1,4-Oxazepan-5-one
[CAS# 10341-26-1]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 1,4-Oxazepan-5-one
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13
• CAS Registry Number: 10341-26-1
• EC Number: 680-908-7
• SMILES: C1COCCNC1=O

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 80 � 82 ºC (Expl.)
• Index of Refraction: 1.435, Calc.^*
• Boiling Point: 311.1±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 142.0±25.9 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary 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
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

1,4-Oxazepan-5-one is a seven-membered heterocyclic lactam containing both oxygen and nitrogen in its ring system. This structural motif is significant in organic and medicinal chemistry due to its presence in various biologically active compounds. The oxazepan core has been studied for its role in synthetic chemistry, particularly in the design of pharmaceutical agents and bioactive molecules.

The study of oxazepan derivatives, including 1,4-oxazepan-5-one, has been driven by their potential applications in medicinal chemistry. Lactam-containing compounds are known for their stability and ability to participate in hydrogen bonding, making them valuable in drug design. The oxazepan framework has been explored for its potential role in modulating biological activity, particularly in the context of enzyme inhibition and receptor interactions.

Applications of 1,4-oxazepan-5-one and its derivatives have been observed in the synthesis of pharmaceutical intermediates. The seven-membered ring system provides conformational rigidity, which can influence the binding properties of drugs targeting specific proteins or enzymes. Researchers have also investigated oxazepan-based scaffolds for their use in peptidomimetics, where they serve as stable analogs of peptide bonds in drug design.

In synthetic chemistry, 1,4-oxazepan-5-one has been utilized as a precursor in the development of novel heterocyclic compounds. The lactam functionality allows for selective modifications, making it a versatile intermediate in organic synthesis. Various methodologies have been explored for constructing the oxazepan ring system, including cyclization reactions and rearrangement strategies.

The role of 1,4-oxazepan-5-one in drug discovery and material science continues to be an area of interest. Its structural characteristics and reactivity make it a valuable component in the design of new molecules with potential therapeutic applications.

References

Esmail Vessally, Akram Hosseinian, Ladan Edjlali, Ahmadreza Bekhradnia, Mehdi D. Esrafili. New route to 1,4-oxazepane and 1,4-diazepane derivatives: synthesis from N-propargylamines. RSC Advances, 2016, 6, 99793.
DOI: 10.1039/C6RA20718A

Xiaobo Bao, Guoli Wang, Xu Dong, Mengxiao Zhu, Lili Yang, Junjie Zhu, Qingyuan Shi, Hongzhen Zhang, Dongyin Chen. I2/CF3CO2Ag-mediated iodolactonization of various allenoic acids to access versatile 6- to 9- membered ring vinylic iodolactones. Organic & Biomolecular Chemistry, 2024, 22, 2443-2450.
DOI: 10.1039/D4OB00061G

Masayuki Sato, Hiroshi Kuroda, Chikara Kaneko, Toshio Furuya. 7-Methyl-2,3,4,5- tetrahydro-1,4-oxazepin-5-one and the dioxepinone analogue: diastereofacial selectivity in catalytic hydrogenation and the explanation. Journal of the Chemical Society, Chemical Communications, 1994, 687-688.
DOI: 10.1039/C39940000687