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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:
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.)

functional group

ketone
oxime

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.[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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

273112-VAR:
273112-1G:
273112-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
STBB1930
13415HE
17603
S36559
14331AN

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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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