(+/-)-Corey lactone 5-(4-phenylbenzoate)
[CAS# 54382-73-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ester intermediate
• Name: (+/-)-Corey lactone 5-(4-phenylbenzoate)
• Synonyms: (3aR,4S,5R,6aS)-Hexahydro-4-hydroxymethyl-5-(4-phenylbenzyloxy)cyclopenta[b]furan-2-one
• Molecular Formula: C₂₁H₂₀O₅
• Molecular Weight: 352.38
• CAS Registry Number: 54382-73-9
• SMILES: C1C2C(CC(=O)O2)C(C1OC(=O)C3=CC=C(C=C3)C4=CC=CC=C4)CO

Properties

• Density: 1.32
• Melting point: 134-136 °C

Safety Data

• Hazard Symbols: GHS09 Warning
• Risk Statements: H410
• Safety Statements: P273-P391-P501

Discovery and Applications

(+/-)-Corey lactone 5-(4-phenylbenzoate) is a synthetic organic compound notable for its complex structure and potential applications in medicinal chemistry. This compound is derived from the Corey lactone framework, a class of molecules recognized for their diverse biological activities and roles in natural product synthesis. The discovery of this compound is linked to ongoing research efforts aimed at exploring the therapeutic potential of lactone derivatives.

The initial synthesis of Corey lactones can be traced back to the groundbreaking work of Elias J. Corey, who developed a series of synthetic methodologies for constructing these cyclic esters in the 1960s. Corey’s innovative approaches to organic synthesis provided chemists with powerful tools to assemble complex molecular architectures, including those found in natural products. The introduction of substituents such as the 4-phenylbenzoate moiety to the Corey lactone structure further expanded its potential applications, making it a subject of interest in subsequent research.

The synthesis of (+/-)-Corey lactone 5-(4-phenylbenzoate) typically involves multi-step organic reactions, beginning with the appropriate lactone precursor. Key steps may include acylation reactions to introduce the 4-phenylbenzoate group, followed by purification processes to isolate the desired compound in its racemic form. The presence of both enantiomers in the final product can be advantageous, as it allows for the evaluation of their individual biological activities and potential therapeutic benefits.

One of the main applications of (+/-)-Corey lactone 5-(4-phenylbenzoate) lies in its use as an intermediate in the synthesis of more complex pharmaceutical compounds. The structural features of the lactone and the phenylbenzoate group enable further functionalization, which can lead to the development of new drug candidates targeting various diseases. The compound’s unique reactivity profile has made it a valuable scaffold in medicinal chemistry, particularly in the search for novel anticancer agents and anti-inflammatory drugs.

Moreover, the compound has shown potential in materials science, where its chemical properties could be exploited for the development of new polymers or coatings. The incorporation of Corey lactone derivatives into polymeric materials may enhance their mechanical properties or improve their resistance to environmental factors, making them suitable for a variety of applications.

Overall, (+/-)-Corey lactone 5-(4-phenylbenzoate) exemplifies the continued interest in lactone chemistry and its applications in both pharmaceuticals and materials science. Its unique structural characteristics and the ability to undergo further chemical transformations position it as a valuable compound for researchers exploring new avenues in synthetic chemistry.

References

2023. Multimodal action of KRP203 on phosphoinositide kinases in vitro and in cells. Biochemical and Biophysical Research Communications.
DOI: 10.1016/j.bbrc.2023.08.050

2022. Discovery of small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase. Journal of Enzyme Inhibition and Medicinal Chemistry.
DOI: 10.1080/14756366.2022.2070909

2014. A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum. Journal of biomolecular screening.
DOI: 10.1177/1087057114528738