中国化学快报

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First total synthesis of (±)-puyanin and (±)-4'-O-methylbonannione

Jin Hui Yang, Yu Heng Zhang, Hong Jun Li, Shi Zhi Jiang, Yun Feng Li

中国化学快报. 2010, 21(11): 1267-1269. https://doi.org/10.1016/j.cclet.2010.06.037

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A facile approach for the first total synthesis of two naturally occurring geranylated flavonoids, (±)-puyanin 1 and (±)-4'-O-methylbonannione 2 has been obtained with total yield 27% and 21%, respectively. The key steps were regioseleetive cyclization of geranylated trihydroxychalcone and regioselective geranylation of 2, 4, 6-trihydroxyacetophenone.

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A new and convenient synthesis of phendiones oxidated by KBrO₃/H₂SO₄ at room temperature

Ren Hua Zheng, Hai Chang Guo, Hua Jiang Jiang, Ke Hui Xu, Bei Bei Liu, Wei Lin Sun, Zhi Quan Shen

中国化学快报. 2010, 21(11): 1270-1272. https://doi.org/10.1016/j.cclet.2010.05.030

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A new method is described to synthesize phendione derivatives from 1, 10-phenanthrolines using potassium bromate and 60%sulfuric acid as oxidant, which was easily applicable to scale-up. The reaction conditions are mild and the yields are excellent. The target compounds have been characterized by ¹H NMR, and IR.

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Synthesis of novel D-seco-taxoids derived from 1-deoxybaccatin Ⅵ

Jun Chao Shao, Zhi Hua Ye, Hai Xia Lin, Dian Long Wang, Na Han

中国化学快报. 2010, 21(11): 1273-1276. https://doi.org/10.1016/j.cclet.2010.07.001

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New D-seco-taxoids were synthesized from 1-deoxybaccatin Ⅵ and their structures were confirmed by ¹H NMR, ¹³C NMR, ESIMS and X-ray crystallography. The key step of the synthesis involved the opening of the oxetane ring under acid and basic conditions in order to obtain new multidrug resistance (MDR) reversal agents and new synthetic precursors of paclitaxel analogues.

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Convenient synthesis of chiral H₄-BINOL via direct hydrogenation of BINOL

Qian Chang Ding, Yun Feng Du, Xin Sheng Li, Dong Cheng Xu

中国化学快报. 2010, 21(11): 1277-1280. https://doi.org/10.1016/j.cclet.2010.07.013

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A simple, highly effective hydrogenation of chiral BINOL to provide H₄-BINOL in multigram scale with good yield (up to 78% yield) was developed. A series of heterogeneous catalysts was tested in the hydrogenation; the best result was obtained with 5% Pd/C in EtOH under the H₂ pressure of 50 bar for 2 h. This method is a more useful method for practical synthesis of optically pure H₄-BINOL than other available methods.

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The new shortcut synthesis of 8-oxocoptisine

Xiang Juan Cui, Ying Ying Lu, Min Zhao, Shan Qian, Yong Wu

中国化学快报. 2010, 21(11): 1281-1282. https://doi.org/10.1016/j.cclet.2010.05.019

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8-Oxocoptisine 1, a natural protoberberine alkaloid, can be more easily achieved starting from readily available and inexpensive berberine hydrochlorate 2. The structure of the target compound 1 was confirmed by melting point, ¹H NMR, IR, MS and elemental analysis.

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Selective nitration of phenols using bismuth subnitrate/charcoal in the presence of trichloroisocyanuric acid under aprotic conditions

Ali Reza Pourali, Fatemeh Fatemi

中国化学快报. 2010, 21(11): 1283-1286. https://doi.org/10.1016/j.cclet.2010.05.016

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A mild, efficient and regioselective method for the mononitration of phenolic compounds is described using bismuth subnitrate/charcoal in the presence of trichloroisocyanuric acid in CH₂Cl₂ at room temperature.

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An expeditious synthesis of isoxazoline using cetyltrimethylammonium cerium nitrate:A phase transferring oxidative 1,3-dipolar cycloaddition

Parvin Kumar, Ashwani Kumar

中国化学快报. 2010, 21(11): 1287-1290. https://doi.org/10.1016/j.cclet.2010.05.015

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An expeditious and effective method for synthesis of isoxazoline from aldoximes and activated alkenes using cetyltrimethy-lammonium cerium nitrate at room temperature is described. Reaction was completed within short time period in high yields at room temperature.

