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N,S-缩烯酮是一类重要的有机合成中间体,其官能团的多样性决定了反应的多样性。N,S-缩烯酮的主要反应有与亲核体的共轭加成、与金属有机试剂的选择性加成、环合(五元环或六元环)、还原和缩合等反应,其在杂环合成中具有非常重要的意义。本文主要综述了N,S-缩烯酮的制备及其在参与合成含氮杂环(吡咯、吲哚、吡啶、嘧啶等)、含氧杂环(呋喃、吡喃等)及在多组分反应中的应用,重点介绍了各类反应的普适性、反应机理或衍生化的研究结果,以更好地认识N,S-缩烯酮分子,并期望通过N,S-缩烯酮实现选择性的合成各类所需的杂环化合物,以促进N,S-缩烯酮在杂环合成中的应用。此外,N,S-缩烯酮合成的杂环化合物大部分具有潜在的生物活性,这将促进其在药物化学及药物合成领域的应用和发展。 相似文献
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A dicyclopropyl ketimine may be formed by the addition of cyclopropyllithium to 1-cyano-1-piperidinocyclopropane. Rearrangement of the ketimine takes place under acid catalysis to form 1-pyrrolizidinone. 相似文献
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Asymmetric syntheses of (S)-α-amino acids in 28--98% optical yields via doublechiral induction in alkylations of ketimine 1 derived from (+)-2-hydroxypinan-3-one and (-)-men-thyl glycinate which is a chiral match pair have been studied. The factors controlling the diastereoselec-tivities in alkylation reactions of the ketimine, the properties of alkylating agents and various alkylationconditions are examined. 相似文献
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2‐Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis 下载免费PDF全文
Manuel Iniesta Dr. Ana Martín‐Somer Mario Parra Prof. Dr. Sergio Díaz‐Tendero Prof. Dr. Alberto Fraile Prof. Dr. Jose Alemán 《Angewandte Chemie (International ed. in English)》2018,57(19):5350-5354
An organocatalytic system is presented for the Michael addition of monoactivated glycine ketimine ylides with a bifunctional catalyst. The ketimine bears an ortho hydroxy group, which increases the acidity of the methylene hydrogen atoms and enhances the reactivity, thus allowing the synthesis of a large variety of α,γ‐diamino acid derivatives with excellent stereoselectivity. 相似文献
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James L. Hedrick W. Volksen Dillip K. Mohanty 《Journal of polymer science. Part A, Polymer chemistry》1992,30(10):2085-2097
Imide-aryl ether ketone block copolymers were prepared and their morphology and thermal and mechanical properties investigated. Two aryl ether ketone blocks were incorporated; the first was an amorphous block derived from bisphenol–A and the second block was a semi-crystalline poly(aryl ether ether ketone) prepared from a soluble and amorphous ketimine precursor. Bis(amino) aryl ether ketone and aryl ether ketimine oligomers were prepared via a nucleophilic aromaic substitution reaction with molecular weights ranging from 6,000 to 12,000 g/mol. The oligomers were co-reacted with 4,4′-oxydianiline (ODA) and pyromellitic dianhydride (PMDA) diethyl ester diacyl chloride in N-methyl–2-pyrrolidone (NMP) in the presence of N-methylmorpholine. The copolymer compositions, determined by H-NMR, of the resulting amic ester based copolymers ranged from 8 to 50 wt % aryl ether ketone or ketimine content. Prior to imide formation, the ketimine moiety of the aryl ether ketimine block was hydrolyzed (p-toluene sulfonic acid) to the ketone form producing the aryl ether ether ketone block. Compositions of this block were maintained low to retain solubility. Solutions of the copolymers were cast and cured to effect imidization, producing clear films with high moduli (ca. 2200 MPa) and elongations (33–100%). The copolymers displayed good thermal stability with decomposition temperatures in excess of 450°C. Multiphase morphologies were observed irrespective of the co-block type, block length or composition. © 1992 John Wiley & Sons, Inc. 相似文献
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Several imine species comprising N-sulfinyl and N-sulfonyl ketimine, oxime, and enamine derivatives were subjected to asymmetric transfer hydrogenation in an azeotropic mixture of formic acid/triethylamine. Among them, the Rh-catalyzed transfer hydrogenation of N-sulfonyl ketimine afforded the corresponding 1-arylalkylamines in excellent yield and with high enantioselectivity. 相似文献
