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(S)-(-)-2-(Fluorodiphenylmethyl)pyrrolidine_Molecular_structure_CAS_274674-23-6)
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(S)-(-)-2-(Fluorodiphenylmethyl)pyrrolidine

Catalog No. 552569 Name Sigma Aldrich
CAS Number 274674-23-6 Website http://www.sigmaaldrich.com
M. F. C17H18FN Telephone 1-800-521-8956
M. W. 255.3299232 Fax
Purity 97% Email
Storage Chembase ID: 150989

SYNONYMS

Title
(S)-(-)-2-(氟二苯甲基)吡咯烷
IUPAC name
(2S)-2-(fluorodiphenylmethyl)pyrrolidine
IUPAC Traditional name
(2S)-2-(fluorodiphenylmethyl)pyrrolidine

DATABASE IDS

PubChem SID 24879279
MDL Number MFCD03093547
CAS Number 274674-23-6

PROPERTIES

Empirical Formula (Hill Notation) C17H18FN
Optical Purity ee: 98% (HPLC)
Purity 97%
Density 1.096 g/mL at 25 °C(lit.)
Flash Point 63 °C
Flash Point 145.4 °F
Optical Rotation [α]/D -27°, c = 1 in chloroform
Refractive Index n20/D 1.576(lit.)
GHS Pictograms GHS07
GHS Signal Word Warning
GHS Hazard statements H315-H319-H335
European Hazard Symbols Irritant Irritant (Xi)
MSDS Link Download
Personal Protective Equipment Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
GHS Precautionary statements P261-P305 + P351 + P338
Risk Statements 36/37/38
Safety Statements 26-36
German water hazard class 3

DETAILS

Description (English)
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).
Description (简体中文)
包装
500 mg in glass bottle
Legal Information
英国 Onyx Scientific 产品
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).

REFERENCES