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A new method for the synthesis of N-substituted pyrroles

Hai Xue, Tao Ma, Lin Wang, Gang Liu

中国化学快报. 2010, 21(11): 1291-1294. https://doi.org/10.1016/j.cclet.2010.04.030

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An unexpected reaction of 10-bromomethyl-12-oxocalanolide A (2) with primary amine was demonstrated and studied. Consequentially, a new method for the preparation of N-substituted pyrroles starting from γ-halo-α, β-unsaturated ketone was presented.

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Design,synthesis and antitumor activity of a series of novel coumarin-stilbenes hybrids,the 3-arylcoumarins

Chun Fen Xiao, Li Yang Tao, Hong Yi Sun, Wen Wei, Yu Chen, Li Wu Fu, Yong Zou

中国化学快报. 2010, 21(11): 1295-1298. https://doi.org/10.1016/j.cclet.2010.04.034

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A series of novel coumarin-stilbenes hybrids called 3-arylcoumarins were synthesized via Perkin reaction and evaluated as potential antitumor agents. The results showed that some compounds exhibited in vitro activity against KB, KV, MCF-7, MCF-7/ADR cell lines to some extent. Compound 3a showed remarkable effect against KB tumor cells with an IC₅₀ value of 5.18 μmol/L.

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Synthesis and pyrolysis of oligo (methylsilylene)-ethynylene polymer to near-stoichiometric SiC ceramic

Wei Jian Han, Ji Dong Hu, Li Ye, Song Shi, Xue Yu Tao, Tong Zhao

中国化学快报. 2010, 21(11): 1299-1302. https://doi.org/10.1016/j.cclet.2010.06.008

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Oligo (methylsilylene)-ethynylene polymer with erosslinkable ethynyl unit in the main chain was synthesized by condensation of α, ω-dicholorooligo (methylsilane) with dilithioacetylene. The as-synthesized polymer was characterized by GPC, FT-IR and NMR. The results showed ethynyl group was successfully introduced to the polymer main chain. The ceramic yield was dramatically increased by the cross-polymerization of ethynyl group, and the excess silicon of PMS was compensated. Nearstoichiometric (C/Si=1.17) and partial crystallization β-SiC monoliths were obtained by pressureless pyrolysing PSPA at 1200℃in a high yield (73.6 wt%).

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Novel cobalt (Ⅱ) complexes of amino acids-Schiff bases catalyzed aerobic oxidation of various alcohols to ketones and aldehyde

Seyed Mohammad Seyedi, Reza Sandaroos, Gholam Hossein Zohuri

中国化学快报. 2010, 21(11): 1303-1306. https://doi.org/10.1016/j.cclet.2010.06.009

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Two cobalt (Ⅱ) complexes 1 and 2 of Schiff bases derived from amino acids were synthesized and used for oxidation of benzyl alcohol with molecular oxygen at different conditions of pH, solvent, temperature and complex/alcohol molar ratio to optimize reaction conditions and to evaluate the catalytic efficiency of new cobalt Schiff base complexes. Under obtained optimum conditions, various alcohols were oxidized to corresponding aldehydes and ketones.

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First total synthesis of marine alkaloid hyrtiosulawesine

Pu Yong Zhang, Sheng Biao Wan, Su Mei Ren, Tao Jiang

中国化学快报. 2010, 21(11): 1307-1309. https://doi.org/10.1016/j.cclet.2010.05.012

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Hyrtiosulawesine was isolated from Indonesian specimens of the marine sponges Hyrtios erectus and H. reticulatu in 2002. We report here the first total synthesis of hyrtiosulawesine using an efficient and convenient synthetic strategy which could be widely used in the synthesis of other β-carboline compounds. All structures of new compounds were confirmed by ¹H NMR, ¹³C NMR and HRMS.

