Chinese Journal of Chemistry

Cover image for Chinese Journal of Chemistry

January, 2009

Volume 27, Issue 1

Pages 13–208

  1. Preface

    1. Top of page
    2. Preface
    3. Editorial
    4. Communications
    5. Full Papers
    6. Notes
    1. Preface – Professor Qingyun Chen

      Jichang XIAO

      Article first published online: 17 FEB 2009 | DOI: 10.1002/cjoc.200990035

  2. Editorial

    1. Top of page
    2. Preface
    3. Editorial
    4. Communications
    5. Full Papers
    6. Notes
    1. Editorial

      Editor-in-Chief Guozhen JI and Deputy Associate Editor-in-Chief Shengming MA

      Article first published online: 10 FEB 2009 | DOI: 10.1002/cjoc.200990034

  3. Communications

    1. Top of page
    2. Preface
    3. Editorial
    4. Communications
    5. Full Papers
    6. Notes
    1. Synthesis and Absolute Configuration of the Diynediol from Psathyrella scobinacea (pages 13–15)

      Jianzhong WU, Yikang WU, Yajun JIAN and Yihua ZHANG

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990005

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      All the four isomers of Scobidiynediol (hepta-4,6-diyne-2,3- diol), a natural product isolated from white-rot fungus Psathyrella scobinacea, were synthesized using either (R)- or (S)-lactate as the source of chirality. The relative configurations of the diols were established by NOE experiments performed on the cyclic acetonides. The relative as well as absolute configurations of the natural Scobidiynediol was assigned as (2S,3S) through comparison of the optical rotation and 1H NMR data.

    2. Synthesis of Tonghaosu Analogues (pages 16–18)

      Hai SUN, Yingjie LIN, Yulin WU and Yikang WU

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990010

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      Several new analogues of natural antifeedant tonghaosu were synthesized via m-CPBA oxidation of corresponding 3-(α-furyl)propanols, Luche reduction of the resulting enone, epoxidation, acid-mediated spiroketalization, and radical mediated dehydration.

    3. An Efficient Guanylation of Aromatic Amines Catalyzed by Samarium Diiodide (pages 19–22)

      Xuehua ZHU, Fan XU and Qi SHEN

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990017

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      An efficient guanylation of aromatic amine with carbodiimide in the presence of a catalytic amount of samarium diiodide was developed. The reaction was carried out under mild conditions giving a variety of guanidines in good to excellent yields.

    4. Automatic Identification of Antibodies in the Protein Data Bank (pages 23–28)

      Xun LI and Renxiao WANG

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990021

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      An automatic method has been developed for identifying antibody entries in the Protein Data Bank (PDB). Our method, called KIAb (Keyword-based Identification of Antibodies), parses PDB-format files to search for particular keywords relevant to antibodies, and makes judgment accordingly. Our method identified 780 entries as antibodies on the entire PDB. Among them, 767 entries were confirmed by manual inspection, indicating a high success rate of 98.3%. Our method recovered basically all of the entries compiled in the Summary of Antibody Crystal Structures (SACS) database. It also identified a number of entries missed by SACS. Our method thus provides a more complete mining of antibody entries in PDB with a very low false positive rate.

  4. Full Papers

    1. Top of page
    2. Preface
    3. Editorial
    4. Communications
    5. Full Papers
    6. Notes
    1. Chiral Separation of Calcium (−)-2(S)-2-Benzyl-4-oxo-4-(cis-hexahydro-2-isoindolinyl)butyrate Enantiomers by High-performance Liquid Chromatography (pages 29–32)

      Zhefeng ZHANG, Gengliang YANG, Wenhui GAO and Yi CHEN

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990022

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      A chiral high-performance liquid chromatographic method was developed for the enantioseparation of a new insulinotropic drug of the glinide class with rapid onset. The chiral separation was performed on a Sumichiral OA-3300 column (250 mm×4.6 mm, 5 µm) with methanol containing 0.05 mol/L ammonium acetate as the optimized mobile phase at detection wavelength 210 nm. Baseline separation of the two enantiomers was obtained in 22 min with a resolution of 3.01. Calibration graphs were constructed in a range of 0.028–5.6 µg·mL−1 for S- and 0.03–6.0 µg·mL−1 for R-(−)-enantiomer, respectively.

