中国化学快报

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Synthesis of new chiral 1,2,3,4-tertrahydroisoquinoline β-amino alcohol for asymmetric diethylzinc addition to aryl aldehydes (I)

Geng Xu, Zhan Zhu Liu

中国化学快报. 2009, 20(12): 1393-1396. https://doi.org/10.1016/j.cclet.2009.06.040

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Four new chiral 1,2,3,4-tetrahydroisoquinoline-derived β-amino alcohols were synthesized from commercially available L-DOPA.These ligands were evaluated in the asymmetric addition of diethylzinc to benzaldehydes and showed different catalytic activities (up to 86% ee).The solvent played an important role in the enantioselective process.The transition state models were proposed to explain the reversion of the product configuration.

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A practical synthesis of trifluorophenyl R-amino acid:The key precursor for the new anti-diabetic drug sitagliptin

Li Li Zeng, Ying Jie Ding, Gui Cheng Zhang, Hong Rui Song, Wen Hui Hu

中国化学快报. 2009, 20(12): 1397-1399. https://doi.org/10.1016/j.cclet.2009.06.036

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Sitagliptin is the first new anti-diabetic drug in DPP-IV inhibitor class.The general synthesis of sitagliptin is by coupling of the β-amino acid fragment with the heterocycle fragment.Though the specific β-amino acid can be easily made from the corresponding R-amino acid by Arndt-Eistert homologation, the optically pure precursor R-amino acid is difficult to prepare.We herein reported a practical protocol to make the trifluorophenyl substituted R-amino acid 4 in >99.9% ee and 40.3% yield by the enzymatic resolution employing enantioselective hydrolysis and a general separation procedure.This protocol requires only cheap starting materials and friendly reaction condition.The procedure not only allows people to prepare the drug substance, but also provides an alternative method for prepareing the rare a-amino acid and the subsequent β-amino acid.

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Baeyer-Villiger oxidation of cyclic ketones utilizing potassium peroxydisulfate (K₂S₂O₈) or sodium perborate (NaBO₃)in acidic media

S.Zarrabi, N.O.Mahmoodi K.Tabatabaeian, M.A.Zanjanchi

中国化学快报. 2009, 20(12): 1400-1404. https://doi.org/10.1016/j.cclet.2009.07.007

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The efficient, green, facile, mild and straightforward conversion procedure for the oxidation of cyclic ketones to lactones at room temperature utilizing potassium peroxydisulfate (K₂S ₂O₈) in acidic media is satisfactory to high yields without using traditional chlorinated solvents is reported.This oxidative reagent is cheap and friendly environmental procedure for industrial purposes than use of organic peracids.

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Microwave-promoted solvent-free synthesis of N-(diphenylmethylene)glycine alkyl esters

Quan Jun Wang, Wei He, Qiao Feng Wang, Xin Shi, Xiao Li Sun, Sheng Yong Zhang

中国化学快报. 2009, 20(12): 1405-1407. https://doi.org/10.1016/j.cclet.2009.06.019

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The efficient synthesis of N-(diphenylmethylene) glycine alkyl esters was achieved for the first microwave irradiation under solvent-free condition, using PEG or quaternary ammonium salts as phase transfer catalysts (PTCs).Under the optimum conditions,N-(diphenylmethylene) glycine alkyl esters were obtained in excellent yields in most cases.

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A simple and efficient synthesis of 2-substituted benzothiazoles catalyzed by H₂O₂/HCl

Hong Yun Guo Ji Chao Li, You Le Shang

中国化学快报. 2009, 20(12): 1408-1410. https://doi.org/10.1016/j.cclet.2009.06.037

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A simple and efficient procedure for the synthesis of substituted benzothiazoles through condensation of 2-aminothiophenol with aromatic aldehydes in the presence of H ₂O₂/HCl system in ethanol at room temperature is described.The target compounds have been characterized by ¹H NMR,¹³C NMR, IR and MS.Short reaction time, easy and quick isolation of the products, and excellent yields are the main advantages of this procedure.

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Synthesis of bis-indolylmethanes catalyzed by oxone

Cai Li Zhang, Zhi Qiang Du

中国化学快报. 2009, 20(12): 1411-1444. https://doi.org/10.1016/j.cclet.2009.06.021

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Oxone (3.5 mol%) was found to be an effective catalyst for the condensation reactions of indoles with aldehydes to afford bisindolylmethanes in good to excellent yields within 10-30 min.The method is simple and economic.The catalyst is found to be recyclable.

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Synthesis and photochemistry of novel bromo substituted stilbene derivatives as triplet state sensitizers for the generation of singlet oxygen

Hong Ru Li Qin Yuan Guo, Ting Xie, Fang Gao Sheng Tao Zhang

中国化学快报. 2009, 20(12): 1415-1418. https://doi.org/10.1016/j.cclet.2009.06.033

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We have presented the synthesis and characterization of three new bromo substituted stilbene derivatives, p-3,4,5-trimethoxy-p'-2,3,4,5,6-pentabromo st abromo stilbene(C1), p-N,N-dimethylamino-p'-2,3,4,5,6-pentabromo stilbene (C2) and 2013/5/18 23:53 p-N,N-diphenylamino-p'-2,3,4,5,6-pentabromo stilbene (C3) in this letter.The UV/vis absorption and photoluminescence were investigated in various solvents.The maximal absorption wavelength of C1 exhibited blue-shift to those of C2 and C3 in different solvents.No florescence emission could be detected for these compounds at room temperature.Singlet oxygen could be efficiently produced with thesesensitizers under near-ultraviolet and visible light irradiation.

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Novel four-hydrogen-bond assembled oligoamide dimer with pyrazoline moieties and its photoluminescent propertie

Guang Dong Lei, Ming Li, De Min Qiu, Hui Liu, Yan Huang, Zhi Yun Lu

中国化学快报. 2009, 20(12): 1419-1422. https://doi.org/10.1016/j.cclet.2009.06.034

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In this paper, the synthesis and characterization of a triarylpyrazoline modified four-H-bonded molecular duplex are described.Its molecular structure has been confirmed by ¹H NMR and ESI-MS.The duplex emits strong pure blue light peaking at 448 and 452 nm under UV photoexcitation in solution and solid state, respectively, and its relative photoluminescence quantum efficiency in solution is determined as 0.778 using quinine sulfate as reference.In concentration of >40 mmol/L, the duplex can gelate DMSO,and the organogel formed shows good pure blue photoluminescence too.This novel duplex, for its well-defined structure andefficient photoluminescence property, is a prospective candidate for pure blue electroluminescent emitter.

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Synthesis, liquid crystalline and luminescent properties of trimeric phenylenevinylene with end-groups of (R)-(+)-2-methylbutyric acid ester

Cheng Bo Zhang, Ying Li, Wen Ke Liu, Hai Quan Zhang, Huai Yang, Qing Shan Li, Guang Zhong Xing

中国化学快报. 2009, 20(12): 1423-1426. https://doi.org/10.1016/j.cclet.2009.06.022

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The trimeric phenylenevinylene with the symmetrical chiral end-groups (ChTPV) was synthesized.The liquid crystalline and luminescent properties of the ChTPV have been studied by differential scanning calorimetry (DSC), polarized optical microscopy (POM), absorption and photoluminescence spectra.The results indicated that the ChTPV exhibits mesophase over a wide temperature range and a typical optical texture of smectic phase.In contrast with the spectra of the solution, that of the film showed blue-shift in maximal absorption and red-shift in maximal emission due to H-type aggregation with parallel alignment of the TPV transition dipole moment.

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A novel and facile one-pot sulfonyloxylactonization of alkenoic acids

Min Zhu Li Ll, Cai Qin Liu

中国化学快报. 2009, 20(12): 1427-1430. https://doi.org/10.1016/j.cclet.2009.06.015

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The novel and facile one-pot method for sulfonyloxylactonization of alkenoic acids was reported:when (diacetoxyiodo)-benzene, various 4-pentenoic acids or 5-hexenoic acid and sulfonic acids were mixed in CH ₂Cl₂ at room temperature,sulfonyloxylactons were obtained in good to excellent yields in short times, some had two diastereoisomers.