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Hydrosilylation of olefins over rhodium complex anchored over thioether-functionalized MCM-41

Lig Fang Zha, Wei Sen Yang, Wen Yan Hao, Ming Zhong Cai

中国化学快报. 2010, 21(11): 1310-1313. https://doi.org/10.1016/j.cclet.2010.06.007

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The hydrosilylation of alkenes with triethoxysilane has been achieved at 120℃ in the presence of 0.01 mol% of thioether-functionalized MCM-41 anchored rhodium complex, affording the corresponding addition products in 68-91% yields. This supported rhodium complex can be reused several times without noticeable loss of activity. Our system not only solves the basic problems of catalyst separation and recovery, hat also avoids the use of phosphine ligands.

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Metal-free catalytic reduction of aldehydes,ketones,aldimines,and ketimines

Hiroaki Matsuoka, Kazuhiro Kondo

中国化学快报. 2010, 21(11): 1314-1317. https://doi.org/10.1016/j.cclet.2010.05.029

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The metal-free combination of catalytic amounts of PPh₃, B(C₆F₅)₃, and PhSiH₃ can efficiently hydrosilylate aldehydes, ketones, aldimines and ketimines to afford the corresponding reduction products in good yields.

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Synthesis of 5-substituted benzy 1-2,4-diamino pyrimidine derivatives as c-Fms kinase inhibitors

Li Bao Xu, Wei Sun, Hong Ying Liu, Li Li Wang, Jun Hai Xiao, Xiao Hong Yang, Song Li

中国化学快报. 2010, 21(11): 1318-1321. https://doi.org/10.1016/j.cclet.2010.06.023

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A serials of novel 5-substituted benzyl-2, 4-diamino pyrimidine derivatives have been synthesized and evaluated as inhibitors of c-Fms kinase by the standard MTT method. The results showed that compound 15, 5-[3-methoxy-4-(pyridine-3-yl) benzyl]-2, 4-diamino pyrimidine, had an IC₅₀ of 1.45 μmol/L in inhibiting the proliferation of M-CSF-dependent myeloid leukemia cells in mice (NFS-60), which was similar with GW2580, a selective inhibitor of c-Fms kinase.

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Au/FeO_x-TiO₂ as an efficient catalyst for the selective hydrogenation of phthalic anhydride to phthalide

Ying Xin Liu, Tie Feng Xing, Yi Ming Luo, Xiao Nian Li, Wei Yan

中国化学快报. 2010, 21(11): 1322-1325. https://doi.org/10.1016/j.cclet.2010.06.042

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Au/FeO_x-TiO₂, prepared by deposition-precipitation method, is an efficient and stable catalyst for the liquid phase selective hydrogenation of phthalic anhydride to phthalide under mild reaction conditions.

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Synthesis and in vitro anti-hepatitis B virus activity of 1H-benzimidazol-5-ol derivatives

Dong Chen, Xin Zhai, Qiu Hui Yuan, Jian Luo, Si Chang Xie, Ping Gong

中国化学快报. 2010, 21(11): 1326-1326. https://doi.org/10.1016/j.cclet.2010.05.011

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A series of 1H-benzimidazol-5-ol derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity and eytotoxicity in HepG2.2.15 cells. Half of the tested compounds were found to be potent against HBsAg secretion with IC₅₀ values less than 100 μmol/L. Compounds 14c, 14d, and 14e showed significant inhibitory activity to the viral antigen HBeAg.

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Photo-polymerization of liquid crystalline monomer in oriented liquid crystal phase

Rui Bao, Min Pan, Jin Jun Qiu, He Qing Tang, Cheng Mei Liu

中国化学快报. 2010, 21(11): 1330-1333. https://doi.org/10.1016/j.cclet.2010.05.010

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A new approach to synthesize liquid crystalline polymer with narrow polydispersity index (PDI) was developed. Photo-polymerization of 4-cyanophenyl-4'-(6-acryloyloxyhexyloxy) benzoate(RM23)in nematic liquid crystals with macroscopic orientation was studied. The effects of the monomer concentration on the molecular weight and PDI of the resulting polymers were studied through gel permeation chromatography(GPC)and polarized optical microscopy. The low PDI of 1.19 and 1.22 was obtained in the reverse and normal modes, respectively. The PDI and molecular weight increased with monomer concentration.

