3-Hydroxy-1-(4-methoxybenzyl)piperidine-2,6-dione
[CAS# 2357109-89-6]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: 3-Hydroxy-1-(4-methoxybenzyl)piperidine-2,6-dione
• Molecular Formula: C₁₃H₁₅NO₄
• Molecular Weight: 249.26
• CAS Registry Number: 2357109-89-6
• SMILES: COC1=CC=C(C=C1)CN2C(=O)CCC(C2=O)O

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 498.1±45.0 ºC 760 mmHg (Calc.)^*
• Flash point: 255.1±28.7 ºC (Calc.)^*
• Index of refraction: 1.593 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

3-Hydroxy-1-(4-methoxybenzyl)piperidine-2,6-dione is a chemical compound belonging to the class of piperidine derivatives, characterized by its piperidine ring fused with a diketone structure at the 2 and 6 positions. The molecule also features a hydroxyl group at the 3-position and a methoxybenzyl group at the 1-position, which impart specific chemical properties to the compound. This structure makes the compound an interesting target for various synthetic and medicinal chemistry applications.

The synthesis of 3-hydroxy-1-(4-methoxybenzyl)piperidine-2,6-dione typically involves the functionalization of a piperidine intermediate, with selective substitution at the 3-position with a hydroxyl group and at the 1-position with a 4-methoxybenzyl group. The diketone portion of the molecule is typically introduced via cyclization reactions, which create the two carbonyl functionalities at the 2 and 6 positions of the piperidine ring. The methoxy group on the benzyl ring enhances the compound’s electron-donating properties, affecting its reactivity and biological interactions.

In terms of applications, 3-hydroxy-1-(4-methoxybenzyl)piperidine-2,6-dione has attracted attention in medicinal chemistry due to its potential as a bioactive molecule. The hydroxyl group at the 3-position is a reactive site that may facilitate interactions with biological targets, such as enzymes or receptors, while the 4-methoxybenzyl group at the 1-position can help improve the compound’s binding affinity for specific biomolecules. As such, the compound can be considered a valuable lead structure for the development of new therapeutic agents.

One potential application of 3-hydroxy-1-(4-methoxybenzyl)piperidine-2,6-dione is in the field of neurochemistry. The piperidine scaffold is commonly found in compounds with central nervous system (CNS) activity, and the functional groups on this compound suggest it may exhibit neuropharmacological properties. Studies have indicated that piperidine-based compounds can interact with neurotransmitter systems, such as those involving dopamine or serotonin receptors, which could make this molecule useful for the development of treatments for neurological disorders, such as depression or Parkinson’s disease.

In addition, the diketone structure within the piperidine ring may confer reactivity that allows this compound to undergo various chemical transformations. These transformations could enable the synthesis of analogs with modified properties, expanding its utility as a research tool in drug development. The presence of the methoxy group on the aromatic ring also suggests that the compound may exhibit some degree of antioxidant activity, which has been observed for other methoxybenzyl derivatives. This antioxidant property could have potential applications in protecting cells from oxidative stress, which plays a role in a variety of diseases, including neurodegenerative disorders.

Beyond medicinal chemistry, 3-hydroxy-1-(4-methoxybenzyl)piperidine-2,6-dione may also have applications in materials science. The compound's structure, which incorporates both functionalized organic moieties and a heterocyclic ring, may make it suitable for incorporation into polymeric materials or other organic materials with specific electronic or optical properties. These applications are particularly promising in the development of organic electronics or light-emitting devices, where the functionalization of aromatic groups and the inclusion of heterocyclic rings can significantly alter the material’s properties.

The compound’s physical properties, including its solubility in various organic solvents, further enhance its appeal for synthetic and practical applications. The hydroxyl and methoxy groups introduce polarity to the molecule, allowing it to interact with a variety of solvents and biological systems.

In summary, 3-hydroxy-1-(4-methoxybenzyl)piperidine-2,6-dione is a compound of interest in both medicinal and materials chemistry. Its piperidine-based structure, functionalized with hydroxyl and methoxy groups, positions it as a valuable lead compound in the development of bioactive molecules. Its potential neuropharmacological properties, coupled with the reactivity of the diketone group, make it an intriguing candidate for drug development, particularly for neurological conditions. Additionally, its applications in materials science highlight its versatility as a multifunctional compound in various chemical and technological domains.