2-(Dodecyloxy)-6-methyl-4H-benzo[d][1,3]oxazin-4-one
[CAS# 282526-87-8]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 2-(Dodecyloxy)-6-methyl-4H-benzo[d][1,3]oxazin-4-one
• Molecular Formula: C₂₁H₃₁NO₃
• Molecular Weight: 345.48
• CAS Registry Number: 282526-87-8
• SMILES: CCCCCCCCCCCCOC1=NC2=C(C=C(C=C2)C)C(=O)O1

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

2-(Dodecyloxy)-6-methyl-4H-benzo\[d]\[1,3]oxazin-4-one is a synthetic organic compound belonging to the class of 1,3-oxazinones. Its molecular structure consists of a fused aromatic system incorporating a 1,3-oxazin-4-one ring, with a methyl group at the 6-position and a long-chain dodecyloxy (C₁₂H₂₅O–) substituent at the 2-position. This amphiphilic structure, containing both hydrophilic and lipophilic regions, gives the compound distinctive physicochemical properties that have been of interest in materials and surfactant chemistry.

The benzo\[d]\[1,3]oxazin-4-one core is a heterocyclic structure that has been explored for its potential as a scaffold in medicinal and materials chemistry. Substitution with a dodecyloxy chain introduces significant hydrophobicity and can influence aggregation behavior in solution, making the compound relevant for studies involving self-assembly, micelle formation, or interfacial activity. The presence of the long alkyl chain also imparts low water solubility and affinity for lipid environments, which is often exploited in the design of amphiphilic agents.

Although there is no evidence that 2-(dodecyloxy)-6-methyl-4H-benzo\[d]\[1,3]oxazin-4-one is used as a pharmaceutical agent or registered industrial chemical, related oxazinone derivatives have been investigated for their biological activity, including antimicrobial, anticancer, and enzyme inhibitory properties. The oxazinone ring can serve as a pharmacophore in drug discovery efforts due to its potential interactions with biological targets via hydrogen bonding and π-stacking interactions.

In materials science, compounds with long alkyl chains and rigid aromatic cores such as this one are of interest for their ability to form organized molecular assemblies. These can include monolayers, bilayers, vesicles, or liquid crystalline phases, depending on concentration, temperature, and solvent conditions. Such properties are valuable in the formulation of surface-active agents, emulsifiers, or molecular templates for nanostructured materials.

Synthesis of 2-(dodecyloxy)-6-methyl-4H-benzo\[d]\[1,3]oxazin-4-one typically involves the etherification of a phenolic precursor with dodecyl bromide or similar alkyl halide under basic conditions, followed by cyclization to form the oxazinone ring. The methyl group can be introduced through alkylation at the appropriate step, depending on the synthetic route. The overall process requires careful control to ensure regioselectivity and purity, particularly in the final cyclization stage.

Spectroscopic methods such as nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared (IR) spectroscopy are used to confirm the structure and substitution pattern of the synthesized product. The dodecyloxy group gives characteristic aliphatic signals in the NMR spectrum, while the oxazinone ring can be identified by its carbonyl stretch in the IR spectrum and heteroaromatic chemical shifts in NMR.

In summary, 2-(dodecyloxy)-6-methyl-4H-benzo\[d]\[1,3]oxazin-4-one is a synthetic oxazinone derivative with amphiphilic properties, combining a long hydrophobic alkyl chain with a heterocyclic aromatic core. While it is not a marketed compound, its structural features are of interest in research areas involving molecular self-assembly, surfactant development, and heterocyclic compound libraries for chemical and biological studies.