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Sigma-Aldrich

(1R)-(−)-Camphorquinone

99%

Synonym(s):

(1R)-(−)-2,3-Bornanedione, 2,3-Bornanedione

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About This Item

Empirical Formula (Hill Notation):
C10H14O2
CAS Number:
10334-26-6
Molecular Weight:
166.22
Beilstein:
2327696
MDL number:
MFCD00082863
UNSPSC Code:
12352115
PubChem Substance ID:
24856697
NACRES:
NA.22

Assay

99%

optical activity

[α]20/D −101°, c = 2 in toluene

mp

200-203 °C (lit.)

SMILES string

CC1(C)[C@@H]2CC[C@@]1(C)C(=O)C2=O

InChI

1S/C10H14O2/c1-9(2)6-4-5-10(9,3)8(12)7(6)11/h6H,4-5H2,1-3H3/t6-,10+/m1/s1

InChI key

VNQXSTWCDUXYEZ-LDWIPMOCSA-N

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Application

(1R)-(−)-Camphorquinone can be used as a chiral starting material for the preparation of:
  • α-Hydroxycamphors by selective reduction of keto groups using various vegetables.
  • Camphor-1,2-diamine platinum(II) complexes for DNA interaction studies.
  • Camphoric anhydride by unsensitized photo-oxidation in the presence of oxygen and polar solvents.
  • Camphorquinone-based chiral homoallylic amine, which is reacted with aldehydes to produce homoallylic primary amines via imine formation followed by 2-azonia-Cope rearrangement.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H334

Hazard Classifications

Acute Tox. 4 Oral - Resp. Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Synthesis of camphoric anhydride via unsensitized photo-oxidation of camphorquinone
Shun-Jun J, et al.
Synthetic Communications, 32(11), 1659-1663 (2002)
Angel M Montaña et al.
Bioorganic & medicinal chemistry, 16(4), 1721-1737 (2007-11-27)
The platinum(II) complex cis-[(1S,2R,3S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diamine]dichloroplatinum(II) (1) and its enantiomer (2) have been synthesized and physically and spectroscopically characterized. To obtain the enantiopure complexes the chiral pool approach was applied. The synthetic pathway has four steps, starting from (+/-)-diphenylethylenediamine (DPEDA) (3) and
Stereoselective reduction of ketones by various vegetables
Utsukihara T, et al.
Journal of Molecular Catalysis. B, Enzymatic, 41(3-4), 103-109 (2006)
Masaharu Sugiura et al.
Journal of the American Chemical Society, 128(34), 11038-11039 (2006-08-24)
A camphorquinone-derived chiral homoallylic amine was found to react with various aldehydes via imine formation and asymmetric 2-azonia-Cope rearrangement to give optically active homoallylic primary amines. A practical level of enantioselectivity with high functional group tolerance has been attained in
Tetrahedron Asymmetry, 17, 1179-1179 (2006)
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