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D(-)-Prolinol is the unnatural enantiomer (mirror-image) of the amino alcohol derived from proline. Its structure features a pyrrolidine ring (5-membered N-heterocycle) with a hydroxymethyl group (-CH₂OH) attached. The "D(-)" designation specifies its chirality (D-configuration) and levorotatory optical activity.
Key Uses:
Chiral Building Block: Widely employed in asymmetric synthesis as a versatile precursor or auxiliary due to its rigid, stereodefined scaffold.
Bifunctional Catalyst/Ligand: Its secondary amine and alcohol groups enable use in organocatalysis or as ligands for metal-catalyzed reactions.
Applications: Critical for synthesizing chiral pharmaceuticals, agrochemicals, and complex natural products.
In short: A valuable, non-natural chiral tool in organic chemistry.
D(-)-Prolinol is a chiral, non-proteinogenic amino alcohol with the following key characteristics:
Chemical Structure:
Derived from the amino acid proline (specifically its unnatural D-enantiomer).
Contains a pyrrolidine ring (5-membered nitrogen heterocycle) with a hydroxymethyl group (-CH₂OH) replacing proline's carboxylic acid.
Stereochemistry: The "D(-)" designation indicates it is the D-enantiomer (mirror image) of naturally occurring L-proline derivatives, and the "(-)" often refers to its levorotatory optical activity.
Key Features & Uses:
Chiral Building Block: Widely used in asymmetric synthesis as a chiral auxiliary, ligand, or catalyst due to its rigid structure and stereogenic center.
Bifunctional Reactivity: Combines a secondary amine (within the ring) and a primary alcohol, enabling diverse derivatization.
Applications: Crucial for synthesizing pharmaceuticals, agrochemicals, and chiral catalysts (e.g., for organocatalysis or transition metal complexes). Also used in peptidomimetics and material science.
Properties:
Typically a colorless to pale yellow liquid.
CAS Number: 68832-13-3.
Safety: Flammable, corrosive, and harmful; requires careful handling.
In short: D(-)-Prolinol is the D-enantiomer of prolinol, valued primarily as a versatile chiral scaffold in asymmetric organic synthesis and catalysis.
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