368199

(S)-(−)-α,α-Diphenyl-2-pyrrolidinemethanol

99%

• Synonyme(s) : (S)-(−)-2-(Diphenylhydroxymethyl)pyrrolidine, α,α-Diphenyl-L-prolinol
• Formule empirique (notation de Hill): C₁₇H₁₉NO
• Numéro CAS: 112068-01-6
• Poids moléculaire : 253.34
• Numéro MDL: MFCD00075506
• Code UNSPSC : 12352005
• ID de substance PubChem : 24862899
• Nomenclature NACRES : NA.22

Propriétés

• Pureté: 99%
• Forme: solid
• Activité optique: [α]20/D −67°, c = 3 in chloroform
• Pf: 77-80 °C (lit.)
• Groupe fonctionnel: hydroxyl; phenyl
• Chaîne SMILES: OC([C@@H]1CCCN1)(c2ccccc2)c3ccccc3
• InChI: 1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2/t16-/m0/s1
• Clé InChI: OGCGXUGBDJGFFY-INIZCTEOSA-N

Description

Description générale

(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol is a bifunctional organocatalyst.

Application

(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol (DPPM) may be used in the following processes:

• DPPM reacts with catecholborane to form a spiroborate ester, which can be an efficient catalyst for the synthesis of enantiopure alcohols by borane reduction of acetophenone.
• The catalyst generated in situ by reacting DPPM with borane-diethylaniline, can efficiently catalyze the enantioselective reduction of 2′-fluoroacetophenone.
• Mesoporous SBA-15 silica functionalized with DPPM can catalyze the addition of diethylzinc to benzaldehyde to form (S)-1-phenyl-propanol.

Used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones.

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
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Gloves