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Merck
CN

276286

(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
UNSPSC Code:
12352115
NACRES:
NA.22
PubChem Substance ID:
24856697
MDL number:
MFCD00082863
Beilstein/REAXYS Number:
2327696

Key Documents

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Product Name

(1R)-(−)-Camphorquinone, 99%

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

SMILES string

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

InChI key

VNQXSTWCDUXYEZ-LDWIPMOCSA-N

assay

99%

optical activity

[α]20/D −101°, c = 2 in toluene

mp

200-203 °C (lit.)

functional group

ketone

Quality Level

100

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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

signalword

Danger

hcodes

H302,H334

Hazard Classifications

Acute Tox. 4 Oral - Resp. Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ0987
STBD1108V
02004BV
06021PD
09222PD

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Stereoselective reduction of ketones by various vegetables
Utsukihara T, et al.
Journal of Molecular Catalysis. B, Enzymatic, 41(3-4), 103-109 (2006)
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
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)
Synthesis of camphoric anhydride via unsensitized photo-oxidation of camphorquinone
Shun-Jun J, et al.
Synthetic Communications, 32(11), 1659-1663 (2002)
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