(2S)-2-(fluorodiphenylmethyl)pyrrolidine

• ChemBase ID: 150989
• Molecular Formular: C17H18FN
• Molecular Mass: 255.3299232
• Monoisotopic Mass: 255.1423278
• SMILES: c1ccc(cc1)C(c1ccccc1)([C@@H]1CCCN1)F
• Canonical SMILES: FC(c1ccccc1)(c1ccccc1)[C@@H]1CCCN1
• InChI: InChI=1S/C17H18FN/c18-17(16-12-7-13-19-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,19H,7,12-13H2/t16-/m0/s1
• InChIKey: PGKMVPFJFKOUDA-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(fluorodiphenylmethyl)pyrrolidine
• IUPAC Traditional name: (2S)-2-(fluorodiphenylmethyl)pyrrolidine
• Synonyms: (S)-(-)-2-(Fluorodiphenylmethyl)pyrrolidine; (S)-(-)-2-(氟二苯甲基)吡咯烷

Database IDs

• CAS Number: 274674-23-6
• MDL Number: MFCD03093547
• PubChem SID: 24879279; 162245148
• PubChem CID: 16217116

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.5979104
• LogD (pH = 7.4): 1.7104809
• Log P: 3.7674382
• Molar Refractivity: 75.4908 cm^3
• Polarizability: 29.611492 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 145.4 °F; 63 °C
• Density: 1.096 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.576(lit.)
• Optical Rotation: [α]/D -27°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 97%
• Optical Purity: ee: 98% (HPLC)
• Empirical Formula (Hill Notation): C17H18FN

DETAILS

Sigma Aldrich - 552569

Packaging
500 mg in glass bottle
Legal Information
A Product of Onyx Scientific, U.K.
Application
Features:
• Highly efficient
• Excellent enantioselectivities
• Available in both enantiomers
• Operationally simple transformationsCatalyst for the enantioselective Weitz-Scheffer epoxidation of α,β-unsaturated aldehydes.1Condensation of this secondary amine with an aldehyde reversibly generates a β-fluoroiminium species where the fluorine atom is positioned gauche to the electropositive nitrogen centre.2Consequently, the phenyl substituents on the fluorine bearing carbon are placed in a predictable region of space. One of the groups effectively shields the upper face of the pendant iminium chain.Addition of hydrogen peroxide occurs in a highly selective manner to furnish optically enriched epoxides with excellent levels of enantiocontrol (Scheme 1).Simple α,β-disubstituted enals such as trans-cinnamaldehyde are smoothly converted to the corresponding epoxy aldehydes (up to 96% ee) as are their aliphatic analogues. The enantioselective, catalytic epoxidation of more challenging cyclic α,α,β-trisubstituted enals, and even an example of a α,α,β,β-tetrasubstituted enal, proceed with good yields and excellent enantioselectivities (up to 98% ee)3 (Scheme 2).