2,2-Dimethyltetrahydropyran-4-one
[CAS# 1194-16-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyran compound
• Name: 2,2-Dimethyltetrahydropyran-4-one
• Synonyms: Tetrahydro-2,2-dimethyl-4H-pyran-4-one
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• CAS Registry Number: 1194-16-7
• EC Number: 802-307-2
• SMILES: CC1(CC(=O)CCO1)C

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*
• Boiling point: 178.3±15.0 °C 760 mmHg (Calc.)^*, 203.6 - 209.1 °C (Expl.)
• Flash point: 60.2±13.9 °C (Calc.)^*
• Index of refraction: 1.429 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H315-H318-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Flammable liquids	Flam. Liq.	4	H227
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2,2-Dimethyltetrahydropyran-4-one is a chemical compound that belongs to the class of tetrahydropyran derivatives. It is characterized by a six-membered ring with five carbon atoms and one oxygen atom, forming a cyclic ether structure. The compound contains two methyl groups attached to the 2-position of the tetrahydropyran ring and a ketone functional group at the 4-position.

This compound is of interest due to its potential applications in organic synthesis and as an intermediate in the preparation of various chemicals. The presence of both a methyl group and a ketone functional group on the tetrahydropyran ring provides opportunities for further chemical modifications, such as nucleophilic substitution, addition reactions, or other transformations. Tetrahydropyran derivatives like 2,2-dimethyltetrahydropyran-4-one are important because they serve as building blocks for the synthesis of more complex molecules.

The synthesis of 2,2-dimethyltetrahydropyran-4-one typically involves the formation of the tetrahydropyran ring system, which can be achieved through a variety of synthetic strategies. One common approach to synthesizing such compounds involves the cyclization of an appropriate precursor molecule, often via a reaction involving an alcohol or a halogenated compound, followed by the introduction of the ketone group. In some cases, a catalytic process may be used to facilitate the formation of the six-membered ring and the selective installation of the functional groups.

The compound's structural features make it a versatile intermediate in organic synthesis. For example, the ketone group can be used as a site for nucleophilic attack, which could lead to the formation of various derivatives. Additionally, the methyl groups at the 2-position could influence the compound's reactivity, potentially leading to selective reactions based on steric effects.

In medicinal chemistry, tetrahydropyran derivatives have been studied for their potential to interact with biological targets. The presence of the ketone group and the cyclic structure may enable these compounds to fit into the binding sites of enzymes or receptors, making them candidates for further investigation as bioactive agents. Some tetrahydropyran-based compounds have been shown to exhibit antimicrobial, antiviral, or anticancer activities, which could suggest that 2,2-dimethyltetrahydropyran-4-one or its derivatives might also possess such properties.

Moreover, tetrahydropyran derivatives are often found in the synthesis of natural products and pharmaceutical agents. The ring system is a common feature in several naturally occurring molecules, and modifying this core structure can lead to the development of new compounds with improved activity or selectivity. For example, some tetrahydropyran-based molecules are utilized as intermediates in the synthesis of alkaloids or other complex natural products that have significant medicinal value.

Another application of 2,2-dimethyltetrahydropyran-4-one is in the field of materials science, particularly in the development of polymers or polymer additives. The functional groups present on the molecule can allow it to interact with other monomers or materials, potentially leading to the formation of novel materials with specific properties, such as increased stability, conductivity, or biodegradability.

In conclusion, 2,2-dimethyltetrahydropyran-4-one is an important compound in organic synthesis, serving as a versatile intermediate for the preparation of more complex molecules. Its structural features make it a potential candidate for various applications, including medicinal chemistry, natural product synthesis, and materials science. Further research into its chemical reactivity and biological activity could reveal additional uses for this compound in both industrial and pharmaceutical settings.