3,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-9-one
[CAS# 69225-59-8]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 3,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-9-one
• Synonyms: 1,4-Cyclohexanedione mono(2,2-dimethyltrimethylene ketal)
• Molecular Formula: C₁₁H₁₈O₃
• Molecular Weight: 198.26
• CAS Registry Number: 69225-59-8
• EC Number: 273-918-4
• SMILES: CC1(COC2(CCC(=O)CC2)OC1)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 45-50 °C (Expl.)
• Index of Refraction: 1.484, Calc.^*
• Boiling Point: 295.4±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 123.3±13.8 °C, Calc.^*, 113 °C (Expl.)

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

Safety Data

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

Hazard Classification

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

Discovery and Applications

3,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-9-one is a unique chemical compound with a spirocyclic structure that has attracted considerable interest in the fields of organic synthesis and materials science. The molecule is characterized by the fusion of a dioxane ring and a cyclohexane ring, forming a highly rigid and stable framework. This structural feature imparts specific reactivity, which makes the compound useful in the synthesis of various organic and polymeric materials. 3,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-9-one is often used as a building block in the preparation of more complex molecules, and its chemical properties have been explored in both synthetic and applied chemistry.

The discovery of 3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-one can be traced back to early research focused on spiro compounds, which are known for their unique chemical and physical properties. The compound was initially synthesized as part of efforts to develop new structures with potential for application in organic materials and pharmaceuticals. The dioxaspiro structure in particular has been shown to offer stability and reactivity that are advantageous in various chemical reactions, including nucleophilic substitution and electrophilic addition.

3,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-9-one finds applications in the synthesis of high-performance materials, particularly in the field of polymer chemistry. Its rigid spirocyclic structure is useful for the development of polymers with specific mechanical properties, such as high strength and flexibility. The compound can be incorporated into copolymers, where it enhances the thermal and chemical stability of the resulting material. These properties are particularly valuable in industries where durability and resistance to degradation are crucial, such as in aerospace, automotive, and electronics applications.

In addition to its role in polymer chemistry, 3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-one has potential applications in drug design and medicinal chemistry. The compound’s unique structure offers opportunities for the development of bioactive molecules, particularly those aimed at targeting specific receptors or enzymes. Its ability to adopt different conformations and interact with biological systems in a specific manner makes it an attractive scaffold for the design of new therapeutic agents. Research in this area is still ongoing, but early studies suggest that spirocyclic compounds like 3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-one may play an important role in future drug discovery efforts.

The compound has also shown promise as a potential intermediate in the synthesis of other complex organic molecules. Its stability and reactivity make it a useful building block for the preparation of a variety of chemical entities, including those used in agrochemicals, specialty chemicals, and fine chemicals. The ability to modify the compound's structure through simple chemical reactions adds to its versatility, making it a valuable tool in both research and industry.

Overall, 3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-one is a compound of considerable interest due to its unique structure and reactivity. It serves as an important building block in the development of advanced materials, drug discovery, and organic synthesis. As research progresses, the applications of this compound are likely to expand, offering new possibilities in both industrial and scientific settings.

References

2009. γ-Carbolines and their hydrogenated derivatives. 1. Aromatic γ-carbolines: methods of synthesis, chemical and biological properties (review). Chemistry of Heterocyclic Compounds, 45(8).
DOI: 10.1007/s10593-009-0373-9

2006. Guanidines in Organic Synthesis. Synthesis, 2006(8).
DOI: 10.1055/s-2006-926325