13C NMR of coumarins. V†—3-prenylated coumarins

作者: F. A. Macias , R. Hernández-Galán , G. M. Massanet , F. Rodriguezluis , M. Vasquez

DOI: 10.1002/MRC.1260280814

关键词: Carbon-13 NMRChemical solutionOrganic chemistryTerpenoidStereochemistryNuclear magnetic resonance spectroscopyBicyclic moleculePrenylationLactoneChemistry

摘要: 13C NMR data of nineteen coumarins, twelve which bear a prenyl (isoprenoid) side-chain at C-3, are reported and compared with those the C-3 unsubstituted compounds. Unlike linear isomers, no γ-effect is observed in corresponding angular derivatives; this proposed as spectroscopic criterion for distinguishing between these isomers.

参考文章(23)
R.D.H. Murray, M. Sutcliffe, P.H. McCabe, Claisen rearrangements-IV Tetrahedron. ,vol. 27, pp. 4901- 4906 ,(1971) , 10.1016/S0040-4020(01)98195-5
R.D.H. Murray, M.M. Ballantyne, K.P. Mathai, Claisen rearrangements—III Tetrahedron. ,vol. 27, pp. 1247- 1251 ,(1971) , 10.1016/S0040-4020(01)90873-7
F. A. Macias, G. M. Massanet, F. Rodríguez-Luis, J. Salvá, 13C NMR of coumarins. III—Simple coumarins Magnetic Resonance in Chemistry. ,vol. 27, pp. 892- 894 ,(1989) , 10.1002/MRC.1260270913
Maria Grazia Valle, Giovanni Appendino, Gian Mario Nano, Vincenzo Picci, Prenylated coumarins and sesquiterpenoids from Ferula communis Phytochemistry. ,vol. 26, pp. 253- 256 ,(1986) , 10.1016/S0031-9422(00)81522-8
Giovanni Appendino, Silvia Tagliapietra, Pierluigi Gariboldi, Gian Mario Nano, Vincenzo Picci, ω-Oxygenated prenylated coumarins from Ferula communis Phytochemistry. ,vol. 27, pp. 3619- 3624 ,(1988) , 10.1016/0031-9422(88)80778-7
A. Gonzalez, V. Darias, G. Alonso, J. Boada, F. Rodriguez–Luis, Cytostatic activity of some Canary Islands species of Rutaceae. Planta Medica. ,vol. 31, pp. 351- 356 ,(1977) , 10.1055/S-0028-1097543
F. A. Macias, G. M. Massanet, F. Rodriguez-Luis, J. Salvá, 13C NMR of coumarins. IV, Furanocoumarins Magnetic Resonance in Chemistry. ,vol. 28, pp. 219- 222 ,(1990) , 10.1002/MRC.1260280305
J Salvá, FR Luis, E Pando, GM Massanet, RH Galan, Synthesis of C-8 prenylated and angular 3-(1',1'-dimethylallyl)coumarins Heterocycles. ,vol. 31, pp. 255- 258 ,(1990) , 10.3987/COM-89-5121
Bonaventure Tchaleu Ngadjui, Johnson Foyere Ayafor, Beibam L. Sondengam, Joseph D. Connolly, Coumarins from Clausena anisata Phytochemistry. ,vol. 28, pp. 585- 589 ,(1989) , 10.1016/0031-9422(89)80056-1
Francisco Rodríguez-Luis, Guillermo M. Massanet, Enrique Pando, Javier Salv�, Synthesis of 3-(1',1'-Dimethylallyl)coumarins: Gravelliferone, Chalepin and Rutamarin Heterocycles. ,vol. 26, pp. 1541- 1548 ,(1987) , 10.3987/R-1987-06-1541