A COCON analysis of proton-poor heterocycles - Application of carbon chemical shift predictions for the evaluation of structural proposals

European Journal of Organic Chemistry

Volumn , Issue 3, 1999, Pages 579-586

  Köck, Matthias ^a   Junker, Jochen ^a   Maier, Walter ^b   Will, Martin ^b   Lindel, Thomas ^c  

^a GOETHE UNIVERSITY   (Germany)

^b BASF SE   (Germany)

^c UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Computational method; Constitutional analysis; HMBC; Natural products; Structure elucidation

Indexed keywords

11 HYDROXYROTENONE; AFLATOXIN B1; HAEMOVENTOSIN; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; COMPUTER PROGRAM; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 0042758120     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199903)1999:3<579::aid-ejoc579>3.0.co;2-%23     Document Type: Article

References (42)

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34. 13C-NMR data of rotenone was already published: L. Crombie, G. W. Kilbee, D. A. Whiting, J. Chem. Soc., Perkin Trans. 1 1975, 1497-1499; G. Blaskó, H.-L. Shieh, J. M. Pezzuto, G. A. Cordell, J. Nat. Prod. 1989, 52, 1363-1366.
35. 13C NMR, 1D DEPT (90 and 135), COSY, TOCSY, ROESY, HSQC and HMBC.
36. The calculation time was 2 h 9 min 57 s. By using the 1,1-ADEQUATE data additionally the number of possible structures is reduced to 78 (calculation time of 0.8 s).
37. 1H) = 12.4 ppm which indicates a hydrogen bond.
38. The calculation time was 1 h 8 min 7 s. By using the 1,1-ADEQUATE data additionally the number of possible structures is reduced to 38 (calculation time of 0.5 s).
39. 13C chemical shift calculations.
40. CH couplings.
41. The defined fixed bonds for the data set of 3 have a dramatic influence on the number of structures and the calculation time. COCON generated 29175 possible constitutions using COSY, HMBC data and fixed bonds (calculation time of 2 h 8 min 34 s). The number of structures is reduced to 219 if 1,1-ADEQUATE data is used (calculation time 45.5 s).
42. [36] by a dithionite reduction.