420964

(1S)-(+)-Ketopinic acid

99%

• Synonyme(s) : (1S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid
• Formule empirique (notation de Hill): C₁₀H₁₄O₃
• Numéro CAS: 40724-67-2
• Poids moléculaire : 182.22
• Numéro Beilstein : 4180005
• Numéro MDL: MFCD00168053
• Code UNSPSC : 12352115
• ID de substance PubChem : 24866367
• Nomenclature NACRES : NA.22

Propriétés

• Pureté: 99%
• Activité optique: [α]23/D +58°, c = 1 in chloroform
• Pf: 237-239 °C (lit.)
• Groupe fonctionnel: carboxylic acid; ketone
• Chaîne SMILES: 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
• Clé InChI: WDODWBQJVMBHCO-LDWIPMOCSA-N

Description

Description générale

(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.

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H315,H319,H335
• Conseils de prudence: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Classification des risques: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Organes cibles: Respiratory system
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Gloves