(2R)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl}pyrrolidine

• ChemBase ID: 140920
• Molecular Formular: C24H23F12NOSi
• Molecular Mass: 597.5118584
• Monoisotopic Mass: 597.13572953
• SMILES: C[Si](C)(C)OC(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)[C@H]1CCCN1
• Canonical SMILES: C[Si](OC(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)[C@H]1CCCN1)(C)C
• InChI: InChI=1S/C24H23F12NOSi/c1-39(2,3)38-20(19-5-4-6-37-19,13-7-15(21(25,26)27)11-16(8-13)22(28,29)30)14-9-17(23(31,32)33)12-18(10-14)24(34,35)36/h7-12,19,37H,4-6H2,1-3H3/t19-/m1/s1
• InChIKey: MOHRGTBNEJKFMB-LJQANCHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl}pyrrolidine
• IUPAC Traditional name: (2R)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl}pyrrolidine
• Synonyms: (R)-2-(Bis(3,5-bis(trifluoromethyl)phenyl)((trimethylsilyl)oxy)methyl)pyrrolidine; (R)-α,α-Bis[3,5-bis(trifluoromethyl)phenyl]prolinol trimethylsilyl ether; (R)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)]trimethylsilanyloxy)methyl]pyrrolidine; (R)-2-[(Bis(3,5-bis(trifluoromethyl)phenyl)]trimethylsilyloxy)methyl]pyrrolidine; (R)-α,α-Bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether; (R)-α,α-双[3,5-双(三氟甲基)苯基]脯氨醇三甲基硅醚; (R)-2-[(双(3,5-双(三氟甲基)苯基)]三甲基甲硅氧基)甲基]吡咯烷; (R)-2-[(双(3,5-双(三氟甲基)苯基)]三甲基硅烷氧基)甲基]吡咯烷; (R)-α,α-双[3,5-双(三氟甲基)苯基]-2-吡咯烷甲醇三甲基硅基醚

Database IDs

• CAS Number: 908303-26-4
• MDL Number: MFCD09750448
• PubChem SID: 162235158; 24885357
• PubChem CID: 16218311

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.9587817
• LogD (pH = 7.4): 6.0725293
• Log P: 8.4935
• Molar Refractivity: 117.2036 cm^3
• Polarizability: 44.21967 Å^3
• Polar Surface Area: 21.26 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 46-55 °C
• Flash Point: >110 °C; >230 °F

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95+%
• Grade: technical grade
• Optical Purity: enantiomeric excess: ≥99.0% (HPLC)
• Empirical Formula (Hill Notation): C24H23F12NOSi

DETAILS

Sigma Aldrich - 677213

Packaging
1, 5 g in glass bottle
Application
Catalyst involved in:
• Cyclocondensation of enals with methylenepyrrolidines1
• Organocatalytic additions of β-ketosulfoxides to conjugated aldehydes2
• Organocatalytic aza-Michael reactions3,4
• Stereoselective propargylic alkylation of propargylic esters with aldehydes5
• Epoxidation or aziridination of α,β-unsaturated aldehydes and Feist-Benary reactions of 1,3-dicarbonyls6
Protocols & Applications
Asymmetric a-Functionalization of Aldehydes using J?rgensen's Organocatalysts