陈应春
博士 教授
四川大学 华西药学院药物化学系
从事新型(手性)有机和金属催化剂的合成及(不对称)催化研究、新型可回收催化剂的合成及反应、新型水溶性药物及手性药物合成等方面的研究工作
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- 姓名:陈应春
- 目前身份:在职研究人员
- 担任导师情况:
- 学位:博士
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学术头衔:
博士生导师
- 职称:高级-教授
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学科领域:
有机化学
- 研究兴趣:从事新型(手性)有机和金属催化剂的合成及(不对称)催化研究、新型可回收催化剂的合成及反应、新型水溶性药物及手性药物合成等方面的研究工作
陈应春,博士,1972年生于重庆,现为四川大学华西药学院教授、博士生导师。先后于天津南开大学化学系、华西医科大学药学院、中科院成都有机化学研究所完成本科、硕士和博士学习,毕业后先后在中科院成都有机化学研究所、香港大学化学系进行博士后研究。2003年10月到四川大学工作。
主要从事新型手性有机催化剂的设计、合成及不对称催化反应研究以及生理活性物质的设计、合成等方面的工作。重点在手性有机小分子催化的不对称合成领域开展研究并获得了系列成果:1)在基于氢键活化的手性硫脲等催化剂的设计及其促进的不对称反应进行了多方面研究,建立了结构、功能多样的基于氢键活化的有机催化剂库,在多种不对称催化反应中实现了好的立体控制,发展了多种重要手性中间体、特别是非天然氨基酸的不对称合成方法。2)在手性伯、仲胺通过烯胺、二烯胺、三烯胺及亚胺盐机制催化饱和或不饱和醛和酮以及叔胺、叔膦等作为Lewis base催化Morita-Baylis-Hillman产物碳酸酯的不对称转化反应等领域开展了系统的研究,在催化剂、催化机制及新型催化反应的设计等多方面进行了积极探索。课题组首先采用从天然金鸡纳碱衍生的手性伯胺在催化不饱和酮的不对称反应方面取得好结果,为开拓不饱和酮的新型不对称反应以及发展新的手性胺催化体系进行了创造性探索;首次发展了手性胺催化2,4-二烯醛和2,4-二烯酮的三烯胺催化机制,建立了不饱和羰基化合物的多类远端不对称反应新途径;建立了数十种多官能团、多手性中心化合物的合成新方法,建立数千个新型化合物库;通过计算机辅助和细胞筛选实验,发现多类新颖的抗肿瘤、抗肺纤维化等新结构物质,为进一步发现和设计新型生理活性手性化合物奠定坚实基础。
作为通讯作者已在Chem. Soc. Rev.、Acc. Chem. Res.、Nat. Chem.、J. Am. Chem. Soc.、Angew. Chem. Int. Ed.等国内外学术期刊上发表SCI论文130余篇,总他引超过5500次。参与《Cinchona Alkaloids in Synthesis & Catalysis: Ligands, Immobilization and Organocatalysis》、《Asymmetric Organocatalysis》、《Organocatalytic Ring-Forming Reactions》等英文专著章节的撰写工作。完成了包括国家Ⅰ类抗癌新药Cambretastatin A-4 水溶性前药、国家Ⅰ类抗脓毒症新药KB甲烷磺酸盐等药物的合成研究(均进入临床研究)。
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成果数
19
陈应春, Jian-Wu Xie, b, c, Lei Yue, a, Dong Xue, Xiao-Li Ma, Ying-Chun Chen, *a, Yong Wu, Jin Zhu b and Jin-Gen Deng*b
Chem. Commun., 2006, 1563-1565,-0001,():
-1年11月30日
The first highly regio-, chemo-, diastereo- and enantioselective direct vinylogous Michael addition of a,a-dicyanoolefins to a,b-unsaturated aldehydes is described, employing readily available chiral a,a-diarylprolinol salts as iminium organocatalysts.
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陈应春, Yan-Kai Liu, †, Rui Li, ‡, Lei Yue, Bang-Jing Li, Ying-Chun Chen, *, Yong Wu, † and Li-Sheng Ding‡
Org. Lett., Vol. 8, No.8, 2006. 1521-1524,-0001,():
-1年11月30日
The chemoselective ring opening of N-tosyl aziridines with aldehydes catalyzed by an N-heterocyclic carbene was investigated under aerobic conditions. Unexpected carboxylates of 1,2-amino alcohols from the corresponding aldehydes, rather than the acyl anion ring-opened β-amino ketones, were exclusively obtained. A plausible mechanism for this unprecedented carbene-mediated reaction was also proposed.
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陈应春, Dong Xue, †, ‡, Ying-Chun Chen, §, Xin Cui, Qi-Wei Wang, Jin Zhu, † and Jin-Gen Deng*
J. Org. Chem. 2005, 70, 3584-3591,-0001,():
-1年11月30日
al hydride had been applied to the reduction of various activated olefins. The electron-withdrawing ability of functional groups substituted on CdC bonds at the R- or β-position had strong influence on the reactivity. In addition, a wide variety of chiral diamine-Ru(Ⅱ)-(arene) systems was investigated to explore the asymmetric transfer hydrogenation of prochiral R, R-dicyanoolefins. Two parameters had been systematically studied, (i) the structure of the N-sulfonylated chiral diamine ligands, in which several chiral diamines substituted on the benzene ring of DPEN were first reported, and (ii) the structure of the metal precursors, and high enantioselectivitiy (up to 89% ee) at the â-carbon was obtained.
