[3aS-(3aalpha,4alpha,5beta,6aalpha)]-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one
[CAS# 53275-53-9]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: [3aS-(3aalpha,4alpha,5beta,6aalpha)]-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one
• Synonyms: (3aS,4R,5S,6aR)-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28
• CAS Registry Number: 53275-53-9
• SMILES: C1[C@@H]2[C@@H](CC(=O)O2)[C@@H]([C@H]1OC(=O)C3=CC=CC=C3)CO

Properties

• Solubility: Very slightly soluble (0.94 g/L) (25 °C), Calc.^*
• Density: 1.33±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.588, Calc.^*
• Boiling Point: 481.9±30.0 °C (760 mmHg), Calc.^*
• Flash Point: 183.3±18.1 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319
• Safety Statements: P264-P280-P305+P351+P338-P337+P313

Discovery and Applications

[3aS-(3aalpha,4alpha,5beta,6aalpha)]-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one is a complex organic compound with unique structural features that position it as a valuable intermediate in synthetic organic chemistry. The compound belongs to the family of cyclopentafuran derivatives, characterized by a bicyclic structure that exhibits interesting reactivity patterns. Its discovery can be traced back to ongoing research into natural product synthesis and the exploration of bioactive molecules.

The synthesis of [3aS-(3aalpha,4alpha,5beta,6aalpha)]-5-(benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one involves multi-step organic reactions, often beginning with readily available starting materials that undergo cyclization and functionalization processes. Researchers have employed various strategies, including the use of protecting groups and selective reduction reactions, to achieve the desired stereochemistry and functional groups within the bicyclic framework. The hydroxymethyl group and the benzoyloxy substituent play significant roles in enhancing the compound's reactivity and solubility, making it suitable for further transformations.

One of the primary applications of this compound lies in its use as a building block for the synthesis of more complex natural products. The bicyclic structure, characterized by its fused ring system, allows for the construction of a diverse range of chemical entities through various synthetic methodologies. This flexibility has made it an attractive target for chemists engaged in the development of new therapeutic agents, particularly in the fields of oncology and anti-inflammatory research.

In pharmaceutical chemistry, [3aS-(3aalpha,4alpha,5beta,6aalpha)]-5-(benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one has been investigated for its potential bioactivity. The compound serves as a precursor to more complex molecules that exhibit promising biological properties, contributing to the ongoing search for novel drug candidates. The unique arrangement of functional groups within the bicyclic structure allows for the exploration of various interactions with biological targets, which is crucial in drug design.

Additionally, this compound can also find applications in materials science, where its chemical properties could be leveraged for the synthesis of new polymers or as additives in various formulations. The incorporation of the bicyclic structure into polymer matrices may lead to materials with improved mechanical properties or thermal stability, broadening the scope of its applicability beyond pharmaceuticals.

Overall, [3aS-(3aalpha,4alpha,5beta,6aalpha)]-5-(benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one represents a significant advancement in organic synthesis, highlighting the ongoing importance of complex molecular frameworks in the development of new chemical entities with potential applications across multiple disciplines.

References

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