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1.
A facile method for the nucleophilic hydroxylation of alkyl halides and mesylates with water has been developed in which the use of ionic liquid as an alternative reaction medium not only enhanced the nucleophilicity of water but also reduced the formation of elimination products predominantly formed under the conventional basic reaction conditions. For example, hydroxylation of model compound 2-(3-bromopropyl)naphthalene (1) to 2-(3-hydroxypropyl)naphthalene (2) with water in 1-n-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF(4)]) and 1,4-dioxane proceeded selectively in high yield (94%). The reactivity of other nucleophilic oxygen sources such as alcohol, phenol, and acetic acid in an ionic liquid was also investigated.  相似文献   

2.
Xu  Li  Zhou  Tao  Zhang  Jian-Duo  Deng  Le-Le  Jiang  Jia-Rui  Yang  Wen-Wu  Liu  Chun-Bo  Kong  Wei-Song  Li  Xue-Mei  Yang  Guang-Yu  Hu  Qiu-Fen  Liu  Xin 《Chemistry of Natural Compounds》2021,57(6):1047-1050
Chemistry of Natural Compounds - Two new isoindolin-1-ones, 6-(3-hydroxypropyl)-2,4-dimethylisoindolin-1-one (1) and 4-(hydroxymethyl)-6-(3-hydroxypropyl)-2-methylisoindolin-1-one (2), were...  相似文献   

3.
Reactions of 1,3-bis(3-chloro-2-hydroxypropyl)uracil, 1,3-bis(3-chloro-2-hydroxypropyl)-6-methyluracil, 1,3-bis(3-chloro-2-hydroxypropyl)-5-hydroxy-6-methyluracil, and 1,3-bis(3-chloro-2-hydroxypropyl)-5-fluorouracil with 2-amino-4-methylthiobutanoic acid (methionine) were studied for the first time.  相似文献   

4.
The protected 2-formyl-L-arabinal 2 reacted with thiourea and cyanamide in the presence of sodium hydride to afford via ring transformations the 5-[1R,2S-1,2- bis(benzyloxy)-3-hydroxypropyl]-1,2-dihydropyrimidines 3 and 4, respectively. Similarly, treatment of 2 with 3-amino-2H-1,2,4-triazole yielded 6-[1R,2S-1,2- bis(benzyloxy)-3-hydroxypropyl][1,2,4]-triazolo[1,5-a]pyrimidine (5).  相似文献   

5.
A series of 6-aryl-3-(3-hydroxypropyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]-thiadiazines were synthesized by the reaction of 4-amino-3-(3-hydroxypropyl)-5-mercapto-1,2,4-triazole (1) with substituted omega-haloacetophenones. Their structures were confirmed by elemental analysis, IR, 1H-NMR, and 13C-NMR. Tests of plant growth regulating effects showed that the title compounds display remarkable inhibitory activities on the growth of radish and wheat.  相似文献   

6.
From the crinoid Comanthus bennetti we isolated and characterized five pigments. One is the known 3-(1′-hydroxypropyl)-1,6,8-trihydroxy-9,10-anthraquinone (rhodoptilometrin). The remaining four had not previously been isolated from a natural source: 3-propyl-1,6,8-trihydroxy- 9,10-anthraquinone; 3-propionyl-1,6,8-trihydroxy-9,10-anthraquinone; 3(2′-hydroxypentyl)-1,6,8- trihydroxy-9,10-anthraquinone; and 2-(1′-hydroxypropyl)-1,4,5,7-tetrahydroxy-9,10-anthraquinone.  相似文献   

7.
The reactivity of 4-aryl-1-(2-chloroethyl)azetidin-2-ones and 4-aryl-1-(3-bromopropyl)azetidin-2-ones with regard to lithium aluminium hydride has been evaluated for the first time. 4-Aryl-1-(2-chloroethyl)azetidin-2-ones were transformed into novel 1-(1-aryl-3-hydroxypropyl)aziridines through an unprecedented conversion of beta-lactams into 2,3-unsubstituted aziridine derivatives. Unexpectedly, 4-aryl-1-(3-bromopropyl)azetidin-2-ones underwent dehalogenation towards 3-aryl-3-(N-propylamino)propan-1-ols upon treatment with LiAlH(4). 1-(1-Aryl-3-hydroxypropyl)aziridines were further elaborated by means of ring opening reactions using benzyl bromide in acetonitrile towards 3-aryl-3-[N-benzyl-N-(2-bromoethyl)amino]propan-1-ols and using aluminium(iii) chloride in diethyl ether, affording 3-aryl-3-[N-(2-chloroethyl)amino]propan-1-ols.  相似文献   

