(R)-1-Phenylethanol
(R)-1-Phenylethanol is a chiral secondary alcohol with the molecular formula C₈H₁₀O. It consists of a phenyl group attached to an ethanol backbone, with the hydroxyl group (–OH) on the chiral center. The (R) designation indicates the specific spatial arrangement of the atoms around the chiral center, following the Cahn-Ingold-Prelog priority rules.
Key Features:
- Structure:
- Phenyl group (C₆H₅) attached to the first carbon of ethanol.
- Chiral center at the carbon bearing the hydroxyl group (–OH) and the phenyl group.
- The (R) configuration means the substituents are arranged in a clockwise order of priority (OH > C₆H₅ > CH₃ > H).
- Physical Properties:
- Appearance: Colorless liquid.
- Boiling point: ~204–205°C.
- Optical activity: It is optically active due to the chiral center.
- Synthesis:
- Can be prepared via asymmetric reduction of acetophenone using chiral catalysts or enzymes.
- Alternatively, it can be synthesized via resolution of racemic 1-phenylethanol.
- Applications:
- Used as a chiral building block in organic synthesis.
- Employed in the production of pharmaceuticals, fragrances, and fine chemicals.
- Enantiomeric Form:
- The (S)-1-Phenylethanol is the enantiomer of (R)-1-Phenylethanol, with opposite optical rotation and spatial arrangement.
Example Reaction:
(R)-1-Phenylethanol can be oxidized to form acetophenone using oxidizing agents like PCC (Pyridinium chlorochromate):
[
\text{(R)-1-Phenylethanol} \xrightarrow{\text{PCC}} \text{Acetophenone}
]
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