196436
(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:
Molecular Weight:
152.23
UNSPSC Code:
12352200
NACRES:
NA.22
PubChem Substance ID:
EC Number:
232-107-5
Beilstein/REAXYS Number:
2042710
MDL number:
Assay:
≥98%
Form:
liquid
Quality Segment
assay
≥98%
form
liquid
optical activity
[α]24/D −50.5°, neat
reaction suitability
reagent type: chrial catalyst
refractive index
n
bp
192-194 °C (lit.)
mp
5-6 °C (lit.)
density
0.948 g/mL at 25 °C (lit.)
functional group
ketone
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
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.
Hazard Codes
Precautionary Statements
Hazard Classifications
Aquatic Chronic 2
Storage Class
10 - Combustible liquids
WGK
WGK 2
Flash Point (°F)
151.7 °F - closed cup
Flash Point (°C)
66.5 °C - closed cup
PPE (personal protective equipment)
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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