(R)-Di-2-Naphthylprolinol, CAS No. 130798-48-0

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130798-48-0

Catalog No. EBD40589

CAS 130798-48-0

Name (R)-Di-2-Naphthylprolinol

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Basic Information

Synonyms: (r)-(+)-di-(2-naphthyl)-2-pyrrolidinemethanol (r)-(+)-alpha,alpha-di(2-naphthyl)-2-pyrrolidinemethanol (r)-(+)-2-[bis-(2-naphthyl)-hydroxymethyl]-pyrrolidin (r)-(+)-a,a-di(2-napthyl)-2-pyrrolidinemethanol (r)-di-2-naphthylproline. (r)-di-2-naphthylprolinol99% (r)-(+)-α,α-di(2-napthyl)-2-pyrrolidinemethanol (R)-DI-2-NAPHTHYLPROLINOL dinaphthalen-2-yl[(2R)-pyrrolidin-2-yl]methanol dinaphthalen-2-yl[

Molecular Formula: C25H23NO

Molecular Weight: 353.46

MDL Number: MFCD00274637

Categories: Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

(R)-Diphenylprolinol, also known as (R)-2-(diphenylmethyl)pyrrolidine, is a chiral amine compound. It is a white to off-white crystalline powder with the molecular formula C17H19N. This compound is a key derivative of proline and serves as a versatile chiral building block and ligand in organic synthesis. Its primary and most significant application is as a chiral organocatalyst, particularly in asymmetric synthesis. It is widely used to catalyze a variety of enantioselective reactions, including Michael additions, aldol reactions, and α-functionalizations of carbonyl compounds. The catalyst is often employed in its silylated form (e.g., TMS-protected) to enhance its reactivity and selectivity. Its effectiveness stems from its ability to form reactive enamine or iminium ion intermediates with carbonyl substrates, facilitating stereocontrolled bond formation. Due to its efficiency, commercial availability, and broad utility in constructing chiral centers, (R)-diphenylprolinol is a fundamental tool in medicinal chemistry and pharmaceutical research for the synthesis of enantiomerically pure drug candidates and natural products.

Physical Properties

Melting Point: 135-138 °C (lit.)

Boiling Point: 528.2 °C at 760 mmHg

Flash Point: 129.2 °C

Density: 1.207 g/cm3

Analytical Data

Appearance: white to light yellow crystal powder