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Synthesis and cytotoxicity of novel podophyllotoxin derivatives

Yi Zheng, You Guang Sun, Yuan Zhang, Jing Jing Lv, Wen Chao Bi, Yuan Wei Ma, Hong Chen

中国化学快报. 2009, 20(12): 1431-1434. https://doi.org/10.1016/j.cclet.2009.07.022

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In order to find novel synthetic antitumor agents with superior cytotoxicity and overcoming multidrug resistance, a novel series of 4β-N-substituted podophyllotoxin derivatives were synthesized and evaluated as potential antitumor agents.Seven novel podophyllotoxin derivatives were synthesized by linking 4β-amino-4-deoxypodophyllotoxin with N-substituted 5-methylindol-3-yl-glyoxyl chlorides and tested against K562 and K562/A02 using SRB methods in vitro, KB and KBV using MTT methods in vitro.

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Influence of terminal alkyl chain length on helical twisting property of chiral 1,2-propanediol derivatives

Wei Huang, Xiao Guang Zhang, Guang Da Yang, Zhen Yu Bian, Xiao Juan Wu, Guo Jing Ma, Qi Huang, Huai Yang

中国化学快报. 2009, 20(12): 1435-1438. https://doi.org/10.1016/j.cclet.2009.06.016

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In this study, a novel series of chiral 1,2-propanediol derivatives with different terminal alkyl chain length were synthesized and characterized by FT-IR,¹H NMR and DSC.After doped into a nematic liquid crystal host, all the chiral dopants induced chiral nematic liquid crystals exhibiting a helix inversion with temperature variation.The results indicate that terminal alkyl chain length has a prominent influence on helical twisting property of the chiral dopants.With increasing the terminal alkyl chain length, the molecular twisting power increases, the helix inversion temperatures varies slightly while the phase transition temperature decreases.An odd-even effect may exist in the molecular twisting power of the chiral dopants.

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A mild, efficient and selective iodination of aromatic compounds using iodine and 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate

Rashid Badri Maryam Gorjizadeh

中国化学快报. 2009, 20(12): 1439-1443. https://doi.org/10.1016/j.cclet.2009.06.017

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A simple and efficient method for the iodination of aromatic compounds has been achieved in the presence of iodine and 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate.

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Silica-bonded S-sulfonic acid a recyclable catalyst for the synthesis of coumarins

Khodabakhsh Niknam, Dariush Saberi, Mojtaba Baghernejad

中国化学快报. 2009, 20(12): 1444-1448. https://doi.org/10.1016/j.cclet.2009.06.039

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Silica-bonded S-sulfonic acid (SBSSA) was prepared by the reaction of 3-mercaptopropylsilica (MPS) and chlorosulfonic acidin chloroform.This solid acid has been employed as a recyclable catalyst for the synthesis of coumarins from phenols and β-ketoesters at 80 ℃ under solvent-free conditions.

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Synthesis and mesomorphic behavior of benzothiazole-based liquid crystals having terminal methoxyl group

Sie Tiong Ha, Teck Ming Koh, Siew Teng Ong, Yasodha Sivasothy

中国化学快报. 2009, 20(12): 1449-1452. https://doi.org/10.1016/j.cclet.2009.06.023

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A homologous series of benzothiazole derivatives, 6-methoxy-2-(4-alkanoyloxybenzylidenamino)benzothiazoles, were synthesized and characterized using FT-IR, ¹H and ¹³C NMR, mass spectrometry and elemental analysis.Enantiotropic nematic phase was observed throughout the entire series.Smectic C phase only emerged from the decanoyloxy derivative onwards.The terminal methoxyl group and the ester linkage influenced the mesomorphic behavior of the present series.

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Boric acid as an efficient catalyst for the synthesis of 1,1-diacetate under solvent-free condition

K.F.Shelke, S.B.Sapkal, G.K.Kakade, P.V.Shinde, B.B.Shingate, M.S.Shingare

中国化学快报. 2009, 20(12): 1453-1456. https://doi.org/10.1016/j.cclet.2009.07.009

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Boric acid (BO₃H₃) is an inexpensive, efficient and mild catalyst for the synthesis of 1,1-diacetate (acylal) from the various aromatic and heteroaryl aldehydes with acetic anhydride at room temperature under solvent-free condition.The present method does not involve any hazardous organic solvents or catalysts.This method gives notable advantages such as excellent chemoselectivity,mild reaction condition, short reaction times and excellent yield.