    2. Synthesis, QSAR Study and Optimization of Propiophenone Oxime Derivatives (pages 33–42)

      Liang CHEN, Ying HUANG, Wei XIE, Jin CAO, Changchun NI, Zhou SHEN, Xiuli LI, Yibin ZHANG, Tianxiang SHEN, Fei YU, Bin LIU, Liping YUAN and Jianhua YAO

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990023

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      Two lead compounds were designed based on the CoMFA and CoMSIA models constructed by experimental data. Their predicted and observed bioactivities are corresponding.

    3. Selective Colorimetric Fluoride Sensor: A Heteroditopic Receptor Combining Pyrrolic Amide with Urea (pages 43–48)

      Zhenming YIN and Shangyuan LIU

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990024

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      A heteroditopic anion receptor has been synthesized. Naked-eye detectable color change, from colorless to yellow, of the receptor solution took place only when fluoride was added.

    4. Theoretical Studies on the Reaction Mechanisms of C3H2 (cyclopropenylidene) and O(3P) Radicals (pages 49–55)

      Xiaohua XIE, Wei SHEN, Rongxing HE, Jinsheng ZHANG and Ming LI

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990025

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      The complex potential energy surface for the reaction of C3H2 (cyclopropenylidene) with O(3P) was explored computationally using a density functional and ab initio QCISD(T) methods. The geometries of all the stationary points were fully optimized at the B3LYP/6-311++G∗∗ computational level, and the single point calculation including full population analysis was performed by employing QCISD(T).

    5. Pt and Pt-Ru Nanoparticles Dispersed on Ethylenediamine Grafted Carbon Nanotubes as New Electrocatalysts: Preparation and Electrocatalytic Properties for Ethanol Electrooxidation (pages 56–62)

      Xinxian ZHONG, Xiaohua ZHANG, Xinping SUN, Bo LIU, Yafei KUANG and Jinhua CHEN

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990026

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      In this paper, the ethylenediamine (ED)-grafted multiwalled carbon nanotubes (MWNT) were prepared by a chemical synthesis method, and used as the support of Pt and Pt-Ru catalysts for ethanol electrooxidation. The morphology and elemental composition and the electrocatalytic properties of the resultant Pt-Ru/ED/MWNT and Pt/ED/MWNT catalysts were characterized.

    6. DNA Probe and Cleavage Studies Based on the Interaction between DNA and Yb, Er Complexes of 2-[(Trifluoroaceto)aceto]thinophene-piperidine Ligands (pages 63–68)

      Caixia YIN, Fangjun HUO, Yanbo WU, Yanlin LIU and Pin YANG

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990027

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      Two kinds of [Ln(TTA)4]·HP (Ln=Yb, Er) all can cleavage circular plasmid pBR322 DNA into OC form rather than linear form at pH=7.2 and 37 °C and the mechanism may be hydrolytic cleavage.

    7. Synthesis, Crystal Structure and Photoluminescent Properties of Two Novel Two-dimensional Coordination Networks Assembled by Lanthanide Salts and Carboxylate Ligand (pages 69–73)

      Yajuan LI, Huihua SONG, Qing LIANG, Rong HE and Zhen WEI

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990028

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      Two novel lanthanide coordination polymers [Ln(PDC)(OH)(H2O)2]n (Ln=Eu (1) and Tb(2), H2PDC=pyridine-3,4-dicarboxylic acid) have been synthesized and characterized by elemental analysis, IR, TGA and single-crystal X-ray diffraction. Their luminescent properties have been also investigated.

