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1.
Synthesis of RNA nucleobases from formamide is one of the recurring topics of prebiotic chemistry research. Earlier reports suggest that thymine, the substitute for uracil in DNA, may also be synthesized from formamide in the presence of catalysts enabling conversion of formamide to formaldehyde. In the current paper, we show that to a lesser extent conversion of uracil to thymine may occur even in the absence of catalysts. This is enabled by the presence of formic acid in the reaction mixture that forms as the hydrolysis product of formamide. Under the reaction conditions of our study, the disproportionation of formic acid may produce formaldehyde that hydroxymethylates uracil in the first step of the conversion process. The experiments are supplemented by quantum chemical modeling of the reaction pathway, supporting the plausibility of the mechanism suggested by Saladino and coworkers.  相似文献   
2.
The interactions of the nucleobases thymine (C5H6N2O2) and uracil (C4H4N2O2) with Cr‐doped C20 fullerene (C19Cr) are investigated by performing density functional theory calculations. The adsorption of these nucleobases on C19Cr leads to two distinct geometries (P1 and P2) differing in the orientation of the nucleobases. The interaction of the nucleobases with the C19Cr nanocluster is highly exothermic, revealing that they are chemically adsorbed on C19Cr. The results show that the binding energy of the thymine–C19Cr complex is slightly higher than that of the uracil–C19Cr complex. In addition, the P2 geometry is more stable compared to P1 due to the higher binding energy in the former configuration. However, based on the results of natural bond orbital and frontier molecular orbitals analyses, the C19Cr nanocage has higher reactivity with the nucleobases in P1 geometry in comparison with P2 due to the larger charge transfer and orbital hybridization in the former geometry. Moreover, the band gap of the C19Cr nanocage decreases after interaction with the nucleobases, and interestingly the impact is more pronounced for P1 geometry, confirming the higher sensitivity of C19Cr to the nucleobases in P1 geometry. Our findings reveal the promising potential of C19Cr as an organometallic carrier for nucleobases thymine and uracil.  相似文献   
3.
We have developed an efficient procedure and detection method using reversed‐phase high‐performance liquid chromatography for the simultaneous measurement of uracil and dihydrouracil in human plasma. The procedure, including chromatographic conditions and sample preparation, was optimized and validated. Optimization of the sample preparation included deproteinization, extraction, and cleanup. A new sample preparation method which resulted in an improved extraction yield of analytes and significantly reduced interference at low‐wavelength UV detection was developed. The developed method was validated for specificity, linearity, limits of detection and quantitation, precision, and accuracy. All calibration curves showed excellent linear regression (R 2 > 0.9990) within the testing range. The limit of detection for uracil and dihydrouracil was 2.5 and 5.0 ng/mL, respectively. The extraction yields were >94% for uracil and 91% for dihydrouracil. Intra‐ and interassay precision and accuracy for uracil and dihydrouracil were lower than 8% at all tested concentrations. The proposed method was successfully applied to measure plasma concentrations of uracil and dihydrouracil in colorectal cancer patients scheduled to receive fluoropyrimidine‐based chemotherapy.  相似文献   
4.
A facile synthesis of uracil‐Cu2+ nanoparticles immobilized on alpha‐zirconium hydrogen phosphate (α‐ZrP), abbreviated as α‐ZrP/Uracil/Cu2+, was presented. This compound was synthesized by the thermal method and used as a reusable catalyst for the Morita‐Baylis‐Hillman reaction without any additives. First, (3‐ iodopropyl) trimethoxysilane as a linker is reacted with α‐ZrP support to give the α‐ZrP/IPTMOS. Addition of uracil and then the addition of copper (II) acetate to α‐ZrP/IPTMOS results in the production of selected catalyst. The Morita‐Baylis‐Hillman reaction catalyzed by α‐ZrP/Uracil/Cu2 + demonstrated high product yield, short reaction time and a straightforward work‐up. The catalyst with enough outside surface was easily recovered using centrifugation and reused five times without a significant reduction in its activity.  相似文献   
5.
The mechanism of the decomposition of acryloylcarbamates 7a–b yielding highly reactive isocyanates 3a–b was proposed based on NMR measurements and quantum chemical calculations. A good agreement between the experimental kinetic data and DFT calculations allowed us to demonstrate that the stability of 7a–d depends on the presence of methyl in the acryloyl moiety and the position of the nitro group in the nitrophenolic part of the molecule. Furthermore, the reactivity of 7a–d with weakly nucleophilic and sterically hindered 2,4,6‐tri‐tert‐butylaniline was explored by 1H NMR demonstrating the usefulness of reagents 7a–d offering access to a variety of 1‐N‐substituted uracils and thymines with potentially interesting biological properties. Copyright © 2010 John Wiley & Sons, Ltd.  相似文献   
6.
Pyrimido[4,5-d]pyrimidine derivatives 4 have been prepared in an efficient and regioselective manner in water via multi-component reaction of isothiocyanate 1, aromatic aldehyde 2, N,N-dimethyl-6-amino uracil 3 in the presence of p-toluenesulfonic acid (p-TSA) as a Lewis acid catalyst.  相似文献   
7.
A convenient one‐step synthesis of 5‐aryl uracils has been developed. The procedure involves heating ethyl 3‐hydroxy‐2‐arylpropenate with urea at 130°C, followed by base‐catalyzed cyclization. The method is simple and high yielding.  相似文献   
8.
The sodium salts of the conjugated bases of uracils undergo highly chemoselective O4-monoalkylation when treated with various alkyl halides in dry DMF, while the use of methyl iodide results in N1+N3-dimethylation. Theoretical evaluations of the chemo- and regioselectivity along with X-ray crystallographic data are presented.  相似文献   
9.
An efficient synthesis of tetracyclic uracil derivatives (polycyclic pyrans) is achieved via domino Knoevenagel-hetero-Diels-Alder reactions of O-propargylated salicylaldehyde derivatives with 1,3-dimethylbarbituric acid in water as solvent in the presence of CuI. The products are formed in good yields.  相似文献   
10.
We have analyzed the vibrational spectra of uracil and its methyl-substituted derivatives using the DFT/B3LYP/6-31G(p,d) method, in the anharmonic approximation. We have shown that it is possible to use second-order anharmonic theory of vibrational spectra in predictive calculations for substituted uracils. __________ Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 73, No. 4, pp. 431–436, July–August, 2006.  相似文献   
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