(R)-(-)-3-Hydroxytetrahydrofuran
(R)-(-)-3-Hydroxytetrahydrofuran is a chiral compound with a hydroxyl group (-OH) attached to the third carbon of a tetrahydrofuran ring. The “(R)” designation indicates the absolute configuration of the chiral center at the 3-position, while “(-)” refers to the optical rotation, meaning the compound rotates plane-polarized light to the left (levorotatory).
Key Features:
- Structure: Tetrahydrofuran (THF) is a five-membered ring with one oxygen atom. In this compound, a hydroxyl group is attached to the 3-position of the ring.
- Chirality: The 3-position carbon is a stereocenter, making the molecule chiral. The (R) configuration is determined by the Cahn-Ingold-Prelog priority rules.
- Optical Activity: The (-) sign indicates that the compound is levorotatory, meaning it rotates plane-polarized light counterclockwise.
Applications:
- Synthetic Intermediate: It is often used as a building block in organic synthesis, particularly in the preparation of pharmaceuticals and fine chemicals.
- Chiral Auxiliary: Its chiral nature makes it useful in asymmetric synthesis to induce stereoselectivity in reactions.
Properties:
- Molecular Formula: C₄H₈O₂
- Boiling Point: Varies depending on the exact structure and substituents.
- Solubility: Likely soluble in polar solvents like water, alcohols, and ethers due to the presence of the hydroxyl group.
Synthesis:
It can be synthesized through various methods, such as:
- Reduction of corresponding lactones or esters.
- Asymmetric hydrogenation of furan derivatives.
If you need more specific information, such as synthesis routes or applications, feel free to ask!
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