420964
(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:
Molecular Weight:
182.22
UNSPSC Code:
12352115
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4180005
Assay:
99%
Quality Segment
assay
99%
optical activity
[α]23/D +58°, c = 1 in chloroform
mp
237-239 °C (lit.)
functional group
carboxylic acid, ketone
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
General description
(1S)-(+)-Ketopinic acid is a chiral ketone.
Application
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.
(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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
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