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Olli Martiskainen Ryszard Gawinecki Borys Ośmiałowski Kirsti Wiinamäki Kalevi Pihlaja 《Rapid communications in mass spectrometry : RCM》2009,23(7):1075-1084
Tautomerism has been studied conventionally in solutions or in the solid state. However, the importance of mass spectrometry in the gas phase was realized relatively late. 2‐Phenacylquinolines are known to undergo ketimine‐enaminone tautomerism. The ratio of tautomers is dependent on the nature of the phenyl ring substituent and the Hammett substituent constants σ. Theoretical calculations indicate the presence of ketimine and enaminone tautomers in the gas phase. The electron ionization mass spectra of eight 2‐phenacylquinolines (ketimine form) were recorded at 70 eV in order to determine the fragmentation routes and to screen for the presence of their enaminone tautomers, (Z)‐2‐benzoylmethylene‐1,2‐dihydroquinolines, in the gas phase. The relative abundances or total ion currents of some ions correlated with the Hammett substituent constants and Hammett‐Brown constants. The product ions [M–CO]+ . and [M–HCO]+ were observed. A reaction mechanism is suggested for the formation of these ions, requiring skeletal rearrangements. The results furnish information relating to tautomerism in the gas phase. Copyright © 2009 John Wiley & Sons, Ltd. 相似文献
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Density functional theory (DFT) calculations were performed to investigate the mechanism and the enantioselectivity of the aza-Henry reaction of isatin-derived ketimine catalyzed by chiral guanidine–amide catalysts at the M06-2X-D3/6-311+G(d,p)//M06-2X-D3/6-31G(d,p) (toluene, SMD) theoretical level. The catalytic reaction occurred via a three-step mechanism: (i) the deprotonation of nitromethane by a chiral guanidine–amide catalyst; (ii) formation of C–C bonds; (iii) H-transfer from guanidine to ketimine, accompanied with the regeneration of the catalyst. A dual activation model was proposed, in which the protonated guanidine activated the nitronate, and the amide moiety simultaneously interacted with the ketimine substrate by intermolecular hydrogen bonding. The repulsion of CPh3 group in guanidine as well as N-Boc group in ketimine raised the Pauli repulsion energy (∆EPauli) and the strain energy (∆Estrain) of reacting species in the unfavorable si-face pathway, contributing to a high level of stereoselectivity. A new catalyst with cyclopropenimine and 1,2-diphenylethylcarbamoyl as well as sulfonamide substituent was designed. The strong basicity of cyclopropenimine moiety accelerated the activation of CH3NO2 by decreasing the energy barrier in the deprotonation step. The repulsion between the N-Boc group in ketimine and cyclohexyl group as well as chiral backbone in the new catalyst raised the energy barrier in C–C bond formation along the si-face attack pathway, leading to the formation of R-configuration product. A possible synthetic route for the new catalyst is also suggested. 相似文献
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A convenient synthesis of 5-aryl-1-phenylpyrazoles and 5-arylisoxazoles, from readily available ketimine 1 dimethylformamide dimethylacetal and phenylhydrazine or hydroxylamine, is described. 相似文献
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Ahmad F. Taj M. B. Tirmizi S. A. Alelwani W. Hajjar D. Makki A. A. Shah S. Ali U. Hassan U. Tahir M. Siddiq S. 《Russian Journal of General Chemistry》2019,89(1):142-147
Russian Journal of General Chemistry - The hydrazone derived ketimine of dehydroacetic acid and its metal {Cu(II), Ni(II), Zn(II), Fe(III), Cd(II), Pd(II), La(III), Nd(III), Ce(III)} complexes are... 相似文献
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Versatile and mild: The first general method for the title transformation has been developed (see scheme; 2-F-Py=2-fluoropyridine; Tf=trifluorosulfonyl). The amines are synthesized in good yields and the ketimine intermediates can be isolated before the reduction. This method should find applications in the synthesis of nitrogen-containing bioactive molecules and medicinal agents. 相似文献