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Sigma-Aldrich

(1R)-(−)-Fenchone

≥98%

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Synonym(s):
(−)-1,3,3-Trimethyl-2-norbornanone, (−)-Fenchone, (1R)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one
Empirical Formula (Hill Notation):
C10H16O
CAS Number:
Molecular Weight:
152.23
Beilstein/REAXYS Number:
2042710
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥98%

form

liquid

optical activity

[α]24/D −50.5°, neat

refractive index

n20/D 1.461 (lit.)

bp

192-194 °C (lit.)

mp

5-6 °C (lit.)

density

0.948 g/mL at 25 °C (lit.)

SMILES string

CC1(C)C2CCC(C)(C2)C1=O

InChI

1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m0/s1

InChI key

LHXDLQBQYFFVNW-OIBJUYFYSA-N

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General description

(1R)-(-)-Fenchone is a bridged bicyclic ketone found in fennel oil and thuja oil.

Application

(1R)-(-)-Fenchone undergoes condensation with pyridinylalkylamines to form chiral iminopyridine ligands, which find applications in enantioselective copper-catalyzed Henry (nitro aldol) reaction. It may also be used in the preparation of enantiopure C(7)-anti-substituted fenchones as new chiral sources.

pictograms

Environment

hcodes

Hazard Classifications

Aquatic Chronic 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

151.7 °F - closed cup

flash_point_c

66.5 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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First access to enantiopure C (7)-substituted fenchones: new norbornane-based chiral materials from the chiral pool.
Marti'nez AG, et al.
Tetrahedron Asymmetry, 14(12), 1607-1609 (2003)
Regio-and stereochemical course of the ring expansion of bridged bicyclic ketones to spirocyclic a-keto tetrahydrofurans.
Paquette LA, et al.
The Journal of Organic Chemistry, 57(14), 3956-3965 (1992)
(1R)-(-)-Fenchone.
Bond AD and Davies JE.
Acta Crystallographica Section E, Structure Reports Online, 57(11), o1034-o1035 (2001)
Modular iminopyridine ligands. Application to the enantioselective copper (II)-catalyzed Henry reaction.
Blay G, et al.
Tetrahedron Asymmetry, 17(14), 2046-2049 (2006)
B Simándi et al.
Journal of agricultural and food chemistry, 47(4), 1635-1640 (1999-11-24)
Ground fennel seeds were extracted with supercritical carbon dioxide. Small-scale subsequent extractions of the same sample showed that the composition of volatile compounds was changed with the extension of extraction time and only principal volatile components (limonene, fenchone, methylchavicol, and

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