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An unexpected Hoffmann elimination during the alkylation of dihydrotetrabenazine

Zhang Yu Yao, Hao Zhang, Huan Ming Sheng, Xiao Ming Wu, Hong Bin Sun

中国化学快报. 2010, 21(11): 1334-1337. https://doi.org/10.1016/j.cclet.2010.06.022

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Dihydrotetrabenazine (DTBZ) is the major pharmacologically active form of tetrabenazine (TBZ), which was approved by FDA for the treatment of chorea associated with Huntington's disease (HD). An unexpected Hoffmann elimination was observed during the treatment of DTBZ with sodium hydrogen and alkyl halides, leading to the formation of both eliminated products (major) and hydroxyl-alkylated products (minor).

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Synthesis of novel analogues of zanamivir as neuraminidase inhibitors

Rui Sheng Xiong, Qing Jie Zhao, Hang Hang Zhu, Zheng Liu, Ya Bing Wei, Jing Shan Shen

中国化学快报. 2010, 21(11): 1338-1341. https://doi.org/10.1016/j.cclet.2010.06.021

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A versatile synthesis of novel zanamivir analogues modified at C-4 and C-8 positions was described. The formation of amides from the acid with corresponding amines, followed by click chemistry generated the triazole substituted compounds as novel analogues of neuraminidase inhibitors in good yields.

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Efficient synthesis of bis (indolyl) methanes catalyzed by (PhCH₂PPh₃)⁺Br₃^- under solvent-free conditions

Farhad Shirini, Mohaddeseh Safarpoor Langroodi, Masoumeh Abedini

中国化学快报. 2010, 21(11): 1342-1345. https://doi.org/10.1016/j.cclet.2010.05.028

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Benzyltripbenylphosphonium tribromide (BTPTB) has been applied as an efficient catalyst for the preparation of bis (indolyl) methanes (BIMs) via electrophilic substitution of indoles with aldehydes in the absence of solvent.

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Wet 2,4,6-trichloro-1,3,5-triazine (TCT) as an efficient catalyst for the synthesis of 2,4,6-triarylpyridines under solvent-free conditions

Behrooz Maleki, Davood Azarifar, Hojat Veisi, Seyede Fatemeh Hojati, Hafezeh Salehabadi, Razieh Nejat Yami

中国化学快报. 2010, 21(11): 1346-1349. https://doi.org/10.1016/j.cclet.2010.06.028

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An efficient one-pot synthesis of 2, 4, 6-triarylpyridines has been described. This involves the three-component reaction of aldehydes, ketones and ammonium acetate in the presence of a catalytic amount of wet 2, 4, 6-trichloro-1, 3, 5-triazine(TCT)under solvent-free condition at 130℃.

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A new flavonoid from the bract of Zea mays L.

Yan Wang, Yin Yan Liu, Xiao Hong Yang, Di Chen, Cheng Peng, Guang Shu Wang

中国化学快报. 2010, 21(11): 1350-1351. https://doi.org/10.1016/j.cclet.2010.06.033

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A new flavonoid was isolated from the bract of Zea mays L. The structure of the compound was identified as 4',5,7-trihydroxy-3',5'-dimethoxyflavone 7-O-[β-D-apiofuranosyl(1→2)]-β-D-glucopyranoside on the ground of chemical and spectroscopic methods.

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A new triterpenoid from Kadsura coccinea

Yan Song, Qing Jie Zhao, Yong Sheng Jin, Chuan Wei Feng, Hai Sheng Chen

中国化学快报. 2010, 21(11): 1352-1354. https://doi.org/10.1016/j.cclet.2010.06.027

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A new triterpenoid, possessing a lanost-9(11)-3-one skeleton, was isolated from the roots of Kadsura coccinea, based on the spectral analysis, its structure was elucidated as 3-hydroxy-12-acetoxycoccinic acid.

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A new nine-membdered lactone from a marine fungus Cladosporium sp.F14

Cheng Hai Gao, Xu Hua Nong, Shu Hua Qi, Xiong Ming Luo, Si Zhang, Hai Rong Xiong

中国化学快报. 2010, 21(11): 1355-1357. https://doi.org/10.1016/j.cclet.2010.06.026

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A new nine-membered lactone, cladospolide E(1), was isolated from a culture broth of a marine fungus Cladosporium sp. F14. The structure of compound 1 was determined on the basis of extensive spectroscopic analysis, including 1D and 2D NMR data.

