new class of bifunctional organocatalyst promotes the chemoselective reduction of diketone electrophiles at catalytic loadings in the presence of an inorganic co-reductant. The Royal Society of Chemistry.
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Sumrell et al.
, p. 39 (1957)
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Revealing aggregation-induced emission effect of imidazolium derivatives and application for detection of Hg2+
Huang, Shuai,Gao, Tang,Bi, Anyao,Cao, Xiaozheng,Feng, Bin,Liu, Min,Du, Tao,Feng, Xueping,Zeng, Wenbin
, (2020)
Despite being highly emissive in solution, aggregation of 4-(4,5-bis(4-methoxyphenyl)-1H- imidazole-2-yl) benzaldehyde (BMI) molecules typically results in the quenching of fluorescence. To overcome the shortcomings of aggregation-caused quenching (ACQ), the substituent of imidazole in the nitrogen atom of the BMI have been found as a conformation function group (CFG) to turn the aggregation-induced emission (AIE) effect. The introduction of CFG not only causes the restriction of intramolecular rotations (RIR) effect, but also attenuates the coplanarity of the molecule. As a result, the BMI with ACQ effect is transformed into BMIs with AIE effect. As the steric hindrance of the CFG increases, the AIE characteristic of the derivative also becomes apparent. With the assistance of the thioacetal unit, BMIBD can act as an outstanding probe for the detection of Hg2+ with high sensitivity and selectivity. A series of characterizations were implemented to prove the unique response mechanism of BMIBD toward mercury ions, including optical behavior investigation, mass analysis and 1H NMR studies. Further, the detection limit is low up to 36 nM. Taking advantages of excellent optical properties of this AIE probe BMIBD, point-of-care testing (POCT) for Hg2+ detection was further investigated. Meanwhile, BMIBD presented the desirable analytical property for the real water samples. Additionally, cellular imaging experiment revealed that the probe has an excellent biocompatibility that could be applied for tracking Hg2+ in living cells.
Structure-based design, synthesis, molecular docking study and biological evaluation of 1,2,4-triazine derivatives acting as COX/15-LOX inhibitors with anti-oxidant activities
Khoshneviszadeh, Mehdi,Shahraki, Omolbanin,Khoshneviszadeh, Mahsima,Foroumadi, Alireza,Firuzi, Omidreza,Edraki, Najmeh,Nadri, Hamid,Moradi, Alireza,Shafiee, Abbas,Miri, Ramin
, p. 1602 - 1611 (2016)
A set of 1,2,4-triazine derivatives were designed as cyclooxygenase-2 (COX-2) inhibitors. These compounds were synthesized and screened for inhibition of cyclooxygenases (COX-1 and COX-2) based on a cellular assay using human whole blood (HWB) and lipoxygenase (LOX-15) that are key enzymes in in?ammation. The results showed that 3-(2-(benzo[d][1,3]dioxol-5-ylmethylene)hydrazinyl)-5,6-bis(4-methoxyphenyl)-1,2,4-triazine (G11) was identified as the most potent COX-2 inhibitor (78%) relative to COX-1 (50%). Ferric reducing anti-oxidant power (FRAP) assay revealed that compound G10 possesses the highest anti-oxidant activity. The compound G3 with IC50 value of 124 μM was the most potent compound in LOX inhibitory assay. Molecular docking was performed and a good agreement was observed between computational and experimental results.
Benzoin reaction in water as an aqueous medium catalyzed by benzimidazolium salt
Iwamoto, Ken-ichi,Hamaya, Masako,Hashimoto, Naoki,Kimura, Hitomi,Suzuki, Yumiko,Sato, Masayuki
, p. 7175 - 7177 (2006)
Benzoin reactions are catalyzed by N,N-dialkylbenzimidazole to yield α-hydroxy ketones; the reaction proceeds in water as an aqueous medium under mild conditions. The utility of these salts as pre-catalysts in these reactions has been demonstrated.
Enantioselective Acyloin Rearrangement of Acyclic Aldehydes Catalyzed by Chiral Oxazaborolidinium Ion
Cho, Soo Min,Lee, Si Yeon,Ryu, Do Hyun
supporting information, p. 1516 - 1520 (2021/03/03)
A catalytic enantioselective acyloin rearrangement of acyclic aldehydes to synthesize highly optically active acyloin derivatives is described. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction provided chiral α-hydroxy aryl ketones in high yield (up to 95%) and enantioselectivity (up to 98% ee). In addition, the enantioselective acyloin rearrangement of α,α-dialkyl-α-siloxy aldehydes produced chiral α-siloxy alkyl ketones in high yield (up to 92%) with good enantioselectivity (up to 89% ee).
Application of N-heterocyclic carbene selenium-gold compound in preparation of carbapenem-resistant acinetobacter baumannii drug
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Paragraph 0024; 0029-0032; 0038, (2021/07/21)
The invention discloses application of an N-heterocyclic carbene selenium-gold compound in preparation of a novel antibacterial drug resistant to carbapenem acinetobacter baumannii infection, and belongs to the technical field of drug preparation. According to the N-heterocyclic carbene selenium-gold compound, selenium-containing imidazole N-heterocyclic carbene selenium is used for replacing a thiosaccharide ligand in a gold nofen structure; the reaction activity of Au-Se in the N-heterocyclic carbene selenium-gold compound is higher than that of an Au-S bond, so that the Au-S bond in a Jinnofen structure can be prevented from being easily damaged by reducing mercaptan to a certain extent; and toxic and side effects are caused by metabolism before reaching a target spot. In-vitro antibacterial activity shows that IC50 of the compounds H7 and H8 in inhibition of carbapenem-resistant acinetobacter baumannii is 3.34 mu M and 4.67 mu M, MIC of the same are both 10 mu M, and MBC of the same are both 20 mu M. The animal in-vivo administration also shows a good anti-drug-resistant bacterium effect, which proves that the compound can significantly prolong the survival time of mice infected by drug-resistant bacteria, and has important practical application value.
