(S)-(-)-Di-(2-naphthyl)-2-pyrrolidinemethanol - CAS 127986-84-9

(S)-(-)-Di-(2-naphthyl)-2-pyrrolidinemethanol is a proline-based organocatalyst that has been investigated for several powerful asymmetric transformations, such as the Aldol, Mannich, and Michael reactions.

Catalog Number

127986-84-9

CAS

127986-84-9

IUPAC Name

dinaphthalen-2-yl-[(2S)-pyrrolidin-2-yl]methanol

Synonyms

(S)-(-)-ALPHA,ALPHA-DI(2-NAPHTHYL)-2-PYRROLIDINEMETHANOL; (S)-(-)-ALPHA,ALPHA-DI(2-NAPTHYL)-2-PYRROLIDINEMETHANOL; (S)-(-)-DI-(2-NAPHTHYL)-2-PYRROLIDINEMETHANOL; (S)-DI-2-NAPHTHYLPROLINOL; (S)-DI-2-NAPHTHYLPROLINOL 99%; (S)-(-)-A,A-DI(2-NAPHTHYL)-2-PYRROLIDIN

Molecular Weight

353.46

Molecular Formula

C25H23NO

Product Information

Canonical SMILES

C1CC(NC1)C(C2=CC3=CC=CC=C3C=C2)(C4=CC5=CC=CC=C5C=C4)O

InChI

InChI=1S/C25H23NO/c27-25(24-10-5-15-26-24,22-13-11-18-6-1-3-8-20(18)16-22)23-14-12-19-7-2-4-9-21(19)17-23/h1-4,6-9,11-14,16-17,24,26-27H,5,10,15H2/t24-/m0/s1

InChI Key

LNUDNNFEXRHHGY-DEOSSOPVSA-N

Purity

95%

MDL

MFCD00269672

Appearance

white to light yellow crystal powder

Boiling Point

528.2°C at 760mmHg

Melting Point

138-143°C

Density

1.207g/cm3

Optical Activity

-98.0°( c = 1 in methanol)

WGK Germany

Safety Information

Signal Word

Warning

Precautionary Statement

P273 - P301+P312+P330 - P302+P352 - P305+P351+P338

Hazard Statements

H302 - H315 - H319 - H335 - H413

Reference Reading

1.(S)-(-)-alpha,alpha-Di(2-naphthyl)-2-pyrrolidinemethanol, a useful tool to study the recognition mechanism in chiral ligand-exchange chromatography.

Natalini B1, Sardella R, Macchiarulo A, Natalini S, Pellicciari R. J Sep Sci. 2007 Jan;30(1):21-7.

A dynamic coating of the RP-18 carbon chain layers with the new chiral selector (S)-(-)-alpha,alpha-di(2-naphthyl)-2-pyrrolidinemethanol allowed the formation of a mixed chiral stationary phase that has been used in the separation of a selected set of amino acid racemates. Both a representative model and classification structure-property relationship studies have been performed in order to study the contribution of hydrophobic, bulky and electron-donating groups in the side chain of the chiral selector to the mechanism of chiral recognition.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass