Pinane

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Pinane
PinaneIsomers.svg
Identifiers
3D model (JSmol)
1847301
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.790 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-467-1
  • trans:229-978-9
PubChem CID
UNII
UN number 3295
  • InChI=1S/C10H18/c1-7-4-5-8-6-9(7)10(8,2)3/h7-9H,4-6H2,1-3H3
    Key: XOKSLPVRUOBDEW-UHFFFAOYSA-N
  • trans:InChI=1S/C10H18/c1-7-4-5-8-6-9(7)10(8,2)3/h7-9H,4-6H2,1-3H3/t7-,8-,9-/m0/s1
    Key: XOKSLPVRUOBDEW-CIUDSAMLSA-N
  • cis:InChI=1S/C10H18/c1-7-4-5-8-6-9(7)10(8,2)3/h7-9H,4-6H2,1-3H3/t7-,8+,9+/m1/s1
    Key: XOKSLPVRUOBDEW-VGMNWLOBSA-N
  • CC1CCC2CC1C2(C)C
  • trans:C[C@H]1CC[C@H]2C[C@@H]1C2(C)C
  • cis:C[C@@H]1CC[C@H]2C[C@@H]1C2(C)C
Properties
C10H18
Molar mass 138.254 g·mol−1
Appearancecolorless liquids
Boiling point 167.2 – 168 °C (cis)
164 °C (trans)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pinane describes a pair of isomeric hydrocarbons. The isomers, actually diastereomers, are both chiral. They are the cis and trans isomers arising from the hydrogenation of the terpenes pinene. Both isomers undergo reaction with air (autoxidation) to give 2-pinane hydroperoxides. [1] Partial reduction of these isomers gives 2-pinanol. [2] Pyrolysis of pinane gives dimethyloctadienes. [3]

Formation of dimethyloctadienes Dimethyloctadienes.svg
Formation of dimethyloctadienes


References

  1. ↑ Erman, Mark B.; Kane, Bernard J. (2008). "Chemistry Around Pinene and Pinane: A Facile Synthesis of Cyclobutanes and Oxatricyclo-Derivative of Pinane from cis- and trans-Pinanols". Chemistry & Biodiversity. 5 (6): 910–919. doi:10.1002/cbdv.200890104. PMID   18618388. S2CID   24782774.
  2. ↑ Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN   3527306730.
  3. ↑ Sagorin, Gilles; Cazeils, Emmanuel; Basset, Jean-François; Reiter, Maud (2021). "From Pine to Perfume". CHIMIA. 75 (9): 780–787. doi:10.2533/chimia.2021.780. PMID   34526184.
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