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Volumn 119, Issue 7, 1997, Pages 1599-1608

Synthesis and conformational studies of urobilin difluoroboron complexes. Unprecedented solvent-dependent chiroptical properties of the BF2 chelate of an urobilinoid analogue

Author keywords

[No Author keywords available]

Indexed keywords

BILE PIGMENT; UNCLASSIFIED DRUG; UROBILIN DERIVATIVE;

EID: 0030987091     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961883q     Document Type: Article
Times cited : (45)

References (43)
  • 9
    • 8244230998 scopus 로고    scopus 로고
    • note
    • 6 partially resolved (+)-1a was transformed by reaction with (-)-(S)-1-(1-naphthyl)ethylamine into the corresponding N-[1-(1-naphthyl)ethyl]carboxamide, the absolute configuration of which at C(4) was determined by X-ray diffraction analysis to be R. Within the scope of the present work, enantiomerically pure carboxylic acid (-)-1a has been reacted with (+)-(R)-1-(1-naphthyl)ethylamine, yielding crystalline carboxamide 1c. The X-ray structure analysis of the latter, which has been carried out in the laboratory of Professor Christoph Kratky (Institut für Physikalische Chemie der Universität Graz, Austria) has unequivocally established the absolute configuration at C(4) as S.
  • 12
    • 8244257147 scopus 로고    scopus 로고
    • Dekkers, H. P. J. M. See ref 32, pp 121-152
    • Dekkers, H. P. J. M. See ref 32, pp 121-152.
  • 13
    • 8244264481 scopus 로고    scopus 로고
    • note
    • Private communication from Professor Harry P. J. M. Dekkers (Gorlaeus Laboratories, Department of Chemistry, The University of Leiden, The Netherlands). We are indebted to Professor Dekkers for measurements of the circular polarization of luminiscence of the difluoroboron chelates of urobilins 3 and 4.
  • 14
    • 0348206958 scopus 로고
    • Application of the optical activity to stereochemical determinations
    • Kagan, H. B., Ed.; Vol. 2, Thieme Verlag: Stuttgart, Germany
    • Legrand, M.; Rougier, M. J. Application of the optical activity to stereochemical determinations. In Stereochemistry, Fundamentals and Methods; Kagan, H. B., Ed.; Vol. 2, Thieme Verlag: Stuttgart, Germany, 1977; Vol. 2, pp 47-49.
    • (1977) Stereochemistry, Fundamentals and Methods , vol.2 , pp. 47-49
    • Legrand, M.1    Rougier, M.J.2
  • 16
    • 0000915841 scopus 로고
    • sp = syn-periplanar, sc = syn-clinal, ac = anti-clinal, and ap = anti-periplanar (cf. Klyne, W.; Prelog, V. Experientia 1960, 16, 521).
    • (1960) Experientia , vol.16 , pp. 521
    • Klyne, W.1    Prelog, V.2
  • 24
    • 8244232391 scopus 로고    scopus 로고
    • note
    • 3 are identical.
  • 37
    • 33947321475 scopus 로고
    • Schellman, J. A. J. Chem. Phys. 1966, 44, 55; Acc. Chem. Res. 1968, 1, 144.
    • (1968) Acc. Chem. Res. , vol.1 , pp. 144
  • 42
    • 8244226468 scopus 로고    scopus 로고
    • note
    • Assignments made in a 125.76 MHz COLOC spectrum.
  • 43
    • 8244246907 scopus 로고    scopus 로고
    • note
    • Assignments made in a 125.76 MHz HETCOR spectrum.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.