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1.
Moonyong Shin Myeong Hak Kim Tae-hwan Ha Jongho Jeon Kyoo-Hyun Chung Jin Seuk Kim Young Gyu Kim 《Tetrahedron》2014
Propellanes and azapropellanes are attractive compounds for their unique structure and valuable applications but there are few synthetic studies for highly N-substituted azapropellanes. Several novel derivatives of 2,4,6,8,10-pentaaza[3.3.3]propellane, such as 3, 4, and 5 were successfully synthesized from readily available diethyl tartrate. Most of the synthetic steps were efficient. Their propellane structures were established by spectroscopic data and confirmed with single crystal X-ray analyses. 相似文献
2.
3,7,10-Tribenzyl-3,7,10-triaza[3.3.3]propellane ( 4a ), 3,7-dibenzyl-10-phenyl-3,7,10-triaza[3.3.3]propellane ( 4c ), 3,7-dibenzyl-10-(p-tolyl)-3,7,10-triaza[3.3.3]propellane ( 4b ), and 3-oxa-7,10-diaza[3.3.3]propellane ( 6 ) have been prepared. 相似文献
3.
A shorter and significantly higher-yield procedure for the preparation of bicyclo[3.3.3]undecane (manxane) is reported. 相似文献
4.
The crystal structure of bicyclo [3.3.3]undecane-1,5-diol has been determined. It is monoclinic, P21/c, a = 12.99(2), b = 14.16(2), c = 12.50(1)A,β = 112.42(2)°, with two independent molecules in the asymmetric unit. One of these is disordered, but the other has almost exact C3h symmetry and its conformation and precise molecular geometry agree well with previous calculations by molecular mechanics. The molecule shows considerable angle strain, having bridge angles in the range 118–121° 相似文献
5.
Shubina T. E. Gunchenko P. A. Vigovskaya T. S. Schreiner P. R. Yurchenko A. G. Fokin A. A. 《Theoretical and Experimental Chemistry》2002,38(4):229-236
The structure of [3.3.2]- and [3.3.3]propellanes, their framework analogs, and their radical-cations was investigated by computational methods (BLYP and B3LYP) in the 6-31G* basis set. The reactivity of the propellanes toward model oxidizing electrophiles does not contradict the quantum-chemical calculations. In the case of the tetracyclic framework analog of [3.3.3]propellane the reaction takes place as C—H substitution, whereas in the case of [3.3.2]propellanes it takes place as C—C-oxidative addition. 相似文献
6.
From a study of the 1H NMR spectra of a number of 3,7-disubstituted derivatives of 1,3,5,7-tetraazabicycio - [3.3.1] - nonane it is concluded that these molecules exist in either chair-chair or flattened chair-chair conformations. The derivatives containing COCH3 and NO substitutents have room temperature spectra consistent with restricted rotation about their NC and NN bonds respectively. High temperature spectra reveal an activation energy, for the rotational barrier of the NC bond in the diacetyl derivative, of 23±2K.Cal/mol. 相似文献
7.
A highly chemoselective heteroannulation protocol for the synthesis of unreported polysubstituted heterocyclic [3.3.3]propellanes has been developed by sequential four-component reaction of ninhydrin, malononitrile, primary amines, and dialkyl acetylenedicarboxylates under mild conditions in water. To the best of our knowledge, there are no previous reports for the synthesis of these classes of heterocyclic [3.3.3]propellanes. The merit of this sequential Knoevenagel condensation/enamine formation/Michael addition/cyclization sequence is highlighted by its high atom-economy, excellent yields, the use of water as reaction media, and the efficiency of production without the use of any activator or metal promoters. This synthesis serves as a nice addition to group-assistant-purification (GAP) chemistry in which purification via chromatography and recrystallization can be avoided, and the pure products were obtained simply by washing the crude products with 95% ethanol. 相似文献
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11.
Reyes-Trejo B Morales-Ríos MS Joseph-Nathan P 《Magnetic resonance in chemistry : MRC》2007,45(4):346-350
Formation of (-)-[4.3.3]propellane 4 from (-)-14-hydroxymodhephene (2) proceeds through a Wagner-Meerwein rearrangement via C3--C4 bond-shift to give a stable intermediate, dimethylcyclohexadienyl cation A, which undergoes deprotonation. Herein, this mechanism was investigated by using a deuterium labeled substrate at the C-14 methylene group of (-)-2, which was incorporated into the C-4 position of (-)-[4.3.3]propellane 4. The stereostructure of (-)-4 was investigated by applying a combination of NMR experimental and theoretical approaches. 相似文献
12.