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Silica sulfuric acid:A versatile reagent for oxathioacetalyzation ofcarbonyl compounds and deprotection of 1,3-oxathiolanes

Farhad Shirini Parisa Sadeghzadeh, Masoumeh Abedini

中国化学快报. 2009, 20(12): 1457-1460. https://doi.org/10.1016/j.cclet.2009.07.006

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Oxathioacetalyzation of carbonyl compounds with 2-mercaptoethanol and deprotection of the obtained 1,3-oxathiolanes is easily performed in the presence of silica sulfuric acid (SSA).All reactions were performed under mild and completely heterogeneous reaction conditions in good to high yields.

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Synthesis of tanshinone ⅡA analogues and their inhibitory activities against Cdc25 phosphatases

Wei Gang Huang, Jing Ya Li, Yu Luo, Jia Li, Wei Lu

中国化学快报. 2009, 20(12): 1461-1464. https://doi.org/10.1016/j.cclet.2009.07.008

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Two series of tanshinone ⅡA derivatives were synthesized and evaluated for their antitumor activities as Cdc25 phosphatase inhibitors.Most of them demonstrated potent Cdc25 inhibitory activity and powerful cytotoxicity against A549 tumor cell line,producing IC₅₀ values in very low micromolar range.At last, the preliminary SAR was discussed.

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Prenylated flavonoids from Tephrosia apollinea

Ali K.Khalafallah, Suleiman A.Suleiman, Afifi H.Yousef, Nadia A.A.El-kanzi, Abou El-Hamd H.Mohamed

中国化学快报. 2009, 20(12): 1465-1468. https://doi.org/10.1016/j.cclet.2009.05.025

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In continuation of our chemical investigation on some medicinal plants of the genus Tephrosia, re-investigation of the methylenechloride/methanol (1:1) extract of the air-dried aerial part of Tephrosia apollinea afforded a new prenylated flavonoid 1,in addition to an aromatic ester, a sesquiterpene, a lignan and several known prenylated flavonoids.The structures were established by (¹H NMR,¹³C NMR, DEPT,¹H-¹H COSY, HMQC, HMBC, NOESY and HRMS).Relative configurations of 9 and 10 wereconfirmed by X-ray analysis.

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Two new prenylflavonoids from Morus nigra L.

Lei Wang, Ting Gong, Ruo Yun Chen

中国化学快报. 2009, 20(12): 1469-1471. https://doi.org/10.1016/j.cclet.2009.06.035

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Two new prenylflavonoids, mornigrol E(1) and mornigrol F(2) were isolated from Morus nigra L.Their structures were elucidated on the basis of spectroscopic methods, especially 2D-NMR techniques.

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A new sesquiterpene from the roots of Vladimiria souliei

Jing Xu, Xiao Jun Zhao, Yuan Qiang Guo, Wen Bin Hou, Shu Zhong Zhang

中国化学快报. 2009, 20(12): 1472-1474. https://doi.org/10.1016/j.cclet.2009.07.014

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A new sesquiterpene, named vladimenal (1), was isolated from the roots of Vladimiria souliei.The structure was elucidated on the basis of spectroscopic analysis.

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Aptameric SERS sensor for Hg²⁺analysis using silver nanoparticles

Guo Qing Wang, Ling Xin Chen

中国化学快报. 2009, 20(12): 1475-1477. https://doi.org/10.1016/j.cclet.2009.06.029

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Aptamer-silver nanoparticles (AgNPs) based surface-enhanced Raman scattering (SERS) sensor has been developed for Hg²⁺detection by employing the structure-switching aptamer in the presence of spermine.This simple method shows excellent sensitivity and selectivity owing to the sensitive SERS detection technique and high specificity of aptamer for binding Hg²⁺.

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Study on the influence of humic acid of different molecular weight on basic ion exchange resin's adsorption capacity

Jin Nan Wang, Ai Min Li Yang Zhou, Li Xu

中国化学快报. 2009, 20(12): 1478-1482. https://doi.org/10.1016/j.cclet.2009.07.013

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In this paper, humic acid (HA) was ultra-filtered into different molecular weight sections and was characterized by multielementanalysis, UV₂₅₄/TOC, FT-IR and three-dimensional fluorescence spectrometric.Since humic acids of different molecular weights have different hydrophilic and molecular size, the maximum adsorption capacity of basic ion exchange resins appears on the humic acid whose molecular weight ranges from 6000 to 10,000 Da.