8.
电极/离子液体界面电容   总被引:1,自引:0,他引:1  
用电化学阻抗方法研究了铂片电极在BMIMPF6,BMIMBF4,BMIMClO4,BMIMTf2N,BMIMCl,BMIMBr,C3OHMIMBF4,C3OHMIMClO4和BMMIMPF6(BMIM:1-butyl-3-methylimidazolium;C3OHMIM:1-(3-hydroxypropyl)-3-methylimidazolium;BMMIM:1-butyl-2-methyl-3-methylimidazolium;Tf2N:bis(trifluoromethylsulfonyl)amide)等离子液体中的界面电容及结构.结果表明:当阴、阳离子半径相差不大且不存在特性吸附时,在零电荷电势附近,电极/离子液体界面的电容-电势曲线将出现电容单峰或者双峰.电极的零电荷电势对应于单峰的峰电势或者双峰之间的谷电势.当电极电势远离零电荷电势时,电极/离子液体界面成紧密层结构,可由紧密层理论来描述.如果存在离子的特性吸附,相应的电容峰可能不再出现,而表现为双层电容随电极电势对零电荷电势的偏离而单调增加.还研究了添加小的Li+离子对电极/离子液体界面电容的影响.通过向BMIMTf2N中加入LiTf2N,发现Li+离子可以改变电极/离子液体界面的双层结构,但无助于界面电容的提高,甚至可能引起电容的降低.最后探讨了不同条件下,尤其考虑阴阳离子特性吸附时,电极/离子液体的界面结构.  相似文献   

9.
以氯乙酰氯和对碘苯胺为原料,经酰化合成了4-碘-氯乙酰苯胺,接着与1-甲基咪唑反应得到氯化1-甲基-3-(4-碘苯氨基甲酰甲基)咪唑钅翁,随后在水溶液中发生阴离子交换,合成了1-甲基-3-(4-碘苯氨基甲酰甲基)咪唑四氟硼酸盐;四氟硼酸盐在过氧化氢/三氟乙酸酐体系中氧化得到一种新的离子液体负载的双(三氟乙酰氧基)碘苯试剂1-甲基-3-[4-双(三氟乙酰氧基)碘苯氨基甲酰甲基]咪唑四氟硼酸盐。反应总收率62.3%。试剂没有吸湿性,在空气中长期放置不变质。化学结构用IR、1H NMR、13C NMR、19F NMR和元素分析表征。  相似文献   

10.
We have used the high nucleophilicity of bromide ion in the form of the ionic liquid, 1-n-butyl-3-methylimidazolium bromide ([bmim][Br]), for the nucleophilic displacement of an alkyl group to regenerate a phenol from the corresponding aryl alkyl ether. Using 2-methoxynaphthalene (1) as a model compound, we found that the combination of ionic liquid [bmim][Br] and p-toluenesulfonic acid with warming effected demethylation in 14 h, affording the desired product 2-naphthol (2) in good yield (97%). Various other protic acids (MsOH, hydrochloric acid (35%), dilute sulfuric acid (50%)) could be used as a proton source in this demethylation reaction. Under the same conditions, cleavage of alkyl alkyl ether 2-(3-methoxypropyl)naphthalene yielded mixture of corresponding 2-(3-bromopropyl)naphthalene and 2-(3-hydroxypropyl)naphthalene. Dealkylation of various aryl alkyl ethers could also be achieved using significantly reduced (i.e., stoichiometric) amounts of concentrated hydrobromic acid (47%) in the ionic liquid. Both procedures afforded the desired products in moderate to good yield; however, cleavage of aryl alkyl cyclic ether, 2,3-dihydrobenzofuran, resulted in low yield of the desired product o-2-bromoethylphenol. The convenience of this method for ether cleavage and its effectiveness using only a moderate excess of hydrobromic acid make it attractive as a green chemical method.  相似文献   

11.
采用荧光光谱和紫外吸收光谱研究了羟基功能化离子液体1-(1,2-二羟基丙基)-3-甲基咪唑氯盐([2,3-dhpmim]Cl)、1-(1,2-二羟基丙基)-3-甲基咪唑四氟硼酸盐([2,3-dhpmim]BF4)、1-(1,2-二羟基丙基)-3-甲基咪唑六氟磷酸盐([2,3-dhpmim]PF6)与溶菌酶的相互作用。研究发现此3种离子液体对溶菌酶的荧光猝灭均为静态猝灭;同步荧光显示离子液体与溶菌酶肽链上的色氨酸残基作用,色氨酸残基微环境发生改变;结合常数和结合位点数按照[2,3-dhpmim]Cl、[2,3-dhpmim]BF4、[2,3-dhpmim]PF6顺序依次增大,并随温度的升高而增大。  相似文献   