E. N. Ulomskii E. V. Tsoi V. L. Rusinov O. N. Chupakhin G. L. Kalb I. M. Sosonkin 《Chemistry of Heterocyclic Compounds》1992,28(5):570-573
Reduction of6-nitro-7-oxo-4,7-dihydroazolo[5,1-c][1,2,4]triazines into the corresponding amines with sodium dithionite takes place smoothly in neutral aqueous solutions. The structural effects in reduction of nitroazoloazines were evaluated electrochemically.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 674–677, May, 1992. 相似文献
13.
The title diketone was reduced to give a mixture of the three possible diols which were isolated and characterized. 相似文献
14.
[reaction: see text] Several calix[4]arene derivatives propylated on the lower rim and substituted on the upper rim with amino or carboxyl groups have been synthesized. Examples include calixarenes substituted with alanino (C- and N-linked), amino, carboxy, carboxyphenyl, and amidino groups. The self-assembly of these derivatized calixarenes into heterodimers has been studied by NMR in DMSO-d(6) or CD(3)OD with 5% aqueous phosphate buffer. 相似文献
15.
Paula M. Marcos José R. Ascenso Roger Lamartine J. L. C. Pereira 《Supramolecular chemistry》2013,25(3-4):303-306
Abstract The tetramethyl (2) and tetraethyl (3) ethers, and the tetraacetate (4) derivatives of the p-tert-butyldihomooxacalix[4]arene were prepared. The mobility of these compounds studied by temperature-dependent 1H NMR spectroscopy. For the tetraacetate derivative, at room temperature, 1,2- or 1,3-alternate conformations are suggested. Those conformations were confirmed by NOE difference and COSY spectra for the tetraethyl ether derivative in CDCl3 at -20°C. 相似文献
16.
Claude Marfisi Michle Cossu Jean-Pierre Aycard 《Magnetic resonance in chemistry : MRC》1981,17(4):239-241
A series of 6-X-3,8-dioxatricyclo[3.2.1.02,4]octanes (X?CO2CH3, CN, Cl and CN) are studied by NMR, after their syntheses by epoxidation of the corresponding 7-oxabicyclo[2.2.1]heptenes. The NMR parameters (J, δ) are determined, and also the anisotropy effects of methyl groups at the 1,5 bridgehead positions. The results allow an unambiguous identification of the diastereo-isomers having a gem-chlorocyano group in the 6 position. 相似文献
17.
James R. Beck 《Journal of heterocyclic chemistry》1975,12(5):1037-1038
18.
Byeongil Lee Moonyong Shin Youngran Seo Myeong Hak Kim Hye Ryoung Lee Jin Seok Kim Kyu-hyun Chung Dongwon Yoo Young Gyu Kim 《Tetrahedron》2018,74(1):130-134
Azapropellanes are of great interest in many disciplines, including materials science and medicinal chemistry. Various synthetic approaches for azapropellanes have been explored; however, the synthetic study of the polyazapropellane skeleton containing five or more nitrogen atoms is rare. Here, we report a simple yet highly efficient protocol for the synthesis of the hexaaza[3.3.3]propellane skeleton as a building block for high energy materials for the first time. The key reactions include the Boc2O-assisted cyclization of glycoluril diamine without a column purification step and the first full reduction of all the three carbonyl groups to the methylene groups through a combination of LiAlH4 and DIBAL-H. All the structures were confirmed by spectroscopic and X-ray analyses. 相似文献
19.
Maciej PisklakFranciszek Herold Romana Anulewicz-OstrowskaIwona Wawer 《Journal of Molecular Structure》2002,605(1):85-92
13C cross-polarisation magic angle spinning NMR data have been reported for four derivatives of 4-aryl-octahydro-pyrido[1,2-c]pyrimidine-1,3-dione and the X-ray diffraction data for two (with 2′-Me and 2′-OMe). The crystal structures show the presence of centrosymmetric cyclic dimers with intermolecular C1O?H-N or C3O?H-N hydrogen bonds, the configuration at the chiral centres (C4 and C4a) was determined as RR (SS). The twisting of aromatic ring at C4 with respect to the pyrido[1,2-c]pyrimidine skeleton is about 68-109°. 相似文献
20.
The functionalized dispiro[3.0.3.3]undecanes 6 and 7 undergo cascade rearrangements to yield the [3.3.3]propellanes 15 and 11, respectively. The formation of 15 proceeds via the bicyclic enone 16. 相似文献