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Isoborneol

From Wikipedia, the free encyclopedia
Isoborneol
Names
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
UN number 1312
  • +: InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1
    Key: DTGKSKDOIYIVQL-OYNCUSHFSA-N
  • -: InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1
    Key: DTGKSKDOIYIVQL-MRTMQBJTSA-N
  • +: C[C@]12CC[C@H](C1(C)C)C[C@@H]2O
  • -: C[C@@]12CC[C@@H](C1(C)C)C[C@H]2O
  • rac: CC1(C2CCC1(C(C2)O)C)C
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]
GHS02: Flammable
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

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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

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Derivatives of isoborneol are used as ligands in asymmetric synthesis.[3]

References

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  1. ^ "(+)-Isoborneol". pubchem.ncbi.nlm.nih.gov. Retrieved 1 December 2022.
  2. ^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.