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1.
The variable temperature (1)H, (13)C, and (19)F NMR spectra were measured for the title N-nitrosamines. The observed unusually low N-N rotation barriers (12-15 kcal/mol) result from a significant deviation of the nitrosamino system from planarity. A pyramidal character of the amino nitrogen was confirmed by the X-ray crystal structures of two compounds and by bathochromic shifts of the n-pi absorption bands in the UV spectra. The nonplanarity of the nitrosamino moiety is due to the strong pseudoallylic A((1,3)) strain caused by the steric interaction of the NNO group with the neighboring aryl substituents fixed in the equatorial positions of the bicyclic skeleton. In addition, the barriers to the C-C rotation of aryl groups were examined at temperatures lower than required to "freeze" the N-N rotation and different DeltaG() values were observed for the aryls oriented syn and anti to the nitroso oxygen. 相似文献
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N-Benzyl-3-thia-9-aza-bicyclo[3.3.1]nonan-7-one has been prepared from methyl 4-bromocrotonate by reaction sequence involving sodium sulfide, benzylamine, and Dieckmann condensation. Some spectral and chemical properties of this system are also reported. 相似文献
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Russian Journal of Organic Chemistry - 相似文献
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《Journal of Coordination Chemistry》2012,65(23):3853-3863
New bidentate Schiff-base ligands 2-(2,4-di-p-tolyl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazinecarbothioamide HL1 and 2-(2,4-di-p-tolyl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazinecarboxamide HL2 were synthesized from the condensation of 2,4-di-p-tolyl-3-azabicyclo[3.3.1]nonan-9-one with thiosemicarbazide and semicarbazide, respectively. Homoleptic complexes of these ligands, of general formula K[Cr(L n )2Cl2], K2[Mn(L n )2Cl2], K2[Fe(L1)2Cl2] and [M(L n )2] (where M = Co(II), Ni(II) Cu(II), Zn(II), Cd(II), and Hg(II) ions; n = 1 or 2) are reported. The mode of bonding and overall geometry of the complexes were determined through IR, UV-Vis, NMR and mass spectral studies, magnetic moment measurements, elemental analysis, metal content, and conductance. These studies revealed octahedral geometry for Cr(III), Mn(II), and Fe(II) complexes, square planar for Cu(II), Co(II), and Ni(II) complexes and tetrahedral for Zn(II), Cd(II), and Hg(II) complexes. 相似文献
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Russian Journal of Organic Chemistry - 相似文献
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The double Michael addition of benzylamine to 3-alkyl-2,7-cyclooctadienones, followed by hydrogenolysis, affords bridgehead substituted 9-azabicyclo[3.3.1]nonan-3-ones. Use of (+)-α-methylbenzylamine in the addition leads to mixtures of diastereomeric adducts in unequal amounts. Although the degree of asymmetric induction is low (10–20% ee), the diastereonomers can be easily separated, affording pure enantiomeric forms of the ladybug alkaloid adaline 1 and the Euphorbia alkaloid 3. 相似文献
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Condensation of 3-substituted 3-azabicyclo[3.3.1]nonan-9-ones with hydroxylamine and hydrazine hydrate gave the corresponding oximes, hydrazones, and azines. Reductive amination of the title compounds in the presence of sodium triacetoxyhydridoborate led to the formation of 3-substituted 3-azabicyclo[3.3.1]nonan-9-amines which were converted into the corresponding dihydrochlorides by treatment with dry hydrogen chloride. Treatment of 3-tert-butoxycarbonyl derivatives with HCl under analogous conditions was accompanied by elimination of the tert-butoxycarbonyl group to produce 3-azabicyclo[3.3.1]nonan-9-amine dihydrochlorides. 相似文献
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I. Iriepa B. Gil-Alberdi E. Galvez R. Torres P. Gomez-Sal J. Bellanato 《Journal of heterocyclic chemistry》1993,30(1):29-32
The infrared spectra in several media and the crystal structure of 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]-nonan-9β-ol ( I ) (Scheme I) have been determined, in order to complete the structural study described for the title compound from the 1H and 13C nmr data [1]. The bicyclic system adopts a flattened chair-chair conformation in which the cyclohexane ring is more flattened. The methyl and phenyl groups are in equatorial positions and the OH group in an axial position with respect to the piperidine ring. 相似文献