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Simultaneous determination of fluorine and iodine in urine by ion chromatography with electrochemical pretreatment

Kang Kang Hu, Wei Xiong Huang, Yu Hua Su, Rong Zong Hu

中国化学快报. 2009, 20(12): 1483-1486. https://doi.org/10.1016/j.cclet.2009.05.030

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A new method for the simultaneous determination of fluorine and iodine in urine by ion chromatography (IC) with electrochemical pretreatment has been developed.The pretreatment was performed in a novel electrochemical oxidation-neutralization device (EOND), in which iodide of the sample was oxidized to iodate and the alkaline digestion sample solution was neutralized.Under the optimized conditions, the limits of detection (LOD, S/N=3) were 2.5 μg/L for fluoride and 20 μg/L for iodate, respectively.The recoveries were in the range of 93-102% for fluoride and 86-98% for iodate.

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Short communication Refolding of reduced/denatured bovine pancreatic insulin with ion-exchange chromatography coupled with MALDI-TOF MS

Cui E.Lin, Quan Bai

中国化学快报. 2009, 20(12): 1487-1490. https://doi.org/10.1016/j.cclet.2009.07.005

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The refolding of the reduced/denatured insulin from bovine pancreas as the model protein was investigated with weak anionexchange chromatography (WAX) coupled with MALDI-TOF MS.The results indicated that the disulfide bonds almost cannot be formed correctly with the common mobile phase by WAX.However, with the urea gradient elution and in the presence of GSSG/ Cyst as the ratio 1:6 in the mobile phase employed, the disulfide exchange of reduced/denatured insulin can be accelerated resulting in forming the correct three disulfide bonds.The protein refolding efficiency of reduced/denatured insulin can be increased from 3% to 34%.The effects of urea gradient and the oxidant and reductant groups, such as GSSG/GSH, Cyst, and GSSG/Cyst, on the forming the disulfide bonds of reduced/denatured insulin were investigated in detail.The results were further tested by the separation of the WAX fraction of reduced/denatured insulin with RPLC and MALDI-TOF MS.

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Use of packed-fiber solid-phase extraction for sample clean-up and preconcentration of vitamin B ₁₂ before determination

Fang Fang, Xue Jun Kang, Zhi Yong Liu, Yu Qin Ma, Zhong Ze Gu

中国化学快报. 2009, 20(12): 1491-1494. https://doi.org/10.1016/j.cclet.2009.06.030

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A rapid and simple preconcentration step applying packed-fiber solid-phase extraction columns has been investigated to vitamin B 12.The extraction performance of the new method was investigated preliminarily on vitamin functional drink.The analysis used a reversed-phase C₁₈ column, with a photo-diode array detector at 220 nm.The samples were preconcentrated with packed-fiber solid-phase extraction columns.Good linearity was observed in vitamin functional drink.The repeatability of extraction performance, expressed as relative standard deviations, was from 3.5% to 4.3%.The limit of detection (LOD) is 5 ng mL^-1(S/N=3).Finally, the method had been applied for the determination of vitamin B 12 in vitamin functional drink.

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New matrix of MALDI-TOF MS for analysis of small molecules

Shu Zhang, Yi Chen, Jian An Liu, Shao Xiang Xiong, Guang Hui Wang, Jun Chen, Guo Qiang Yang

中国化学快报. 2009, 20(12): 1495-1497. https://doi.org/10.1016/j.cclet.2009.06.031

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New matrix, metal-phthalocyanine (MPc), of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) was used for analysis of small molecules (usually < 500 Da).By using MPcs as matrices, small molecular samples were moved to high mass-to-charge region where there was no interference caused by the traditional matrices.The mass of the target analyte was obtained by simple calculation.

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Determination of inorganic anions in ethyl acetate by in-line hollow fiber membrane extraction with ion chromatography

Zhen Zhen Hu, Ying Ying Zhong, Yun Chang Fan, Yan Zhu

中国化学快报. 2009, 20(12): 1498-1501. https://doi.org/10.1016/j.cclet.2009.07.016

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In this work, a novel hollow fiber membrane extractor was set up to extract inorganic anions from ethyl acetate using deionized water.Inorganic anions in slightly soluble organic solvents can be determined by the in-line hollow fiber membrane extractor coupled with ion chromatography at first time.Different aspects of the extraction procedure such as magnetic stirring speed,extraction flow rate and extraction time were optimized to achieve high extraction efficiency and good separation results.Satisfactory linear range, limits of detection and good repeatability were obtained.The procedure was applied to analyze inorganic anions in two commercial ethyl acetate samples.

