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Volonterio A Bellosta S Bravin F Bellucci MC Bruché L Colombo G Malpezzi L Mazzini S Meille SV Meli M Ramírez De Arellano C Zanda M 《Chemistry (Weinheim an der Bergstrasse, Germany)》2003,9(18):4510-4522
Partially modified retro- (PMR) and retro-inverso (PMRI) psi[NHCH(CF(3))]Gly peptides, a conceptually new class of peptidomimetics, have been synthesized in wide structural diversity and variable length by aza-Michael reaction of enantiomerically pure alpha-amino esters and peptides with enantiomerically and geometrically pure N-4,4,4-trifluorocrotonoyl-oxazolidin-2-ones. The factors underlying the observed moderate to good diastereocontrol have been investigated. The conformations of model PMR-psi[NHCH(CF(3))]Gly tripeptides have been studied in solution by (1)H NMR spectroscopy supported by MD calculations, as well as in the solid-state by X-ray diffraction. Remarkable stability of turn-like conformations, comparable to that of parent malonyl-based retropeptides, was evidenced, as a likely consequence of two main factors: 1) severe torsional restrictions about sp(3) bonds in the [CO-CH(2)-CH(CF(3))-NH-CH(R)-CO] module, which is biased by the stereoelectronically demanding CF(3) group and the R side chain; 2) formation of nine-membered intramolecularly hydrogen-bonded rings, which have been clearly detected both in CHCl(3) solution and in some crystal structures. The former factor seems to be more important, as turn-like conformations were found in the solid-state even in the absence of intramolecular hydrogen bonding. The relative configuration of the -C*H(CF(3))NHC*H(R)- stereogenic centers has a major effect on the stability of the turn-like conformation, which seems to require a syn stereochemistry. X-ray diffraction and ab initio computational studies showed that the [-CH(CF(3))NH-] group can be seen as a sort of hybrid between a peptide bond mimic and a proteolytic transition state analogue, as it combines some of the properties of a peptidyl -CONH- group (low NH basicity, CH(CF(3))-NH-CH backbone angle close to 120 degrees, C-CF(3) bond substantially isopolar with the C=O) with some others of the tetrahedral intermediate [-C(OX)(O(-))NH-] involved in the protease-mediated hydrolysis reaction of a peptide bond (high electron density on the CF(3) group, tetrahedral backbone carbon). 相似文献
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S. Nezu S. Walsh V. Meille M. Yoshida J. B. Lando 《Journal of polymer science. Part A, Polymer chemistry》1995,33(6):973-977
The dimer, trimer, and tetramer of 1,11-dodecadiyne, HC?C? (CH2)8? C?CH, were synthesized. The solid-state polymerization of the dimer was investigated by infrared (IR) spectroscopy. IR bands due to the diacetylene moiety were identified through the comparison of the IR spectra of the dimer, trimer, and tetramer. The dimer was found to have two polymorphs, melt-crystallized and solution-crystallized. Both of the polymorphs undergo solid-state polymerization by exposure to γ-ray or UV irradiation. The former has higher polymerizability for the diacetylene moiety than the latter. The solid-state polymerization of the terminal acetylene group was not observed. It is shown that the previously reported dimer structure in which both the diacetylene and terminal acetylene groups are polymerized to form an inherently electrically conducting polymer is incorrect. © 1995 John Wiley & Sons, Inc. 相似文献
3.
Sergio Auricchio Ada M. Truscello Mirvana Lauria Stefano V. Meille 《Tetrahedron》2012,68(36):7441-7449
2H-Azirines were found to react with imines, enaminones and enaminoesters in the presence of metal salts. Imidazoles, pyrroles and new pyrrolinones derivatives are isolated in good overall yields. The role of metal salts was investigated as they can act as Lewis acids or electron donors. Mechanisms are proposed suggesting that imidazoles arise from addition of azirine to imines via radical or ionic mechanism; pyrroles and pyrrolinones are obtained from azirines with enamino derivatives when the salt acts as a Lewis acid. In the latter case the properties of the metallic compound influence the reaction regioselectivity. 相似文献
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Maurizio Sansotera Cristian Gambarotti Antonino Famulari Alberto Baggioli Raffaella Soave Francesco Venturini Stefano V. Meille Ivan Wlassics Walter Navarrini 《Tetrahedron》2014
Perfluoroalkyl radicals, generated by thermal decomposition of perfluorodiacyl peroxides, react selectively with quinone rings of 1,4-naphthoquinones. In the presence of a non-conjugated alkene such as 1-hexene, perfluoroalkyl radicals add to the double bonds of the olefin forming a radical adduct, which selectively adds to the naphthoquinone ring. Several perfluorodiacyl peroxides have been synthesized and used for the direct and alkene-mediated functionalization of naphthoquinones. Geometrical parameters and electron density topology of all perfluorodiacyl peroxides have been calculated by the density functional formalism and quantum theory of atoms in molecules to attempt a rationalization of the experimental reactivity. 相似文献
5.