    8. Xanthones from the Bark of Garcinia xanthochymus and Their 1,1-Diphenyl-2-picrylhydrazyl Radical-Scavenging Activity (pages 74–80)

      Fangfang ZHONG, Yu CHEN, Ping WANG, Huijin FENG and Guangzhong YANG

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990029

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    9. Theoretical Study on Mechanism of Hydroformylation of Ethene Catalyzed by a Heterobimetallic Rh(I)-Cr Complex (pages 81–87)

      Dianyong TANG, Yuanqin ZHANG and Changwei HU

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990030

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      Both the associative and dissociative mechanisms of ethene hydroformylation catalyzed by a heterobimetallic complex HRh(CO)(PH3)(µ-PH2)2Cr(CO)4 were investigated by density functional theory, finding that the introduction of Cr(CO)4 moiety does not remodel the mechanism of hydroformylation of simple alkenes, and the dissociative mechanism is predominant with the carbonyl insertion as a rate-limiting step.

    10. Photocatalytic Degradation of Dicofol and Pyrethrum with Boric and Cerous Co-doped TiO2 under Light Irradiation (pages 88–92)

      Lifen GONG, Jing ZOU, Jinbin ZENG, Wenfeng CHEN, Xi CHEN and Xiaoru WANG

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990031

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      Boric and cerous co-doped nano titanium dioxide (B/Ce co-doped TiO2) was synthesized using a sol-gel technique, which involved the hydrolyzation of tetrabutyl titanate with the addition of boric acid and cerous nitrate. The B/Ce co-doped TiO2 was employed for the photocatalytic degradation of dicofol, cyfluthrin and fenvalerate under light irradiation. XRD, TEM, FT-IR and UV-Vis DRS methods were used to characterize the crystalline structure. Experimental results showed that only the anatase signal phase was found for B/Ce co-doped TiO2, but multiplicate phases, including anatase, rutile and less brookite phases, were identified both in the pure TiO2 nanoparticles and Ce-doped TiO2 nanoparticles.

    11. Salicylate-selective Potential Response of an Electrode Based on a Copper(II)-phthalocyanine Derivative as an Ionophore (pages 99–104)

      Wenju XU, Ruo YUAN and Yaqin CHAI

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990033

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      The PVC membrane electrode based on 2,9,16,23-copper(II)-tetranitrophthalocyanine (Cu(II)TNPc) as the sensing carrier exhibited the preferential potential response to salicylate (Sal), which may be suggested to originate from the axial coordination interaction of salicylate anion with the central metal of the carrier.

    12. A Novel MALDI Matrix for Analyzing Peptides and Proteins: Paraffin Wax Immobilized Matrix (pages 105–110)

      Yuanlong WEI, Yuan MEI, Zhe XU, Cuihong WANG, Yinlong GUO, Yiping DU and Weibing ZHANG

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990000

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      2,5-Dihydrobenzoic acid (DHB) was deposited on the hot paraffin wax layer to produce paraffin wax immobilized matrices, which were used to study peptide mixtures and proteins. The MALDI-FTMS analysis results showed that the detection sensitivity of matrices immobilized in the paraffin sample support was better than that on other sample supports.

    13. Probing the Subunit-Subunit Interaction of the Tetramer of E. coli KDO8P Synthase by Electrospray Ionization Mass Spectrometry (pages 111–116)

      Zhili LI and Apurba Kumar SAU

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990001

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      The effect of ligands on the overall structure of enzyme in different bound states was examined using electrospray ionization mass spectrometry. The data indicate that this method is a powerful tool in probing the subtle conformational changes of the multiprotein assemblies upon ligand binding.

    14. Dynamic Covalent Self-Assembly of Mono-, Bi- and Trimacrocycles from Hydrogen Bonded Preorganized Templates (pages 117–122)

      Jianbin LIN, Jing WU, Xikui JIANG and Zhanting LI

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990002

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    15. ESI-FTICRMS Characterization of the Intermediates in Cycloisomerization of Trifluoromethyl-substituted Enynols through Changing the Protecting Group of Substrate (pages 123–129)

      Rong QIAN, Yinlong GUO and Long LÜ

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990003

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      Two assumed reaction intermediates of cycloisomerization of trifluoromethyl-substituted enynols were characterized by ESI-FTICRMS through changing the protecting groups of substrates.

