2-Oxa-6-azaspiro[3.3]heptane ethanedioate
[CAS# 1159599-99-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 2-Oxa-6-azaspiro[3.3]heptane ethanedioate
• Synonyms: 2-Oxa-6-azaspiro[3.3]heptane oxalate
• Molecular Formula: C₅H₉NO.C₂H₂O₄
• Molecular Weight: 189.17
• CAS Registry Number: 1159599-99-1
• SMILES: C1C2(CN1)COC2.C(=O)(C(=O)O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P280-P305+P351+P338-P310

Discovery and Applications

2-Oxa-6-azaspiro[3.3]heptane oxalate, commonly known as 2-oxa-6-azaspiroheptane oxalate, is an interesting compound known for its spirocyclic structure and usefulness in pharmaceutical and material science. The discovery of 2-oxa-6-azaspiro[3.3]heptane oxalate dates back to the mid-20th century, and interest in spirocyclic compounds has grown due to their structural rigidity and conformational restrictions. Spirocyclic compounds are characterized by two non-adjacent rings sharing a single atom, providing unique opportunities for synthesis and medicinal chemistry.

The synthesis of 2-oxa-6-azaspiro[3.3]heptane oxalate typically involves multiple steps. The core structure 2-oxa-6-azaspiro[3.3]heptane is synthesized by cyclization of suitable precursors such as aziridine or oxirane. The free base of the spirocyclic compound is then reacted with oxalic acid to form the oxalate salt. This step enhances the stability and solubility of the compound, making it easier to handle and use in a variety of applications.

The chemical structure of 2-oxa-6-azaspiro[3.3]heptane oxalate has the following features: The spiro[3.3]heptane skeleton is a rigid bicyclic structure in which a single atom (carbon) serves as the connection point between the oxirane ring and the aziridine ring. The presence of oxygen and nitrogen in the ring system introduces functionality and reactivity that can be used for synthetic transformations. The oxalate form (oxalate) stabilizes the spirocyclic core, enhances solubility in polar solvents, and can affect the crystallization behavior of the compound.

2-oxa-6-azaspiro[3.3]heptane oxalate is used in the design and synthesis of pharmaceutical compounds. The spirocyclic core provides a rigid scaffold that imparts a specific spatial orientation to the pharmacophore, enhancing binding affinity and selectivity for biological targets. This structural motif is particularly valuable in the development of enzyme inhibitors, receptor ligands, and modulators of protein-protein interactions.

The oxalate form of this compound improves the solubility and stability of drug candidates, facilitating the formulation of drugs with better bioavailability and longer shelf life.

2-Oxa-6-azaspiro[3.3]heptane oxalate derivatives were screened for pharmacokinetic and pharmacodynamic properties during the lead compound optimization phase of drug development. Researchers modified the spirocyclic structure to enhance the desired biological activity, minimize toxicity, and improve overall drug properties.

Spirocyclic structures are versatile building blocks for the synthesis of more complex organic molecules. Their rigid framework can be used to construct a variety of molecular structures, including spiro-fused polycyclic systems, which are valuable in natural product synthesis and the development of new synthetic methods. The compound can be functionalized at various positions on the spirocyclic core, enabling the creation of a wide range of derivatives with customized properties. The oxirane and aziridine rings in 2-oxa-6-azaspiro[3.3]heptane provide reactive sites for ring-opening reactions. These reactions can introduce new functional groups or connect the spirocyclic core to other molecular frameworks, expanding the utility of the compound in synthetic applications.

Spirocyclic structures can be incorporated into polymer backbones to create materials with unique mechanical and thermal properties. These spirocyclic-containing polymers can be used in coatings, adhesives, and high-performance materials. In the field of molecular electronics, 2-oxa-6-azaspiro[3.3]heptane derivatives are being studied for their potential as building blocks for organic semiconductors and electronic devices. The rigidity and electronic properties of the spirocyclic core can improve the performance of organic electronic materials. The spirocyclic structure and reactive functional groups of the compound can be used to develop sensors for the detection of various analytes for environmental monitoring, chemical detection, and biosensing.

References

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