2-Oxa-6-azaspiro[3.3]heptane
[CAS# 174-78-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate
• Name: 2-Oxa-6-azaspiro[3.3]heptane
• Molecular Formula: C₅H₉NO
• Molecular Weight: 99.13
• CAS Registry Number: 174-78-7
• EC Number: 833-759-9
• SMILES: C1C2(CN1)COC2

Properties

• Density: 1.12
• Boiling point: 166 °C
• Flash point: 51 °C

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Risk Statements: H226-H315-H319
• Safety Statements: P210-P233-P240-P241-P242-P243-P264-P264+P265-P280-P302+P352-P303+P361+P353-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P235-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Flammable liquids	Flam. Liq.	3	H226

• Transport Information: UN 1993

Discovery and Applications

2-Oxa-6-azaspiro[3.3]heptane, also known as oxaspiroheptane, is a unique bicyclic compound with significant applications in medicinal chemistry and drug discovery. Its unique spirocyclic structure provides a rigid and constrained framework, making it a valuable scaffold in drug development. The spirocyclic structure of 2-oxa-6-azaspiro[3.3]heptane stems from advances in heterocyclic chemistry and the exploration of the biological activities of spirocyclic compounds. Spirocyclic compounds have been studied since the early 20th century, and in recent decades, there has been a renewed interest in them due to their potential in drug design.

Its chemical structure has a spirocyclic framework, i.e., a bicyclic structure in which one atom (the spirocyclic center) is shared by two rings, contains an oxygen atom as part of a five-membered ring, and contains a nitrogen atom in a three-membered ring attached to an oxygen-containing ring. It is a colorless liquid or crystalline solid that is soluble in common organic solvents such as ethanol and ether; its solubility in water is limited.

2-Oxa-6-azaspiro[3.3]heptane can be used as a rigid scaffold to mimic the biologically active conformations of natural compounds. Its spirocyclic structure restricts rotational freedom, making it useful for designing ligands with high specificity for biological targets. The compound is used in the synthesis of a variety of drugs, including central nervous system (CNS) drugs, antimicrobial agents, and anti-inflammatory drugs. Its unique structure can enhance the pharmacokinetic properties and bioavailability of these drugs.

In organic synthesis, 2-oxa-6-azaspiro[3.3]heptane is a versatile building block for the construction of complex molecules. It can be functionalized at different positions to introduce a variety of substituents, thereby facilitating the development of new chemical entities. The rigid spirocyclic core of 2-oxa-6-azaspiro[3.3]heptane provides a chiral environment that can be exploited to create stereochemically pure compounds. This is particularly valuable in asymmetric synthesis and the development of chiral drugs.

The structural features of this compound can be used to design new agrochemicals that target specific pathways in pests and weeds. Its stability and ability to form biologically active conformations make it an attractive candidate for the development of environmentally friendly pesticides and herbicides.

In materials science, 2-Oxa-6-azaspiro[3.3]heptane can be incorporated into polymers and other materials to impart special properties such as rigidity, stability, and resistance to degradation. This makes it useful for making advanced materials for coatings, adhesives, and composites. Its unique structure can be used to design chemical sensors that interact with target molecules in a specific way.

The unique spirocyclic structure of 2-Oxa-6-azaspiro[3.3]heptane can be used for mechanistic studies to understand reaction pathways and the behavior of spirocyclic compounds under different conditions, which can help design more efficient synthetic methods and catalysts. Researchers explore the reactivity and potential of 2-Oxa-6-azaspiro[3.3]heptane in various chemical transformations, which can help discover new reactions and synthetic routes.

References

2010. Oxetanes in Drug Discovery: Structural and Synthetic Insights. Journal of Medicinal Chemistry, 53(8).
DOI: 10.1021/jm9018788

2023. Proteolysis-targeting chimeras with reduced off-targets. Nature Chemistry, 16(3).
DOI: 10.1038/s41557-023-01379-8

2017. Synthesis and Properties of 2-Oxa-6-azaspiro[3.3]heptane Sulfonate Salts. Synthesis, 49(06).
DOI: 10.1055/s-0036-1588733