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196436

Sigma-Aldrich

(1R)-(−)-Fenchone

≥98%

Synonym(s):

(−)-1,3,3-Trimethyl-2-norbornanone, (−)-Fenchone, (1R)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one

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About This Item

Empirical Formula (Hill Notation):
C10H16O
CAS Number:
7787-20-4
Molecular Weight:
152.23
Beilstein:
2042710
EC Number:
232-107-5
MDL number:
MFCD00151104
UNSPSC Code:
12352200
PubChem Substance ID:
24851759
NACRES:
NA.22

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
GHS09

Hazard Statements

H411

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Chronic 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

151.7 °F - closed cup

Flash Point(C)

66.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
(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)
Santiago de la Moya Cerero et al.
The Journal of organic chemistry, 68(4), 1451-1458 (2003-02-15)
Valuable chiral sources of C(10)-substituted camphors and C(10)-substituted fenchones can be straightforwardly obtained by treatment of an appropriate, easily obtainable, camphor- or fenchone-derived 2-methylenenorbornan-1-ol with an electrophilic reagent. The process takes place via a tandem regioselective carbon-carbon double-bond addition/stereocontrolled Wagner-Meerwein
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