1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenylbutane-1,4-dione
[CAS# 1360540-81-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenylbutane-1,4-dione
• Synonyms: Dalosirvat;Wnt pathway activator 1
• Molecular Formula: C₁₈H₁₆O₄
• Molecular Weight: 296.32
• CAS Registry Number: 1360540-81-3
• SMILES: C1COC2=C(O1)C=CC(=C2)C(=O)CCC(=O)C3=CC=CC=C3

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.586, Calc.^*
• Boiling Point: 500.1±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 223.1±30.2 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+351+338-P302+352

Discovory and Applicatios

1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenylbutane-1,4-dione is a synthetic compound known for its applications in medicinal chemistry and as an intermediate in pharmaceutical development. The molecule combines structural features of a dioxin moiety and a diketone functional group, providing it with distinctive physicochemical and biological properties.

The compound's discovery traces back to investigations into molecules containing the dioxin scaffold, which are known to exhibit a range of pharmacological activities. Researchers have been particularly interested in the incorporation of such structures into small molecules to explore their potential as drug candidates. The diketone group in this compound enhances its ability to participate in Michael addition reactions, making it a versatile intermediate in organic synthesis.

In medicinal chemistry, 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenylbutane-1,4-dione has been studied for its potential antioxidant and anti-inflammatory properties. Compounds featuring the dioxin structure often exhibit the ability to scavenge free radicals and modulate oxidative stress pathways. These properties are of interest for developing therapies for conditions associated with inflammation and oxidative damage, such as neurodegenerative diseases and certain types of cancer.

The compound also plays a role as a precursor in the synthesis of bioactive heterocycles. Its diketone structure allows it to undergo cyclization reactions, enabling the formation of complex molecular frameworks with enhanced biological activity. This makes it valuable in the design of libraries for drug screening programs.

Beyond medicinal applications, 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenylbutane-1,4-dione has found utility in materials science. Researchers have explored its potential as a building block for synthesizing polymers and materials with specialized optical or electronic properties. The dioxin unit, in particular, imparts rigidity and stability, which can enhance the performance of materials in specific applications.

Despite its versatility, the compound's use remains primarily in research contexts. Limited data on its pharmacokinetics and toxicity in humans suggest the need for further studies before its transition into clinical or industrial applications. Advances in synthetic methodologies and high-throughput screening may further expand the potential uses of this compound in diverse scientific fields.