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Updated: May 22, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(1S,2E,6R,7aR)-2-Benzyl-idene-1,6-dihy-droxy-2,3,5,6,7,7a-hexa-hydro-1H-pyrrolizin-3-one
This study confirms the E conformation of a double bond in a novel compound using NMR data. Molecular structure analysis reveals specific ring conformations and hydrogen bonding in the crystal lattice.
Area of Science:
- Organic Chemistry
- Crystallography
- Spectroscopy
Background:
- Pyrrolizine derivatives are important scaffolds in medicinal chemistry.
- Understanding the precise three-dimensional structure of organic molecules is crucial for predicting their properties and biological activity.
Purpose of the Study:
- To elucidate the complete three-dimensional structure of the title compound, C(14)H(15)NO(3).
- To confirm the double bond configuration and analyze the conformational preferences of the pyrrolizine unit.
- To investigate intermolecular interactions within the crystal structure.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Two-dimensional Nuclear Magnetic Resonance (NMR) spectroscopy was utilized to confirm the double bond geometry.
- Hooft and Flack parameters were calculated to establish the absolute configuration.
Main Results:
- The double bond in the title compound was confirmed to have E configuration.
- The five-membered rings within the pyrrolizine unit adopt C-envelope conformations.
- Intermolecular O-H⋯O hydrogen bonds were observed, linking molecules in the crystal structure.
- The absolute configuration of the molecule was successfully determined.
Conclusions:
- The study provides a comprehensive structural characterization of the title compound.
- The conformational analysis offers insights into the stereochemistry of pyrrolizine derivatives.
- The established absolute configuration is vital for potential pharmaceutical applications.
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