A Many-Faced Alkaloid: Polymorphism of (–)-Monophyllidin
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of (–)- and (+)-Monophyllidin
2.2. Synthesis of the Ester of (–)-Monophyllidin and (+)-Menthol
3. Crystallographic Characterization of (–)-Monophyllidin Polymorphs (P-I to P-VI)
3.1. (–)-Monophyllidin Polymorph-I (P-I) (Crystallized from CH3CN; Space Group P212121; Crystal System Orthorhombic)
3.2. (–)-Monophyllidin Polymorph-II (P-II) (Crystallized from CH3CN; Space Group C2; Crystal System Monoclinic)
3.3. (–)-Monophyllidin Polymorph-III (P-III) (Crystallized from CHCl3; Space Group P1; Crystal System Triclinic)
3.4. (–)-Monophyllidin Polymorph-IV (P-IV) (Obtained from Recrystallization in Ethanol Followed by Acetonitrile; Space Group P1; Crystal System Triclinic)
3.5. (–)-Monophyllidin Polymorph-V (P-V) (Obtained from Water; Space Group P21; Crystal System Monoclinic)
3.6. (–)-Monophyllidin Polymorph-VI (P-VI) (Plate Isolated from the Primary Crystal Mixture; Space Group P212121; Crystal System Orthorhombic)
3.7. (S)-(1S,2R,5S)-2-Isopropyl-5-methylcyclohexyl1-(3-acetyl-2-hydroxy-4,6-dimethoxy-benzyl) pyrrolidine-2-carboxylate Hydrochloride (5xHCl).
3.8. Summary and Conclusions
4. Materials and Methods
Chemistry
General Information
Synthetic procedures (for NMR interpretation and spectra see Supplementary Materials)
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–5 are available from HG. |
Solvent | ID | Space Group | mp [°C] | Crystal Habitus |
---|---|---|---|---|
acetonitrile | P-I | P212121 | 161–162 | block-like |
acetonitrile | P-II | C2 | 158–160 | needles |
acetonitrile | P-VI | P212121 | nd (singleton) | plates |
chloroform | P-III | P1 | 158–159 | needles |
ethanol-acetonitrile | P-IV | P1 | 158–159 | needles |
water | P-V | P21 | 155–156 | blocks |
ID | Space Group | mp [°C] | Crystal Habitus | Guest Molecules | (–)-3a: Guest(s) |
---|---|---|---|---|---|
P-I | P212121 | 161–162 | blocks | CH3CN | 1:1 |
P-II | C2 | 158–160 | needles | CH3CN:water | 2:1:2 |
P-III | P1 | 158–159 | needles | CHCl3:water | 2:2:1 |
P-IV | P1 | 158–159 | needles | H2O | 2:5 |
P-V | P21 | 155–156 | blocks | H2O | 2:1 |
P-VI | P212121 | nd | plates | H2O | 2:1 |
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Dank, C.; Wurzer, R.; Felsinger, S.; Bugl, R.; Kählig, H.; Hela, W.; Roller, A.; Gstach, H. A Many-Faced Alkaloid: Polymorphism of (–)-Monophyllidin. Molecules 2020, 25, 449. https://doi.org/10.3390/molecules25030449
Dank C, Wurzer R, Felsinger S, Bugl R, Kählig H, Hela W, Roller A, Gstach H. A Many-Faced Alkaloid: Polymorphism of (–)-Monophyllidin. Molecules. 2020; 25(3):449. https://doi.org/10.3390/molecules25030449
Chicago/Turabian StyleDank, Christian, Richard Wurzer, Susanne Felsinger, Ricarda Bugl, Hanspeter Kählig, Wolfgang Hela, Alexander Roller, and Hubert Gstach. 2020. "A Many-Faced Alkaloid: Polymorphism of (–)-Monophyllidin" Molecules 25, no. 3: 449. https://doi.org/10.3390/molecules25030449