    16. Synthesis and Complexation Studies of Calix[4]crown Telomers Intermolecularly Bridged with Calixarene Segments (pages 130–134)

      Haibing LI, Demei TIAN, Yuanyin CHEN and Zhinong GAO

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990004

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      Three derivatived calix[4]crowns were condensed with 2,6-bis(bromomethyl)-4-methylanisole (BBA) to afford their telomers TCA[4]. The binding sites may complex metal ions or amino acids selectively. The telomers shows different metal ions selectivity in comparison with their monomers.

    17. Stereoselective Synthesis of the Functionalized C2–C10 Fragment of Clavulactone (pages 135–140)

      Zuozhong ZHOU, Dong SUO, Zhenyu YANG, Lin CHEN, Taishan HU and Zhujun YAO

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990006

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      A stereoselective synthesis of all functionalized C2–C10 fragment 13 of the antitumor marine natural product clavulactone was accomplished in 15 steps and 5% overall yield, starting from readily available materials. Fragment 13 contains all preset functionalities and will be a useful precursor for the convergent total synthesis of clavulactone.

    18. Metal-mediated gem-Difluoroallylation of N-Acylhydrazones: Highly Efficient Synthesis of α,α-Difluorohomoallylic Amines (pages 141–150)

      Xuyi YUE, Xiaolong QIU and Fengling QING

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990007

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      Indium-mediated gem-difluoroallylation of aldehyde-derived N-acylhydrazones 1a1q with 3-bromo-3,3-difluoropropene 2 afforded α,α-difluorohomoallylic hydrazides 3a3q in high yields. By means of substitution of Zn powder for indium, gem-difluoroallylation of ketone-derived N-acylhydrazones 6a6d also provided the corresponding α,α-difluorohomoallylic hydrazides 7a7d in medium yields.

    19. Enantioselective Fluorescent Sensor Based on Calix[4]arene and S-Binol for the Recognition of N-Boc-glutamate (pages 157–162)

      Chenguang HU, Xiaohuan HUANG, Zhihong CHEN and Yongbing HE

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990009

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    20. Asymmetric Conjugate Addition of Unmodified Cyclic Ketones to Nitroolefins Using Aminophosphonate as the Organocatalyst (pages 163–168)

      Gang CHEN, Zheng WANG and Kuiling DING

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990011

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      ?n enantiopure α-aminophosphonate has been synthesized and was found to be effective as a chiral organocatalyst for the asymmetric conjugate addition of cycloketones to β-nitrostyrenes. With a catalyst loading of 20 mol% and in the presence of 10 mol% of CF3COOH as a cocatalyst, the Michael adducts could be obtained with varying degrees of diastereo- and enantioselectivities (up to 97:3 and 90% ee respectively) under solvent-free conditions.

    21. KF-Montmorillonite-catalyzed Michael Addition Reaction of Malononitrile to α,β-Unsaturated Ketones (pages 169–173)

      Daqing SHI, Nan WU and Qiya ZHUANG

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990012

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      The Michael addition reaction of α,β-unsaturated ketones with malononitrile catalyzed by KF-montmorillonite was investigated. It was interesting to note that at different reaction temperatures the addition and cycloaddition reaction products were obtained. This method has the advantages of good yields, mild reaction conditions, easy work-up and inexpensive reagents over the existing procedures.