The effect of diethylamine (S) in the extraction of nickel and cobalt thenoyl-trifluoroacetonates (MT2) was studied. The results showed that quantitative extraction may be carried out, with formation of a single species MT2S2, which is more stable with cobalt than with nickel. An aqueous solution of these two cations may be analysed by liquid-liquid extraction and gas chromatography of the organic phase.
Zusammenfassung
Der Einfluss von Diäthylamin (S) bei der Extraktion von Nickel- und Kobaltthenoyltrifluoracetonat (MT2) wurde untersucht. Die Ergebnisse zeigten, dass eine quantitative Extraktion unter Bildung einer einzigen Spezies MT2S2 ausgeführt werden kann, wobei die Verbindung mit Kobalt stabiler als die mit Nickel ist. Eine wässrige Lösung dieser beiden Kationen kann durch Flüssig-Flüssig-Extraktion und durch Gaschromatographie der organischen Phase analysiert werden. 相似文献
6.
Abdallah R Meille V Shaw J Wenn D de Bellefon C 《Chemical communications (Cambridge, England)》2004,(4):372-373
A microstructured mesh contactor that can offer residence time of more than minutes is used for gas-liquid-solid hydrogenations and gas-liquid asymmetric hydrogenations. Applications for catalyst/chiral inductor screening and for kinetic data acquisition are demonstrated. 相似文献
7.
Giovanni Ricci Aldo Boglia Tiziano Motta Fabio Bertini Antonella Caterina Boccia Lucia Zetta Enrica Alberti Antonino Famulari Paolo Arosio Stefano Valdo Meille 《Journal of polymer science. Part A, Polymer chemistry》2007,45(22):5339-5353
The (E) isomer in mixtures of (E) and (Z) 1,3‐hexadiene was polymerized with the system CoCl2(PiPrPh2)2‐MAO, a highly active and stereospecific catalyst for the preparation of 1,2 syndiotactic polybutadiene. A new crystalline polymer with a melting point of 109 °C was obtained. The polymer was characterized by IR, NMR (13C, 1H in solution and 13C in the solid‐state), X‐ray diffraction, DSC, GPC and it was found to have a trans‐1,2 syndiotactic structure with a 5.18 ± 0.04 Å fiber periodicity. Since only the (E) isomer was polymerized, at the end of the reaction we were able to separate the (Z) isomer, which was ultimately polymerized with CpTiCl3‐MAO at low temperature, obtaining a low molecular weight, stereoregular polymer that, characterized by IR and NMR methods, was found to exhibit a cis‐1,2 syndiotactic structure, never reported before. Molecular mechanics calculations were carried out on the trans‐1,2 syndiotactic polymer and structural models consistent with the X‐ray diffraction data are proposed. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 5339–5353, 2007 相似文献
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Sergio Brückner Paul J. Phillips Khaled Mezghani Stefano V. Meille 《Macromolecular rapid communications》1997,18(1):1-7
The non-parallel chain structure determined for γ-phase isotactic polypropylene (γ-iPP) is confirmed by Rietveld analysis for highly isotactic high molecular mass iPP crystallized at 200 MPa. The new refinement shows that: (i) stereoregularity or crystallization pressure do not significantly influence the lattice dimensions; (ii) defect inclusion in γ-iPP crystals is unlikely. The α and γ forms have nearly identical bulk internal energy and density, but α-iPP should be normally kinetically favored over γ-iPP which may in turn predominate due to its greater ability to host defects at the crystalline-amorphous interface. 相似文献