10488-95-6Relevant articles and documents
Synthesis of coumarins by Pt-catalyzed hydroarylation of propiolic acids with phenols
Oyamada, Juzo,Kitamura, Tsugio
, p. 6918 - 6925 (2006)
Synthesis of coumarins from phenols and propiolic acids was examined by using a Pt catalyst such as PtCl2/AgOTf, K2PtCl4/AgOTf, and K2PtCl4/AgOAc. Propiolic acid reacted even with less reactive phenols in trifluoroacetic acid to give coumarins and dihydrocoumarins. In the case of substituted propiolic acids, phenylpropiolic acid and 2-octynoic acid, the reactions proceeded selectively to afford coumarins in good to high yields.
One-pot synthesis of β-keto esters and preparation of 3-ketopalmitoyl-CoA
Ko?ak, Urban,Kova?, Andreja,Gobec, Stanislav
, p. 1609 - 1612 (2012)
β-Keto esters were synthesized from acyl chlorides and sodium ethyl acetoacetate in EtOH using a simple one-pot, one-step' method. The deacetylation of α-acetyl β-keto ester to β-keto ester was performed simply, by heating the reaction mixture at reflux for 12 hours, without the addition of additional reagents (e.g., NHl, NH MeOH, or NaOH). One of the β-keto esters prepared using this method was ethyl 3-oxohexadecanoate, a key intermediate in the synthesis of 3-ketopalmitoyl coenzyme A (3-oxohexadecanoyl coenzyme A), a potential substrate of the biologically important enzyme 17β-hydroxysteroid dehydrogenase type 12. Georg Thieme Verlag Stuttgart ? New York.
Simple synthesis of enantiomers of 6-hydroxyalkan-4-olides by stereoselective hydrogenation of methyl 4,6-dioxoalkanoates
Schulz, Stefan
, p. 1239 - 1240 (1999)
A simple method for the synthesis of (S,S)- or (R,R)-6-hydroxyalkan-4-olides, components of the pheromonal secretion of the butterfly Idea leuconoe, in high ee by enantioselective hydrogenation of 4,6-diketo esters with a commercial available Ru-BINAP catalyst is described.
Efficient Synthesis of Functionalized β-Keto Esters and β-Diketones through Regioselective Hydration of Alkynyl Esters and Alkynyl Ketones by Use of a Cationic NHC–AuICatalyst
Tarigopula, Chandrahas,Thota, Ganesh Kumar,Balamurugan, Rengarajan
, p. 5855 - 5861 (2016)
Regioselective hydration of α-alkynyl esters and ketones by using a cationic NHC–AuIcatalyst results in β-keto esters and β-diketones, respectively. Controlled release of water in acetone by aldol self-condensation under the reaction conditions makes acetone as better solvent than 1,4-dioxane/water for the hydration of α-alkynyl esters having sensitive ester moieties.
A novel convenient route to the naturally occurring 3-oxoacyl-L-homoserinelactones and related bacterial autoinducers
Dekhane, Mouloud,Douglas, Kenneth T.,Gilbert, Peter
, p. 1883 - 1884 (1996)
The naturally occurring 3-oxohexanoyl-L-homoserinelactone (1a), a bacterial autoinducer has been prepared in 47% overall yield by condensing stable 3-oxohexanoic acid (2), prepared by hydrolysis from the corresponding ester (3), with L-homoserinelactone using hydroxybenzotriazole (HOBT) and dicyclohexylcarbodiimide (DCC) in non-aqueous media.
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Rathke,Deitch
, p. 2953,2955 (1971)
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Synthetic Scope of Br?nsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate
Rahaman, Mizzanoor,Ali, M. Shahnawaz,Jahan, Khorshada,Hinz, Damon,Belayet, Jawad Bin,Majinski, Ryan,Hossain, M. Mahmun
, p. 6138 - 6147 (2021/05/06)
The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Br?nsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl-methyl ketones produced only aryl-migrated products, whereas other ketones yielded a mixture of products. For diaryl ketones, the identity of two inseparable migrated products was confirmed by two-dimensional NMR spectroscopy.
Screening, synthesis, crystal structure, and molecular basis of 6-amino-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles as novel AKR1C3 inhibitors
Zheng, Xuehua,Jiang, Zan,Li, Xiaolin,Zhang, Chen,Li, Zhe,Wu, Yinuo,Wang, Xinhua,Zhang, Chao,Luo, Hai-bin,Xu, Jun,Wu, Deyan
supporting information, p. 5934 - 5943 (2018/11/23)
AKR1C3 is a promising therapeutic target for castration-resistant prostate cancer. Herein, an evaluation of in-house library discovered substituted pyranopyrazole as a novel scaffold for AKR1C3 inhibitors. Preliminary SAR exploration identified its derivative 19d as the most promising compound with an IC50 of 0.160 μM among the 23 synthesized molecules. Crystal structure studies revealed that the binding mode of the pyranopyrazole scaffold is different from the current inhibitors. Hydroxyl, methoxy and nitro group at the C4-phenyl substituent together anchor the inhibitor to the oxyanion site, while the core of the scaffold dramatically enlarges but partially occupies the SP pockets with abundant hydrogen bond interactions. Strikingly, the inhibitor undergoes a conformational change to fit AKR1C3 and its homologous protein AKR1C1. Our results suggested that conformational changes of the receptor and the inhibitor should both be considered during the rational design of selective AKR1C3 inhibitors. Detailed binding features obtained from molecular dynamics simulations helped to finally elucidate the molecular basis of 6-amino-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles as AKR1C3 inhibitors, which would facilitate the future rational inhibitor design and structural optimization.
