1,4-Dioxaspiro[4.5]decan-8-one
[CAS# 4746-97-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty ketone (including enol)
• Name: 1,4-Dioxaspiro[4.5]decan-8-one
• Synonyms: 1,4-Cyclohexanedione monoethyleneacetal
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.18
• CAS Registry Number: 4746-97-8
• EC Number: 610-352-2
• SMILES: C1CC2(CCC1=O)OCCO2

Properties

• Melting point: 70-76 °C
• Boiling point: 125-128 °C (12 Hgmm)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

1,4-Dioxaspiro[4.5]decan-8-one is an interesting compound with a unique spirocyclic structure that has attracted much attention in synthetic chemistry and various industrial applications. The compound was discovered through an innovative approach to the synthesis of spirocyclic compounds and has a spirocyclic linker in which the 1,4-dioxane ring and the cyclohexane ring share a carbon atom and a ketone functional group at the eighth position.

The synthesis of 1,4-dioxaspiro[4.5]decan-8-one involves a cyclization reaction in which precursors such as diols and carbonyl compounds combine under specific conditions to form a spirocyclic skeleton. This process usually employs catalytic methods or specific reagents to promote the formation of the spirocyclic bond, highlighting the complexity of the synthesis of spirocyclic compounds.

1,4-Dioxaspiro[4.5]decan-8-one has valuable application value in the field of organic synthesis due to its stability and reactivity. Its spirocyclic structure gives it unique stereo and electronic properties, making it a versatile intermediate for the construction of complex molecules. One notable application is its use as a building block for drug synthesis, where the spirocyclic structure can promote the biological activity and stability of the target compound.

In addition, the compound is used to develop novel materials. The presence of the dioxane ring and keto group provides multiple sites for chemical modification, enabling the creation of polymers and resins with tailored properties. These materials can be used in coatings, adhesives, and other industrial applications that require specific mechanical and chemical properties.

1,4-Dioxaspiro[4.5]decan-8-one also plays a role in the synthesis of natural products and agrochemicals. The ability to introduce spirocyclic motifs into larger molecules is valuable for mimicking the structure of bioactive natural compounds, potentially developing new effective agents for agricultural and medicinal uses.

As research on spirocyclic compounds and their applications continues to deepen, 1,4-Dioxaspiro[4.5]decan-8-one remains a compound of interest. Its versatile reactivity and structural properties make it key to advancing synthetic methods and developing new materials and drugs.

References

2019. FR901483: Synthetic Efficiency Remains a Challenge. Synthesis, 51.
DOI: 10.1055/s-0037-1611779

2016. Recent Advances on Asymmetric Nitroso Aldol Reaction. Synthesis, 48.
DOI: 10.1055/s-0035-1561505

2015. Stereoselective Reactions in Preparation of Chiral α-Heteraspiro[m.n]alkanes. Synthesis, 47.
DOI: 10.1055/s-0034-1378863