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陈应春, Wei Chen, [a], Rui Li, [b], Bo Han, Bang-Jing Li, Ying-Chun Chen, *[a], Yong Wu, Li-Sheng Ding, [b] and Dan Yang[c]
Eur. J. Org. Chem. 2006, 1177-1184,-0001,():
-1年11月30日
New, bulky N,N-disubstituted acyclic and cyclic bis (thiourea) ligands have been designed and synthesized. Their palladium(0) complexes are very stable and are active catalysts for Heck and Suzuki coupling reactions of aryl iodides and bromides under aerobic conditions. Good TONs and TOFs were achieved in the coupling reactions [for PhI, TONs up to 1000000 and TOFs up to 200000 (h–1); for activated aryl bromide, TONs up to 89000]. In addition, further studies were conducted to know more about the nature of these catalysts. The active catalyst was found to be the chelate complex containing the bis(thiourea) and Pd in a 1:1 ratio. However, unlike a monothiourea, further coordination can occur to give a coordinatively saturated complex when bis(thiourea) and Pd are combined in a 2:1 ratio; this complex is catalytically inactive in coupling reactions.
Cross-coupling, Homogeneous catalysis, Palladium, Sligands
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【期刊论文】Synthesis of Dendritic Catalysts and Application in Asymmetric Transfer Hydrogenation
陈应春, Ying-Chun Chen, *, †, Tong-Fei Wu, ‡, Lin Jiang, Jin-Gen Deng, Hui Liu, Jin Zhu, ‡ and Yao-Zhong Jiang‡
J. Org. Chem. 2005, 70, 1006-1010 ,-0001,():
-1年11月30日
Fr
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陈应春, Dan Yang, *, Ying-Chun Chen, and Nian-Yong Zhu
Org. Lett., Vol. 6, No.10, 2004, 1577-1580 ,-0001,():
-1年11月30日
We demonstrate that sterically bulky N,N'-disubstituted cyclic thiourea-Pd(0) complexes are air- and moisture-stable and highly active catalysts for palladium-catalyzed Heck reaction of aryl iodides and bromides with olefins (TONs up to 500 000 for the reaction of PhI and methyl acrylate). Even activated aryl chlorides can undergo complete conversion in Bu4NBr in the presence of 1 mol% Pd catalyst.
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陈应春, Wei Chen, a, Rui Li, b, Yong Wu, Li-Sheng Ding, Ying-Chun Chen*a
Synthesis 2006, No.18, 3058-3062,-0001,():
-1年11月30日
The synthesis of novel self-supported thiourea-PdCl2 complexes is described. The heterogeneous catalysts exhibited high catalytic activities in the Suzuki coupling reaction of aryl bromides and aryl boronic acids in neat water under aerobic conditions. Moreover, the catalysts could be easily reused without diminishing the catalytic activity.
thiourea, palladium, self-supported, heterogeneous, Suzuki reaction
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陈应春, Qing-Ping Liu, b, c, Ying-Chun Chen, *a, Yong Wu, a, Jin Zhu, Jin-Gen Deng*a
Synlett 2006, No.10, 1503-1506,-0001,():
-1年11月30日
A novel strategy to synthesize heterogeneous starshaped oxime-palladacycle catalysts, which exhibited good catalytic activity and recyclability in the Suzuki coupling of aryl bromides and chlorides, was described.
self-supported, palladacycle, heterogeneous, Suzuki coupling
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【期刊论文】Synthesis and Cytotoxic Activity of Novel Water-soluble Prodrugs of Combretastatin A-4
陈应春, Zhi Quan YONG, Xiao Ping XU, Ying Chun CHEN*, Xu BAO, Ling Ling WENG*, Hu ZHENG
Chinese Chemical Letters Vol. 17, No.1, pp 23-26, 2006,-0001,():
-1年11月30日
Novel water-soluble prodrugs of combretastatin A-4 (5-8) were synthesized and evaluated for their in vitro cytotoxicity against lung carcinoma A549. Compound 5, bearing phosphoryl choline (PC) moiety, showed 90% inhibition at 32μg/mL concentration after 24h. The findings showed the PC derivative would be a promising candidate for the development of new water-soluble prodrug of cytotoxic combretastatin A-4.
Combretastatin A-4,, cytotoxicity,, phosphoryl choline,, water-soluble,, prodrug.,
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【期刊论文】Multiple Dendritic Catalysts for Asymmetric Transfer Hydrogenation
陈应春, Ying-Chun Chen, †, Tong-Fei Wu, Jin-Gen Deng, *, Hui Liu, Xin Cui, Jin Zhu, Yao-Zhong Jiang, Michael C.K. Choi, ‡ and Albert S.C. Chan‡
J. Org. Chem. 2002, 67, 5301-5306 5301,-0001,():
-1年11月30日
The first and second generation multiple dendritic ligands based on chiral diamine were synthesized in a convergent approach and were well-characterized by NMR and MS techniques. Their ruthenium complexes prepared in situ had good solubility in the reaction medium (azeotrope of formic acid and triethylamine) and demonstrated high catalytic activity and enantioselectivity comparable to monomeric catalysts in the asymmetric transfer hydrogenation of ketones and imines. Quantitative yields and for some cases a slightly higher enantioselectivity (up to 98.7% ee) were obtained in the dendritic catalysis. Considering the high local catalyst concentrations at the periphery, diones were tested for the possible synergic reactivity between catalytic units at the surface, while no apparent differences were noted.
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