(S,S)-(-)-Hydrobenzoin
(S,S)-(-)-Hydrobenzoin is a specific stereoisomer of hydrobenzoin, which is a diol derived from benzoin. The compound has two chiral centers, leading to multiple stereoisomers, including (S,S)-(-)-Hydrobenzoin and its enantiomer (R,R)-(+)-Hydrobenzoin.
Key Features:
- Chemical Structure:
- It has the molecular formula ( C_{14}H_{14}O_2 ).
- It consists of two phenyl groups attached to a central ethane-1,2-diol backbone.
- Stereochemistry:
- The (S,S) designation indicates that both chiral centers have the S-configuration.
- The (-) sign indicates that this enantiomer is levorotatory, meaning it rotates plane-polarized light to the left.
- Synthesis:
- (S,S)-(-)-Hydrobenzoin can be synthesized through the asymmetric reduction of benzoin or its derivatives using chiral catalysts or reagents.
- Applications:
- It is often used in organic synthesis as a chiral building block.
- It can serve as a ligand in asymmetric catalysis.
- It is also used in the study of stereochemistry and chiral resolution.
- Physical Properties:
- It is typically a white crystalline solid.
- It has specific melting points and optical rotation values that can be used for identification.
Example Reaction:
One common method to synthesize (S,S)-(-)-Hydrobenzoin is through the asymmetric hydrogenation of benzoin using a chiral catalyst like (R)-BINAP-Ru complex.
[ \text{Benzoin} + \text{H}_2 \xrightarrow{\text{Chiral Catalyst}} (S,S)-(-)-\text{Hydrobenzoin} ]
Importance:
The study and use of (S,S)-(-)-Hydrobenzoin are significant in the field of asymmetric synthesis and chiral chemistry, where the control of stereochemistry is crucial for the production of enantiomerically pure compounds, which are important in pharmaceuticals, agrochemicals, and materials science.
If you need more detailed information or specific reactions involving (S,S)-(-)-Hydrobenzoin, feel free to ask!
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