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G.F. Vafina G.R. Yakhina L.V. Spirikhin F.Z. Galin M.S. Yunusov 《Russian Journal of Organic Chemistry》2005,41(8):1208-1211
Reduction of 6-acetoxy-3-benzyl-l-ethoxycarbonyl-3-azabicyclo[3.3.1]nonan-9-one with sodium borohydride was investigated in various conditions. The stereochemistry of reduction products was deduced from 1H and 13C NMR and mass spectra. 相似文献
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Paramasivam Parthiban Paramasivam Rathika Keun Soo Park Yeon Tae Jeong 《Monatshefte für Chemie / Chemical Monthly》2010,19(7):79-93
Abstract
A series of differently substituted 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one oximes have been synthesized and their 1H and 13C NMR chemical shifts have been unambiguously assigned using H,H-COSY, NOESY, HSQC, and HMBC spectral data. On the basis of the NMR studies, irrespective of the nature and position of the substituents, all reported compounds exist in twin-chair conformation with equatorial disposition of the phenyl groups at C-2 and C-4 of the 3-azabicyclononane moiety. Among the synthesized oxime derivatives, compounds with halo-substituents at ortho/para positions of the phenyl showed good antifungal profile against all tested organisms. 相似文献14.
V. Ya. Vorob'eva E. E. Mikhlina K. F. Turchin L. N. Yakhontov 《Chemistry of Heterocyclic Compounds》1970,6(8):964-967
The synthesis of 1-azabicyclo[3.2.2]nonan-4-one has been effected by the reaction of quinuclidin-3-one with diazomethane.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 8, pp. 1037–1040, August, 1970. 相似文献
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Douglas J. Raber Christopher M. Janks Milton D. Johnston Nancy K. Raber 《Tetrahedron letters》1980,21(8):677-680
Lanthanide shift reagents have been used for the conformational analysis of bicyclo[3.3.1]-nonan-9-one. Comparison of predicted shifts and experimental values obtained with Eu(fod)3 indicate that the boat-chair conformation constitutes 22% of the mixture of conformers. 相似文献
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M. Zh. Buranbaev Yu. P. Gladii A. I. Gubin T. T. Omarov N. I. Zaporozhskaya B. M. Sultanbaeva N. S. Zefirov 《Chemistry of Heterocyclic Compounds》1990,26(10):1168-1170
A method is presented for synthesizing 6,6-dimethyl-2,4-diphenyl-3-aza-7-oxabicyclo[3.3.1]nonan-9-one. The x-ray structure shows that the compound in the crystal exists in the chair-boat conformation with the piperidine ring in the boat form. The two phenyl substituents in the 2- and 4-positions are responsible for such a conformation.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1400–1402, October, 1990. 相似文献
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N. J. Smeyers F. J. Melendez Y. G. Smeyers 《Journal of computational chemistry》1998,19(14):1567-1574
The potential energy hypersurfaces for the triple inversion, from chair to boat and α to β conformations, are explored theoretically in 3-azabicyclo[3.3.1]nonan-9-one and its N-methyl derivative, by using ab initio quantum-mechanical calculations. Both compounds are precursors of rigid analogs of the potential GABAA and GABAB receptor antagonists. In contrast to results from semiempirical calculations, the chair–chair β conformers are found to be, by far, the most stable structures for both the nonmethylated and N-methylated compounds. The inversion barriers are found to be relatively low, so that the conformers could be expected to exist in thermodynamic equilibrium at room temperature. A population analysis reveals, however, that, in the ab initio approach, the molecules seem to exist practically only in the chair–chair–β conformation. The theoretical results compare well with the available experimental data. © 1998 John Wiley & Sons, Inc. J Comput Chem 19: 1567–1574, 1998 相似文献
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3-Methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-α(β)-ols have been synthesized and studied by ir, 1H and 13C nmr spectroscopy. In deuteriochloroform and perdeuteriobenzene solutions, these compounds adopt a flattened chair-chair conformation in which the cyclohexane ring is more flattened. From the 1H and 13C nmr data, several stereoelectronic effects have been deduced. The complete and unambiguous assignment of all protons of the 3-azabicyclo[3.3.1]nonane system, not described up to date, has been carried out. 相似文献