196436

(1R)-(−)-Fenchone

≥98%

• 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: 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

Properties

• 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.)
• 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

Description

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.

Safety Information

• Pictograms: 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