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327956

Sigma-Aldrich

(1R)-(+)-Nopinone

98%

Synonym(s):

6,6-Dimethylbicyclo[3.1.1]heptan-2-one

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About This Item

Empirical Formula (Hill Notation):
C9H14O
CAS Number:
38651-65-9
Molecular Weight:
138.21
MDL number:
MFCD08447116
UNSPSC Code:
12352115
PubChem Substance ID:
24859704
NACRES:
NA.22

Assay

98%

form

liquid

optical activity

[α]20/D +16°, neat

refractive index

n20/D 1.479 (lit.)

bp

209 °C (lit.)

density

0.981 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C9H14O/c1-9(2)6-3-4-8(10)7(9)5-6/h6-7H,3-5H2,1-2H3/t6-,7-/m0/s1

InChI key

XZFDKWMYCUEKSS-BQBZGAKWSA-N

Related Categories

Application

(1R)-(+)-Nopinone may be used in the preparation of a chiral annulated indene derivative, which can be a potentially useful chiral ligand for transition metal complexes in asymmetric transformations. It may also react with secondary amines in cyclohexane to form the corresponding enamines.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

167.0 °F - closed cup

Flash Point(C)

75 °C - closed cup

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 (1R)-(+)-nopinone-and (1S)-(-)-verbenone-derived chiral annulated indenes via electrocyclic reactions.
Liu C and Sowa JR.
Tetrahedron Letters, 37(40), 7241-7244 (1996)
Boranes in synthesis-VII. Synthesis of 2-dialkylamino-6, 6-dimethylbicyclo [3.1. 1] heptan-3-ols from (R)-(+)-nopinone. Chiral auxiliaries for the addition of diethylzinc to aromatic aldehydes.
Goralski CT, et al.
Tetrahedron Asymmetry, 8(23), 3863-3871 (1997)

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