12.
The catalytic hydrogenation of 5-(3-hydroxypropyl)-1,2-dihydropyrrolizines gave a mixture of stereoisbmers of 3(5)-(3-hydroxypropyl)pyrrolizidines, which was separated successfully. The stereochemistry of the compounds obtained was determined by means of the IR and 13C NMR spectra. The presence of strong intramolecular hydrogen bonds was detected. The basicities of the compounds obtained were determined.See [1] for Communication 19.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 63–67, January, 1980.  相似文献   

13.
1-Hydrazino-2-propanol reacts with aliphatic carbonyl compounds to form the corresponding (2-hydroxypropyl)hydrazones. 1-(N-Alkylhydrazino)-2-propanols, on the other hand, give tautomeric mixtures of alkyl-substituted perhydro-1,3,4-oxadiazines and N-alkyl-N-(2-hydroxypropyl)hydrazones. As compared with derivatives of 2-(N-alkylhydrazino)ethanols, the position of the equilibrium in the investigated cases is shifted to favor the cyclic forms.See [1] for communication I.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 301–308, March, 1971.  相似文献   

14.
Ionic liquids are attracting growing interest as alternatives to conventional molecular solvents. Experimental values of vapor pressure, enthalpy of vaporization, and enthalpy of formation of ionic liquids are the key thermodynamic quantities, which are required for the validation and development of the molecular modeling and ab initio methods toward this new class of solvents. In this work, the molar enthalpy of formation of the liquid 1-butyl-3-methylimidazolium dicyanamide, 206.2 +/- 2.5 kJ.mol-1, was measured by means of combustion calorimetry. The molar enthalpy of vaporization of 1-butyl-3-methylimidazolium dicyanamide, 157.2 +/- 1.1 kJ.mol-1, was obtained from the temperature dependence of the vapor pressure measured using the transpiration method. The latter method has been checked with measurements of 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide, where data are available from the effusion technique. The first experimental determination of the gaseous enthalpy of formation of the ionic liquid 1-butyl-3-methylimidazolium dicyanamide, 363.4 +/- 2.7 kJ.mol-1, from thermochemical measurements (combustion and transpiration) is presented. Ab initio calculations of the enthalpy of formation in the gaseous phase have been performed for 1-butyl-3-methylimidazolium dicyanamide using the G3MP2 theory. Excellent agreement with experimental results has been observed. The method developed opens a new way to obtain thermodynamic properties of ionic liquids which have not been available so far.  相似文献   

15.
Properties of the surface of ionic liquids, such as surface tension, ordering, and charge and density profiles, were studied using molecular simulation. Two types of modification in the molecular structure of imidazolium cations were studied: the length of the alkyl side chain and the presence of a polar hydroxyl group at the end of the side chain. Four ionic liquids were considered: 1-ethyl-3-methylimidazolium tetrafluoroborate, [C(2)C(1)im][BF(4)]; 1-(2-hydroxyethyl)-3-methylimidazolium tetrafluoroborate, [C(2)OHC(1)im][BF(4)]; 1-octyl-3-methylimidazolium tetrafluoroborate, [C(8)C(1)im][BF(4)] and 1-(8-hydroxyoctyl)-3-methylimidazolium tetrafluoroborate, [C(8)OHC(1)im][BF(4)]. The surface tension was calculated using both mechanical and thermodynamic definitions, with consistent treatment of the long-range corrections. The simulations reproduce the available experimental values of surface tension with a maximum deviation of ±10%. This energetic characterization of the interface is completed by microscopic structural analysis of orientational ordering at the interface and density profiles along the direction normal to the interface. The presence of the hydroxyl group modifies the local structure at the interface, leading to a less organized liquid phase. The results allow us to relate the surface tension to the structural ordering at the liquid-vacuum interface.  相似文献   

