| 用于芳香胺和醇NMR对映体检测的松香基膦试剂的合成 |
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| 引用本文： | 吴强,姚贵阳,朱永涛,王恒山,何春欢,潘英明. 用于芳香胺和醇NMR对映体检测的松香基膦试剂的合成[J]. 有机化学, 2012, 32(5): 900-906 |
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| 作者姓名： | 吴强 姚贵阳 朱永涛 王恒山 何春欢 潘英明 |
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| 作者单位： | 广西师范大学化学化工学院药用资源化学与药物分子工程重点实验室 桂林541004 |
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| 基金项目： | 973计划前期研究专项(No.2011CB512005);国家自然科学基金(No.20762001);广西自然科学基金重点(No.2011GXNSFD018010);广西新世纪十百千人才工程人选(No.2007228)资助项目~~ |
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| 摘 要： | 以松香为原料通过三步反应高产率合成手性二醇3和手性单醇6,将它们用作手性助剂现场制备有机膦衍生试剂,分别对单官能团手性底物(单胺、单醇)和双官能团底物(双胺、双醇及氨基醇)进行衍生,通过31P NMR测定,其芳基底物非对映体衍生物的膦化学位移差异值(Δδp)在3.08～0.10之间,均能够在测定条件下实现对映体峰的基线分离.用于α-萘乙胺和1,1’-联二萘酚(BINOL)样品对映体过量值测定,相对误差小于±2%.
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| 关 键 词： | 31PNMR 对映体过量检测 松香基膦试剂 |
Synthesis of Rosin Derived Chiral Derivatizing Agents for 31P NMR Assays of Amine or Alcohol and Amino Alcohol Enantiomers |
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| Wu, Qiang , Yao, Guiyang , Zhu, Yongtao , Wang, Hengshan , He, Chunhuan , Pan, Yingming. Synthesis of Rosin Derived Chiral Derivatizing Agents for 31P NMR Assays of Amine or Alcohol and Amino Alcohol Enantiomers[J]. Chinese Journal of Organic Chemistry, 2012, 32(5): 900-906 |
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| Authors: | Wu Qiang Yao Guiyang Zhu Yongtao Wang Hengshan He Chunhuan Pan Yingming |
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| Affiliation: | Wu,Qiang Yao,Guiyang Zhu,Yongtao Wang,Hengshan* He,Chunhuan Pan,Yingming*(Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources,School of Chemistry & Chemical Engineering,Guangxi Normal University,Guilin 541004) |
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| Abstract: | Chiral alcohols 3 and 6 were synthesized in optically pure forms from easily available rosin acid in short-steps.A comprehensive protocol for the enantiomeric excess assays of mono-or di-functional-grouped chiral secondary amine or alcohol has been established by using them as chiral auxiliary for chiral phosphorus derivatizing reagents(CPDA) in 31P NMR tests.Chemical shift difference(Δδp) values ranging from 3.08 to 0.10 between two diastereoisomers of the CPDAs and the aryl substrates were obtained.The enantiomeric excess of 1-(1-naphthyl)ethylamine and 1,1’-bi(2-naphthol) is determined using our CPDA,and the results showed that the relative error was less than ±2%. |
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| Keywords: | 31P NMR enantiomeric excess detection rosin derived phosphine agents |
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