中国|杭州|桐庐|蜂竞生物fenjinbio.com| 联系：17767155726，E-mail：和网络726@163.co’m(S,S)-1,2-Diphenylethane-1,2-diol, also known as (S,S)-hydrobenzoin, is an organic compound with the molecular formula C₁₄H₁₄O₂. It is a chiral diol, meaning it has two hydroxyl (-OH) groups attached to a 1,2-diphenylethane backbone, and it exists in the (S,S) enantiomeric form. Here are some key points about this compound:
Structure:
- The molecule consists of two phenyl groups (C₆comH₅) attached to a central ethane (C₂H₄) backbone.
- Each of the two central carbon atoms in the ethane backbone is bonded to a hydroxyl group (-OH).
- The (S,S) designation indicates that both chiral centers have the S-configuration, meaning the substituents around each chiral carbon are arranged in a specific spatial orientation.
Properties:
- Chirality: The presence of two chiral centers gives rise to stereoisomers. The (S,S) form is one of the possible enantiomers.
- Optical Activity: As a chiral molecule, (S,S)-1,2-Diphenylethane-1,2-diol is optically active and can rotate plane-polarized light.
- Melting Point: The compound typically has a well-defined melting point, which can vary slightly depending on purity.
- Solubility: It is generally soluble in organic solvents like ethanol, methanol, and acetone but less soluble in water.
Synthesis:
- (S,S)-1,2-Diphenylethane-1,2-diol can be synthesized via the asymmetric reduction of benzil (1,2-diphenylethane-1,2-dione) using chiral catalysts or reagents.
- Enzymatic reduction methods using specific dehydrogenases or baker’s yeast can also yield the (S,S)-enantiomer selectively.
Applications:
- Chiral Auxiliary: It is used in asymmetric synthesis as a chiral building block or auxiliary.
- Ligand in Catalysis: The diol can serve as a ligand in chiral catalysts for enantioselective reactions.
- Pharmaceuticals: Chiral diols like this are often intermediates in the synthesis of biologically active compounds.
Stereochemistry:
- The (S,S) enantiomer is one of four possible stereoisomers: (S,S), (R,R), (R,S), and (S,R). The (R,R) form is its enantiomer, while the (R,S) and (S,R) forms are diastereomers.
If you need more specific information, such as reaction mechanisms or spectroscopic data, feel free to ask!