16.
The objective of this work was to explore the feasibility of using ionic liquids (ILs), namely N-ethyl-N-methylmorpholinium dicyanamide, [EMMor][DCA], (3-hydroxypropyl)-1-methylmorpholinium dicyanamide, [N-C3OHMMor][DCA], 1-(3-hydroxypropyl)-3-methylimidazolium dicyanamide, [N-C3OHMIM][DCA], 1-(3-hydroxypropyl)pyridinium dicyanamide, [N-C3OHPy][DCA], (3-cyanopropyl)pyridinium dicyanamide, [N-C3CNPy][DCA], and (3-cyanopropyl)methylpyrrolidinium dicyanamide, [N-C3CNMPyr][DCA] for the separation of ethylbenzene and styrene. The liquid–liquid equilibrium (LLE) data in ternary systems of {IL (1)?+?styrene (2)?+?ethylbenzene (3)} at T?=?298.15 K and ambient pressure is presented for the six ILs synthesized by us. The final chromatography analysis of the composition of tie-lines has shown that the studied ILs are not found in the raffinate phase and they show interesting results on the selectivity and solute distribution ratio for styrene extraction. A comparison of different ILs is presented for the studied separation problem. It was observed that the best separation selectivities were found for [N-C3CNPy][DCA] (SAv?=?2.38) and [N-C3OHMMor][DCA] (SAv?=?2.42) in comparison with other studied ILs in this work and those presented in the literature. While the data presented here are useful from a theoretical standpoint, the possibility of applications for these ILs in technological processes is questionable because of low solute distribution ratios, especially those calculated from the masses [N-C3CNPy][DCA] (βMAv?=?0.08) and [N-C3OHMMor][DCA] (βMAv?=?0.07). The experimental tie-lines were correlated with the non-random two liquid NRTL model.  相似文献   

17.
The effects of ionic liquids 1-(2-aminoethyl)-3-methylimidazolium chloride ([MimAE]Cl), 1-carboxylmethyl-3-methylimidazolium chloride ([MimCM]Cl), 1-(2-hydroxylethyl)-3-methylimidazolium chloride ([MimHE]Cl), and 1-ethyl-3-methylimidazolium chloride ([Emim]Cl) on the physicochemical properties of aqueous sodium dodecyl sulfate (SDS) solutions were studied. Compared with [Emim]Cl, the presence of amino group can further facilitate the micellization of SDS, while the opposite result is observed as carboxyl group is imparted. No obvious changes in critical micelle concentration (CMC) and $ {\gamma_{\mathrm{CMC}}} $ values are induced by the neutral hydroxyl group. Only the addition of [MimAE]Cl drastically increases the micellar size. Significant decrease in CMC and increase in micellar size were observed with decreasing pH of [MimAE]Cl solution. The increase in pH of [MimCM]Cl solution results in a slight increase in CMC and decrease in micellar size. 1H NMR spectra revealed the amino groups are adsorbed at the micellar surface, while the carboxyl groups/carboxylate ions and hydroxyl groups tend to point towards bulk water.  相似文献   

18.
何德良  张泉 《高分子科学》2014,32(2):163-168
A new type of polymerizable ionic liquid (IL) 1-(3-aminobenzyl)-3-methylimidazolium chloride (AMIC) was synthesized to obtain a novel polymer salt poly(1-(3-aminobenzyl)-3-methylimidazolium chloride) (PAMIC). The AMIC was structurally characterized by mass spectrometry and Fourier transform infrared spectrometry (FTIR). The structure, morphology and properties of PAMIC were investigated by FTIR, ultraviolet visible absorption spectra (UV-Vis), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), conductivity measurement and thermo- gravimetric analysis (TGA). The PAMIC was spherulitic with an average diameter of about 50 nm and showed high conductivity and excellent thermal stability.  相似文献   

19.
Research on Chemical Intermediates - 3-[(3-(Trisilyloxy)propyl)chloride]-1-methylimidazolium tribromide ionic liquid supported on MCM-41 [nano-MCM-41@(CH2)3-1-methylimidazole]Br3 as a novel...  相似文献   

20.
Well-resolved ESR-spectra of the methylviologene radical cation (MV*+) are recorded in room-temperature liquid ions as solvents. The temperature dependences of the ESR-coupling constants are similar to those measured in classical organic solvents. Electron-self exchange rates are reported for the methylviologene redox couple (MV++/MV*+) in 1-butyl-3-methylimidazolium hexafluorophosphate (bmim+ PF6-), 1-butlyl-3-methylimidazolium fluoroborate (bmim+ BF4-) and 1-ethyl-3-imidazolium ethylsulfate (emim+ O3SOEt-) within a temperature range of 350 K < or = T < or = 460 K. The diffusion controlled rate constants observed vary between 8.2 x 10(7) M(-1) s(-1) and 1.2 x 10(9) M(-1) s(-1). From temperature-dependent measurements the activation energies obtained range from 27.4 kJ/mol in emim+ O3SOEt- to 42.1 kJ/mol in bmim+ PF6-, respectively.  相似文献   

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