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Selectivity of guanidinium ionic liquid for capillary gas chromatography

Kai Lu, Li Zhen Qiao, Mei Ling Qi, Ruo Nong Fu

中国化学快报. 2010, 21(11): 1358-1360. https://doi.org/10.1016/j.cclet.2010.04.035

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A guanidinium ionic liquid, N, N, N', N'-tetrabexyl-N", N"-dimethylguanidinium bis (trifluoromethane) sulfonylimide (THDMGNTf₂), was synthesized and used as stationary phase for capillary gas chromatography. In comparison with imidazolium ionic liquid stationary phase, the present new stationary phase exhibits quite different selectivity and behaves more like a low polar stationary phase. The guanidinium ionic liquid of THDMG-NTf₂ exhibited better separation of Grob test mixture than irnidazolium ionic liquid of 1-octyl-3-butylimidazolium bis (trifluoromethane) sulfonylimide (OBIM-NTf₂). Solvation parameter model was also used to evaluate the selectivity of THDMG-NTf₂. Additionally, essential oil of Magnolia biondii Pamp was analyzed to further evaluate the selectivity of THDMG-NTf₂ for a sample of complicated components. Satisfactory separation of the essential oil was achieved on a THDMG-NTf₂ column (10 m) while using a commercial column(30 m)as reference. The present study shows that the guanidinium ionic liquid possesses novel chromatographic selectivity and has great potential for wide applications.

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Development of a competitive format sorbent assay for the determination of parathion in water using molecular imprinted polymer as specific sorbent carrier

Jian She Tang, Li Xiang

中国化学快报. 2010, 21(11): 1361-1365. https://doi.org/10.1016/j.cclet.2010.05.014

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A rapid, simple, and reliable competitive molecular imprinted polymer sorbent assay (MIPSA) was developed and validated for measurement of parathion in water samples. This assay employed a molecular imprinted polymer (MIP) that was synthesized with non-covalent imprinting method as capture reagent and p-aminoparathion conjugate of horseradish peroxidase(para-HRP)as an enzyme label. The assay depended on a competitive binding reaction between the enzyme conjugate and analyte for the binding sites of the MIE The optimized analysis conditions of 10 ng mL^-1 para-HRP and 10 mg mL^-1 polymer were found. The assay was acceptable to detect parathion in water samples under the optimized conditions, with a limit of detection of 50 ng mL^-1. Mean analytical recoveries of added parathion in water samples ranged from 101.2% to 105%. The precision of the assay was satisfactory;relative standard deviation ranged from 4.3% to 6%.

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Oxidative dehydrogenation of ethane to ethene over a superbase supported LiCl system

Yu Bao Zhao, Wen Wen Tan, Hui Li, Xiao Hui Jia, Hui Lin Wan

中国化学快报. 2010, 21(11): 1366-1369. https://doi.org/10.1016/j.cclet.2010.06.025

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LiCl-promoted superbase catalysts were found to be stable and highly selective to ethene for oxidative dehydrogenation of ethane, giving 84% ethane conversion and 74% ethene yield at 923 K. Results indicated that the stronger the basicity of LiCl-based catalysts, the better the catalytic performance.

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Synthesis and characterization of star-comb styrene/butadiene copolymer

Qing Min Zhang, Chuang Chen, Hong Xia Zhang, Chun Qing Zhang, Yang Li, Xi Gao Jian

中国化学快报. 2010, 21(11): 1370-1373. https://doi.org/10.1016/j.cclet.2010.05.013

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A novel star-comb styrene/butadiene copolymer (SC-SBC) was synthesized by anionic polymerization and grafting reaction with epoxidized star liquid polybutadiene (ESPB) as coupling agent. The overall shape of the star-comb macromolecules can be altered by changing the molecular weight and number of the side chain. The molecular parameters and mechanical properties of the SC-SBC resins were investigated. The notched izod impact strength of the SC-SBC resins are excellent and reach as high as to 239 J/m.

