期刊文献+
任意字段
题名或关键词
题名
关键词
文摘
作者
第一作者
机构
刊名
分类号
参考文献
作者简介
基金资助
栏目信息

一种有机小分子手性催化剂的取代物的~1H,^(13)C核磁共振信号归属

Complete ~1H and ^(13)C NMR assignment of a derivative of a new chrial organocatalyst
下载PDF
导出
摘要 3-hydroxy-N-(pyrrolidin-2-ylmethyl)-2-naphthamide(化合物Ⅰ)是最近合成的一种有机小分子催化剂,能催化麦克尔非对称加成反应,且具有高产率、高度立体专一性、反应条件易实现等优点.目前普遍认为:在催化过程中该催化剂萘环上的OH和NH与反应物形成氢键.为了研究该过程,合成了tert-butyl 2-((3-hydroxy-2-naphthamido)methyl)pyrrolidine-1-carboxylate(化合物Ⅱ),应用一系列一维和二维核磁共振(NMR)技术对化合物Ⅱ进行了1H1、3C NMR信号归属.为进一步用NMR实验方法研究催化剂与反应物的氢键作用机理奠定了良好基础,同时为类似化合物的NMR信号归属提供了参考依据. 3- ganocatalyst proceeded in （pyrrolidin-2-ylmethylamino） naphthalen-2 （compound Ⅰ） is a new or which can effectively catalyze asymmetric Michael addition. The reactions good to high yield and excellent enantioselectivities. It＇s generally consid- ered that hydrogen bond is likely formed between the catalyst and the reactant β-nitro- styrene. In the interest of research this process, We synthesized the compound 1-（2- （（3-hydroxynaphthalen-2-ylamino） methyl ） pyrrolidin-l-yl ）-2, 2-dimethylpropan-l-one （compound Ⅱ ）. In this study, 1D and 2D nuclear magnetic resonance （NMR） experiments were used for the assignments of ^1H and ^13C NMR signals of compound Ⅱ , which may be of help for further investigate the catalyzing mechanism. In addition, may sup- ply reference for assignments of similar chemicals.
作者 曹淑芬 赖媛媛 徐国华 刘德立 肖文精 崔艳芳
机构地区 华中师范大学农药与化学生物学教育部重点实验室
出处 《华中师范大学学报（自然科学版）》 CAS CSCD 2008年第4期562-564,591,共4页 Journal of Central China Normal University：Natural Sciences
基金 湖北省自然科学基金项目(2004ABA118).
关键词 ^1H、^13C 核磁共振谱 2D核磁共振谱 手性催化剂 MICHAEL加成 氢键作用 ^1H、^13C NMR 2D NMR hydrogen bonding Michael addition organocatalysis
分类号 O656.22 [理学—分析化学]
  • 相关文献

参考文献10

  • 1Berner O M, Tedeschi L, Enders D. Asymmetric Michael additions to nitroalkenes[J]. European Journal of Organic Chemistry, 2002(12) : 1877-1894.
  • 2List B. Organocatalysis: A complementary catalysis strategy advances organic synthesis[J]. Advanced Synthesis & Catalysis, 2004, 346(9-10) : 1021-1021.
  • 3Seayad J, List B. Asymmetric organocatalysis[J]. Org Biomol Chem, 2005, 3(5) :719-724.
  • 4List B, Pojarliev P, Martin H J. Efficient proline-catalyzed Michael additions of unmodified ketones to nitro olefins[J]. Org Lett, 2001, 3(16) :2423-2425.
  • 5Cao Y J, Lu H H, Lai Y Y, et al. An effective bifunctional thiourea catalyst for highly enantio-and diastereoseleetive Michael addition of eyclohexanone to nitroolefins[J]. Synthesis, 2006(22) :3795-3800.
  • 6Hoang L, Bahmanyar S, Houk K N, et al. Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra-and intermoleeular aldol reactions [J]. J Am Chem Soc, 2003, 125(1) :16-17.
  • 7List B, Hoang L, Martin H J. Asymmetric catalysis special feature part II: New mechanistic studies on the proline-catalyzed aldol reaction[J]. Proc Nat Acad Sci USA, 2004, 101 (16):5839-5842.
  • 8Marquez C, Metzger J O. ESI-MS study on the aldol reaction catalyzed by L-proline [J]. Chem Commun, 2006 (14) : 1539-1541.
  • 9Gryko D, Zimnicka M, Lipiski R. Bransted acids as additives for the direct asymmetric aldol reaction catalyzed by L-proli- nethioamides. Direct evidence for enamine-iminium catalysis [J]. J OrgChem, 2007, 72(3):964-970.
  • 10郑明霞,郝啸,刘福花,李武客,李松军.对硝基偶氮基-1-萘胺与咖啡因希夫碱的合成及其反应机理的探讨[J].华中师范大学学报（自然科学版）,2007,41(2):241-243. 被引量：2

二级参考文献9

  • 1Sabry Suzy M.Application of 2-acetylbutyrolactone to spectrofluorimetry:Fluorescence properties of Schiff bases derived from 2-acetylbutyrolactone and spectrofluorimetric determination of primary amine-containing compounds[J].Journal of Pharmaceutical and Biomedical Analysis,2006,40(5):1057-1067.
  • 2Ali F,Khorrami R.Synthesis and analytical application ofa novel tetradentate N2O2 Schiff base as a chromogenic regent for determination of nickel in some natural food samples[J].Talnta,2005,66(4):813-817.
  • 3Kaan C Emregul.Ece Duzgun,Orhan Atakol.The application of some polydentate Schiff base compounds containing aminic nitrogens as corrosion inhibitors for mild steelin acidic media[J].Corrosion Science.2006.48(10):3 243-3 260.
  • 4Yamini Shrivastava H,Niranjali Devaraj.A Schiff base complex of chromium(Ⅲ):an efficient inhibitor for the pathogenic and invasive potential of Shigella dysenteriae[J].Journal of Inorganic Biochemistry,2004,98(2):387-392.
  • 5Renata Drozdzak,Bart Allaert,Nele Ledoux,et al.Ruthenium complexes bearing bidentate Schiff base ligands as efficient catalysts for organic and polymer syntheses[J].Coordination Chemistry Reviews,2005,249(24);3055-3074.
  • 6Yuichiro Himeda,Nobuko Onozawa-Komatsuzaki,Hideki Sugihara,et al.Transfer hydrogenation of a variety of ketones catalyzed by rhodium complexes in aqueous solution and their application to asymmetric reduction using chiral Schiff base ligands[J].Journal of Molecular Catalysis A,2003,195(2):95-100.
  • 7Chi-Ming Che,Jie-Sheng Huang.Metal complexes of chiral binaphthyl Schiff-base ligands and their application in stereoselective organic transformations[J].Coordination Chemistry Reviews,2003,242(1-2):97-113.
  • 8尹冬冬.有机化学[M].北京:高等教育出版社,2004.
  • 9Badische Aniline,Soda-Fabric Aktiengesell-Schaft.Process for the production of aniline-(4-azo-4)-naphthylamine-1[P].German Covention Application 1411874,1975..

共引文献1

华中师范大学学报（自然科学版）
2008年 第4期

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部