    22. Improvement of Hydrophobicity of Ionic Liquids by Partial Chlorination and Fluorination of the Cation (pages 174–178)

      Kuilong TAN, Chunxi LI, Hong MENG and Zihao WANG

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990013

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      Two novel hydrophobic ionic liquids (IL) with partial substitution of chlorine and fluorine in the 1-butyl-3-methylimidazolium cation (noted as [BMIM] or [C8H15N2], viz. [C8H12.28Cl0.96F1.76N2]Cl and [C8H12.75Cl1.58F0.67N2][PF6]), were reported in this paper, which were prepared from the precursors [BMIM]Cl and [BMIM][PF6], respectively through chlorination with chlorine gas and fluorination with potassium fluoride. The position of the chlorine substitution in the resulting IL was identified using proton nuclear magnetic resonance (1H NMR).

    23. Stereocontrolled Synthesis of (E)-β,γ-Unsaturated Esters via Palladium-Catalyzed Cross-Coupling of (E)-Alkenylboronic Acids with α -Bromoacetic Esters (pages 179–182)

      Yazhen DUAN, Jianshe ZHANG, Jun YANG and Minzhi DENG

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990014

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      The cross-coupling reaction of trans-alkenylboronic acids with ???α????-bromoacetic esters was firstly studied. It was found that using Pd(OAc)2 as catalyst, a bulky electron-rich phospine, (2-dicyclohexylphospino-biphenyl) as ligand, the reaction can be readily accomplished to give specific (E)-???β???????? γ????-unsaturated esters in high yields.

    24. A Concise Synthesis of (−)-Indolizidines 209D and 209B (pages 183–188)

      Hao WU, Menglong YU, Yazhu ZHANG and Gang ZHAO

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990015

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      (−)-Indolizidine 209D and 209B were efficiently synthesized in very short steps using readily available L-proline as starting material. The key feature of the approach resides in the addition reaction of ethyl lithiopropiolate to the key intermediates aldehyde 3 or ketone 10.

    25. Facile Synthesis of Monofluoro γ -Lactones and Pyrrolidine Derivatives via Electrophilic Fluorination of Allenoic Acids and Amides (pages 189–194)

      Haifeng CUI, Zhuo CHAI, Gang ZHAO and Shizheng ZHU

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990016

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      A convenient method to synthesize a series of monofluoro γ-lactones and pyrrolidine derivatives in moderate to good yields via the electrophilic fluorination of γ-allenoic acids and tosylamides using Selectfluor was developed.

    26. Synthesis of Small Peptides and Their Use as Bifunctional Chelating Agents in Diagnostic Radiopharmaceuticals (pages 195–201)

      Chongzhi TANG, Longjin LI, Zhen PANG and Zhibin YUAN

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990018

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      Three linear mercaptoacetyl tetrapeptides, MAG3-Leu-OH, MAG3-Phe-OH and MAG3-Tyr-OH, were synthesized via a liquid phase synthetic approach with high yields and high purities without using preparative HPLC technique. The obtained products could be radiolabeled easily with 99mTc under a mild condition and showed high stability in vitro and in vivo conditions. The scintigrams of the tested rabbit after injection of the radiolabeled products via mainline showed a normal biodistribution, which is definitely different from that of 99mTc-MAG3, indicating different routes of metabolization between these two radiochemicals.

  5. Notes

    1. Top of page
    2. Preface
    3. Editorial
    4. Communications
    5. Full Papers
    6. Notes
    1. An Efficient Method for the Preparation of Pentafluoroiodoethane from Chloropentafluoroethane (pages 202–204)

      Chengpan ZHANG, Jinhong LIN, Zhenwei QIANG and Jichang XIAO

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990019

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      An efficient method was developed for the synthesis of pentafluoroiodoethane from chloropentafluoroethane. Sulfinatodechlorination of CF3CF2Cl was carefully investigated. Subsequent iodination can be conducted in one pot without further purification, giving the corresponding CF3CF2I in practically acceptable yield.

    2. Versatile Chiral Building Blocks from D-Xylose (pages 205–208)

      Zhibin ZHEN, Jian GAO and Yikang WU

      Article first published online: 20 JAN 2009 | DOI: 10.1002/cjoc.200990020

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