Contents

Longifolene

(+)-Longifolene

Names
IUPAC name (1R,2S,7S,9S)- 3,3,7-trimethyl- 8-methylenetricyclo- [5.4.0.02,9]undecane
Identifiers
CAS Number	(+): 475-20-7 Y (−): 16846-09-6
3D model (JSmol)	(+): Interactive image (−): Interactive image
Beilstein Reference	5731712 2044263 4663756
ChEBI	(+): CHEBI:49282 N (−): CHEBI:49286
ChemSpider	(+): 16739255 N (−): 1013315
ECHA InfoCard	100.006.812
EC Number	(+): 207-491-2
PubChem CID	(+): 1796220 (−): 1201520
UNII	(+): 3YXH7YY8WM
CompTox Dashboard (EPA)	(+): DTXSID9047045
InChI InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,15-/m1/s1 N Key: PDSNLYSELAIEBU-GUIRCDHDSA-N N
SMILES (+): C[C@]12CCCC([C@@H]3[C@H]1CC[C@@H]3C2=C)(C)C (−): C[C@@]12CCCC([C@H]3[C@@H]1CC[C@H]3C2=C)(C)C
Properties
Chemical formula	C15H24
Molar mass	204.36 g/mol
Density	0.928 g/cm3
Boiling point	254 °C (489 °F; 527 K) (706 mm Hg)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H304, H317, H410
Precautionary statements	P261, P272, P273, P280, P301+P310, P302+P352, P321, P331, P333+P313, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

Longifolene is the common (or trivial) chemical name of a naturally occurring, oily liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated,^[1] Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts.

Longifolene is also one of two most abundant aroma constituents of lapsang souchong tea, because the tea is smoked over pinewood fires.^[2]

Occurrence and syntheses[edit]

Terpentine obtained from Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) contains as much as 20% of longifolene.^[3]

The laboratory synthesis of longifolene has attracted much syntheses.^{[4][5][6][7][8][9][10]}

Longifolene total synthesis by Corey.svg

Biosynthesis[edit]

The biosynthesis of longifolene begins with farnesyl diphosphate (1) (also called farnesyl pyrophosphate) by means of a cationic polycyclization cascade. Loss of the pyrophosphate group and cyclization by the distal alkene gives intermediate 3, which by means of a 1,3-hydride shift gives intermediate 4. After two additional cyclizations, intermediate 6 produces longifolene by a 1,2-alkyl migration.

Reactions[edit]

It reacts with borane to give the derivative dilongifolylborane, which is a chiral hydroborating agent.^[11]

References[edit]

External links[edit]

• Longifolene Total Syntheses @ SynArchive.com