420964

(1S)-(+)-Ketopinic acid

99%

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

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315 - H319 - H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves