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(2R,3R,5R)-2-

Ellis1, Spek

  • 1Bijvoet Center for Biomolecular Research, Department of Crystal and Structural Chemistry, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands. d.d.ellis@chem.uu.nl.

Acta Crystallographica. Section C, Crystal Structure Communications
|September 15, 2000
PubMed
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This study reports the molecular structures of two chiral cyclohexanones derived from R-(-)-carvone. Crystal analyses confirmed their conformations, as spectroscopic methods like NMR and IR were insufficient to determine stereochemistry.

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Spectroscopy

Background:

  • Chiral cyclohexanones are important structural motifs in organic chemistry.
  • R-(-)-carvone serves as a versatile chiral precursor for synthesizing complex molecules.
  • Understanding the conformational properties of these compounds is crucial for their applications.

Purpose of the Study:

  • To elucidate the molecular structures and conformational properties of two novel chiral cyclohexanones derived from R-(-)-carvone.
  • To investigate the limitations of spectroscopic techniques (NMR, IR) in determining the stereochemistry of these complex molecules.
  • To utilize X-ray crystallography for unambiguous structural and conformational analysis.

Main Methods:

  • Synthesis of two chiral cyclohexanone derivatives from R-(-)-carvone.

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  • Characterization using Nuclear Magnetic Resonance (NMR) and Infrared (IR) spectroscopy.
  • Single-crystal X-ray diffraction analysis to determine molecular structures and conformations.

    • Main Results:

    • The molecular structure of compound (I) (C(17)H(26)O(3)) revealed a chair conformation for the six-membered ring and a cis configuration for the fused furofuranyl substituent.
    • Compound (II) (C(17)H(23)NO) exhibited a decalin core with one ring in a chair conformation and the other in a half-boat conformation.
    • Spectroscopic data (NMR, IR) were unable to definitively establish the stereochemistry at all chiral centers.

    Conclusions:

    • X-ray crystallography provided definitive structural and conformational insights for both chiral cyclohexanones.
    • The study highlights the complementary roles of spectroscopy and crystallography in characterizing complex organic molecules.
    • Conformational analysis of these R-(-)-carvone derivatives offers valuable data for synthetic and medicinal chemistry endeavors.