Isoborneol
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Names | |
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IUPAC name (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol | |
Identifiers | |
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3D model (JSmol) | |
ChEBI |
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ChEMBL | |
ChemSpider | |
PubChem CID | |
UNII |
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UN number | 1312 |
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Properties | |
C10H18O | |
Molar mass | 154.253 g·mol−1 |
Appearance | white or colorless solid |
Melting point | 212–214 °C (414–417 °F; 485–487 K) + or -; 210–215 °C for rac |
Hazards | |
GHS labelling:[1] | |
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Warning | |
H228 | |
P210, P240, P241, P280, P370+P378 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Isoborneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an exo position. The endo diastereomer is called borneol. Being chiral, isoborneol exists as enantiomers.
Preparation
[edit]Isoborneol is synthesized commercially by hydrolysis of isobornyl acetate. The latter is obtained from treatment of camphene with acetic acid in the presence of a strong acid catalyst.[2]
It can also be produced by reduction of camphor:
Isoborneol derivatives as chiral ligands
[edit]Derivatives of isoborneol are used as ligands in asymmetric synthesis.[3]
- (2S)-(−)-3-exo-(morpholino)isoborneol or MIB[4] with a morpholine substituent in the α-hydroxyl position.
- (2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB[5] with a dimethylamino substituent in the α-hydroxyl position
References
[edit]- ^ "(+)-Isoborneol". pubchem.ncbi.nlm.nih.gov. Retrieved 1 December 2022.
- ^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
- ^ Yus, Miguel; Ramón, Diego (2007). "Chiral Ligands with an Isoborneol-10-sulfonamide Structure: A Ten-Year Odyssey". Synlett. 2007 (15): 2309–2320. doi:10.1055/s-2007-985602.
- ^ Chen, Y. K.; Jeon, S.-J.; Walsh, P. J.; Nugent, W. A. (2005). "(2S)-(−)-3-exo-(Morpholino)isoborneol". Organic Syntheses. 82: 87. doi:10.15227/orgsyn.082.0087.
- ^ White, J. D.; Wardrop, D. J.; Sundermann, K. F. (2002). "(2S)-(−)-3-exo-(Dimethylamino)isoborneol". Organic Syntheses. 79: 130. doi:10.15227/orgsyn.079.0130.