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273112

Sigma-Aldrich

(1R,E)-(+)-Camphorquinone 3-oxime

99%

Synonym(s):

(1R,E)-(+)-2,3-Bornanedione 3-oxime, anti-(1R)-(+)-Camphorquinone 3-oxime

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About This Item

Empirical Formula (Hill Notation):
C10H15NO2
CAS Number:
31571-14-9
Molecular Weight:
181.23
Beilstein/REAXYS Number:
3200377
MDL number:
MFCD00074848
UNSPSC Code:
12352115
PubChem Substance ID:
24856531
NACRES:
NA.22

assay

99%

form

solid

optical activity

[α]25/D +200°, c = 1 in ethanol

mp

153-156 °C (lit.)

SMILES string

[H][C@@]12CC[C@@](C)(C(=O)\C1=N/O)C2(C)C

InChI

1S/C10H15NO2/c1-9(2)6-4-5-10(9,3)8(12)7(6)11-13/h6,13H,4-5H2,1-3H3/b11-7-/t6-,10+/m1/s1

InChI key

YRNPDSREMSMKIY-HAKKTOSXSA-N

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Application

(1R,E)-(+)-Camphorquinone 3-oxime can be used to prepare chiral camphor-oxazoline auxiliary, which is used to blend diastereoselectivity and isomer separability for the efficient synthesis of bicuculline, egenine, corlumine, and corytensine.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

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1-Magnesiotetrahydroisoquinolyloxazolines as Chiral Nucleophiles in Stereoselective Additions to Aldehydes: Auxiliary Optimization, Asymmetric Synthesis of (+)-Corlumine,(+)-Bicuculline,(+)-Egenine, and (+)-Corytensine, and Preliminary 13C NMR Studies of 1-Lithio-and 1-Magnesiotetrahydroisoquinolyloxazolines
Gawley RE and Z Pingsheng
The Journal of Organic Chemistry, 61(23), 8103- 8112 (1996)

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