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Key Documents

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276286

Sigma-Aldrich

(1R)-(−)-Camphorquinone

99%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C10H14O2
Número de CAS:
10334-26-6
Peso molecular:
166.22
Beilstein/REAXYS Number:
2327696
MDL number:
MFCD00082863
UNSPSC Code:
12352115
PubChem Substance ID:
24856697
NACRES:
NA.22

Quality Level

100

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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Categorías relacionadas

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

Exclamation markHealth hazard
GHS07,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Resp. Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificados de análisis (COA)

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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)
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
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
Tetrahedron Asymmetry, 17, 1179-1179 (2006)
Jan Hintzpeter et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 29(1), 263-273 (2014-11-08)
The purpose of this study was to investigate the origin and function of the aldo-keto reductase (AKR) superfamily as enzymes involved in the detoxification of xenobiotics. We used the cyanobacterium Synechocystis sp. PCC 6803 as a model organism and sequence

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