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420964

Sigma-Aldrich

(1S)-(+)-Ketopinic acid

99%

Synonym(s):

(1S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H14O3
CAS Number:
40724-67-2
Molecular Weight:
182.22
Beilstein:
4180005
MDL number:
MFCD00168053
UNSPSC Code:
12352115
PubChem Substance ID:
24866367
NACRES:
NA.22

Assay

99%

optical activity

[α]23/D +58°, c = 1 in chloroform

mp

237-239 °C (lit.)

SMILES string

CC1(C)C2CCC1(C(O)=O)C(=O)C2

InChI

1S/C10H14O3/c1-9(2)6-3-4-10(9,8(12)13)7(11)5-6/h6H,3-5H2,1-2H3,(H,12,13)/t6-,10+/m1/s1

InChI key

WDODWBQJVMBHCO-LDWIPMOCSA-N

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General description

(1S)-(+)-Ketopinic acid is a chiral ketone.

Application

(1S)-(+)-Ketopinic acid may be used to prepare:
  • Chiral phosphine-oxazoline ligands, which can used in asymmetric palladium-catalyzed Heck reaction of aryl or alkenyl triflates with cyclic alkenes.
  • A chiral imino-phosphine ligand, which can be used in palladium-catalyzed asymmetric Diels–Alder reactions to prepare six-membered carbocycles.
  • A chiral iminopyridine ligand, which can be used in copper-catalyzed Henry (nitro aldol) reaction between nitromethane and o-anisol to form the corresponding β-hydroxynitroalkane.
Used to prepare a new chiral oxazolidone auxiliary and a ketopinic derivatized polymer used for the deracemization of amines. Starting material for the synthesis of homochiral 2,10-camphanediols. Employed in the formation of a chiral Schiff base precursor to diethyl (S)-α-amino-α-alkyl phosphonates.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Palladium-catalyzed asymmetric Diels-Alder reactions with novel chiral imino-phosphine ligands.
Hiroi K and Watanabe K.
Tetrahedron Asymmetry, 12(22), 3067-3071 (2001)
Calmes, M. et al.
Tetrahedron Asymmetry, 5, 817-817 (1994)
Chiral P, N-ligands based on ketopinic acid in the asymmetric Heck reaction.
Gilbertson SR and Fu Z.
Organic Letters, 3(2), 161-164 (2001)
Modular iminopyridine ligands. Application to the enantioselective copper (II)-catalyzed Henry reaction.
Blay G, et al.
Tetrahedron Asymmetry, 17(14), 2046-2049 (2006)
M. Ferrari et al.
Synthetic Communications, 22, 107-107 (1992)
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