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Synthesis of novel biodegradable poly(ethylene glycol) analogue:Water-soluble aliphatic polyester with pendant oligo(ethylene glycol) chains

Lei Feng, Jian Yuan Hao, Cheng Dong Xiong, Xian Mo Deng

中国化学快报. 2009, 20(12): 1502-1505. https://doi.org/10.1016/j.cclet.2009.06.013

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A novel poly(ethylene glycol) (PEG) analogue composed of aliphatic polyester backbone and pendant oligo(ethylene glycol) short chains is reported.The PEG analogue is a copolymer synthesized by ring-opening alternating copolymerization of succinicanhydride with 2-((2-(2-metho xyethoxy)ethoxy)methyl)oxirane.The structure of the copolymer was confirmed by ¹H NMRspectrum.The effects of the monomer feed ratio on the copolymerization were studied and the polymerization mechanism was given.The PEG analogue disclosed is water-soluble and expected to have promising applications in biomedical fields as a substitute of PEG due to the existence of degradable ester bond in the backbone.

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Different crystallinity of poly(d,l-lactide-co-p-dioxanone) copolymers acquired by control of chain microstructure

Hui Zhen Zhao, Jian Yuan Hao, Cheng Dong Xiong, Xian Mo Deng

中国化学快报. 2009, 20(12): 1506-1509. https://doi.org/10.1016/j.cclet.2009.07.012

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Poly(d,l-lactide-co-p-dioxanone) (P(LA-co-PDO)) copolymers with different chain microstructures were synthesized by onestep or two-step bulk ring-opening polymerizations of d,l-lactide (LA) and p-dioxanone (PDO) monomers using stannous octoate [Sn(Oct)₂ ]/n-dodecanol as the initiating system.The average sequence lengths of the lactidyl (L_LA) and dioxanyl (L_PDO) units were calculated from the ¹H NMR spectra.It was found that both L_LA and L_PDO values from the two-step syntheses were significantly longer than those from the corresponding one-step syntheses, indicating more blocky structure achieved for the twostep copolymers.Corresponding to this difference in microstructure, the two-step copolymers were semi-crystalline, while the one-step copolymers were completely amorphous.In conclusion, the crystallinity of P(LA-co-PDO) copolymers could be adjusted conveniently to meet specific applications by changing the microstructure of the copolymers via different polymerization routes.

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Synthesis and properties of novel thermotropic liquid crystalline copoly(ester-imide)s

Guo Yao, Yi Gu

中国化学快报. 2009, 20(12): 1510-1513. https://doi.org/10.1016/j.cclet.2009.07.004

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Four novel copoly(ester-imide)s based on 3,3',4,4'-biphenyltetracarboxylic dianhydride, bis(trimellitic acid anhydride) phenyl ester and di-p-aminophenyl ester of dicarboxylic acids were synthesized via two-step method in order to investigate whether two imide mesogenic units with different conformation and polarity could control the formation of LC-phase.Polarizes light microscopy (PLM) and differential scanning calorimetry (DSC) have shown that three polymers formed the nematic phase with "thread schlieren texture" and a polymer formed the nematic phase with "Inversion walls texture".

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Synthesis and characterization of α-butyl-ω-{3-[(2,2-dihydroxymethyl)-propionyloxy]}propylpolydimethylsiloxanes

Meng Zhang, Jun Ying Li, Guo Wei Zhou, Yuan Juan Wu, Yong Mei Xia, Tian Duo Li

中国化学快报. 2009, 20(12): 1514-1517. https://doi.org/10.1016/j.cclet.2009.06.027

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A series of polydimethylsiloxanes containing two primary hydroxyl groups at one single chain end were synthesized by five-step reactions which included esterification, hydroxyl protection, anionic ring-opening polymerization, hydrosilylation and deprotection.The prepared compounds in each step were characterized.The results showed that each step synthesis was successfully carried out and objective products could be achieved.

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2009年, 第20卷, 第12期　刊出日期：2009-12-20

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2009年, 第20卷, 第12期 刊出日期：2009-12-20

2009年, 第20卷, 第12期　刊出日期：2009-12-20