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Synthesis and characterization of X-shaped oligo (para-phenylene) derivatives functionalized with fluorene ethynylene

Ke Hong Ding, Xing Ge, Ming Zhang, Si Chun Yuan

中国化学快报. 2010, 21(11): 1374-1377. https://doi.org/10.1016/j.cclet.2010.06.031

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A series of linear and X-shaped oligo (para-phenylene) derivatives functionalized with fluorene ethynylenes 1, 3 and 4 were synthesized through sequent Sonogashira coupling and Suzuki-Miyaura reaction in high yield. The electron-donating group -OCH₃ and electron-withdrawing counterparts -CF₃ were introduced to tune the spectra properties of compounds 3 and 4. The detail investigation of their photophysical properties in solution and film indicated that the introduction of both-OCH₃ and -CF₃ makes maximum emission distinct red-shift in comparison with parent compound 1, but the latter more prominently.

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Potentiometric detection of polyions based on functionalized magnetic nanoparticles

De An Song, Rong Ning Liang, Rui Ming Zhang, Jia Wang Ding, Jun Zhang, Wei Qin

中国化学快报. 2010, 21(11): 1378-1381. https://doi.org/10.1016/j.cclet.2010.06.003

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A novel potentiometric detection strategy based on functionalized magnetic nanoparticles has been developed for rapid and sensitive sensing of polyions. Highly dispersed magnetic nanoparticles coated with ion exchanger and plasticizer could promote an in situ cooperative ion-pairing interaction between the ion exchanger and the polyion analyte in sample solution by dramatically reducing the mass-transfer distance. With applying a magnetic field, the nanoparticles can be attached to the surface of ion exchanger free polymeric membrane. The observed potential signals are related to the polyion concentrations. The proposed polymeric membrane electrode exhibits a linear relationship between the greatest potential response slope (dE/dt) and the logarithm of protamine concentration in the range of 0.05-5 μg/mL with a lower detection limit of 0.033 μg/mL.

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Synthesis and characterization of phosphate-modified LiMn₂O₄ cathode materials for Li-ion battery

Qing Lai Jiang, Ke Du, Yan Bing Cao, Zhong Dong Peng, Guo Rong Hu, Ye Xiang Liu

中国化学快报. 2010, 21(11): 1382-1386. https://doi.org/10.1016/j.cclet.2010.04.039

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LiMn₂O₄ spinel cathode materials were modified with 2 wt.% Li-M-PO₄ (M=Co, Ni, Mn) by polyol synthesis method. The phosphate surface-modified LiMn₂O₄ cathode materials were physically characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM) and energy dispersive X-ray spectroscopy (EDS). The charge-discharge test showed that the cycling and rate capacities of LiMn₂O₄ cathode materials were significantly enhanced by stabilizing the electrode surface with phosphate.

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Polyimide-silver nanocomposite containing phosphine oxide moieties in the main chain:Synthesis and properties

Khalil Faghihi, Mohsen Hajibeygi, Meisam Shabanian

中国化学快报. 2010, 21(11): 1387-1390. https://doi.org/10.1016/j.cclet.2010.05.033

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New flame-retardant polyimide-silver nanocomposite containing phosphine oxide moiety in the main chain was synthesized by a convenient ultraviolet irradiation technique. A precursor such as AgNO₃ was used as the source of the silver particles. Polyimide 6 as a source of polymer was synthesized by polycondensation reaction of his (3-aminophenyl) phenyl phosphine oxide 4 with pyromellitic anhydride 5 in the presence of iso-quinoline as base and in m-Cresol solution. The resulting composite film was characterized by FTIR spectroscopy, X-ray diffraction (XRD), transmission electron microscopy (TEM), thermogravimetry (TGA) and differential scanning calorimetry (DSC). The average size of the nanometer Ag particles is about 10 nm. The temperature of 5 and 10% weight loss and also the char yield at 600℃ of polyimide-silver nanocomposite 6a were higher than the pure PI 6.

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2010年, 第21卷, 第11期　刊出日期：2010-11-20

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2010年, 第21卷, 第11期 刊出日期：2010-11-20

2010年, 第21卷, 第11期　刊出日期：2010-11-20