1-Isopropylazetidin-3-ol

Historical Context and Significance of Azetidine (B1206935) Scaffolds in Chemical Sciences

Historically, the synthesis of azetidine derivatives presented considerable challenges due to the inherent ring strain of the four-membered system. medwinpublishers.com This made them less explored compared to their five- and six-membered counterparts, pyrrolidines and piperidines. rsc.org However, the discovery of naturally occurring and synthetic azetidine-containing molecules with significant biological activities spurred greater interest in this scaffold. nih.govrsc.org Natural products like azetidine-2-carboxylic acid, a toxic mimic of proline, and the penams, a class of β-lactam antibiotics, highlighted the potential of the azetidine ring in interacting with biological targets. wikipedia.orgjmchemsci.com

The development of more sophisticated synthetic methods has made a wider range of azetidine derivatives accessible. nih.gov This has led to their incorporation into a diverse array of molecules with applications in medicinal chemistry and materials science. rsc.orgresearchgate.net Azetidine scaffolds are now recognized as privileged motifs in drug discovery, appearing in bioactive molecules and approved drugs. rsc.orgresearchgate.net Their unique three-dimensional structures and ability to act as bioisosteres for other cyclic and acyclic fragments have made them valuable tools for chemists.

The Azetidine Ring System: Structural Features and Inherent Strain Energy in Organic Chemistry

The defining characteristic of the azetidine ring is its significant ring strain, estimated to be approximately 25.4 kcal/mol. rsc.org This strain arises from the deviation of bond angles from the ideal tetrahedral angle and eclipsing interactions between adjacent hydrogen atoms. This stored energy makes the ring susceptible to ring-opening reactions under certain conditions, a reactivity that can be harnessed for synthetic transformations. rsc.orgrsc.org

Despite this strain, the azetidine ring is notably more stable than its three-membered analog, aziridine (B145994) (ring strain ~27.7 kcal/mol), making azetidines easier to handle and isolate. rsc.orgresearchgate.net The azetidine ring is not planar and adopts a puckered conformation to alleviate some of the torsional strain. nih.gov The degree of puckering can be influenced by the nature and position of substituents on the ring. researchgate.net The nitrogen atom in the azetidine ring imparts basicity to the molecule, although it is generally a weaker base than other saturated heterocyclic amines due to the s-character of the nitrogen lone pair in the strained ring. ontosight.ai

Overview of 1-Isopropylazetidin-3-ol within the Azetidinol (B8437883) Class

This compound belongs to the azetidinol class of compounds, which are characterized by the presence of a hydroxyl group on the azetidine ring. ontosight.ai Specifically, it is a derivative of 3-azetidinol, where an isopropyl group is attached to the nitrogen atom. ontosight.ai

Table 1: Physicochemical Properties of this compound

This data is compiled from chemical databases. chemnet.com

The presence of both a hydroxyl group and a tertiary amine within the strained four-membered ring gives this compound a unique combination of functional groups and stereochemical properties. The isopropyl group provides steric bulk, which can influence the molecule's conformation and its interactions with other molecules. The hydroxyl group can act as both a hydrogen bond donor and acceptor, contributing to its physical properties and potential biological interactions.

Research Scope and Objectives for this compound Studies

Research into this compound and related azetidinols is driven by several key objectives. A primary focus is its utilization as a building block in organic synthesis. The strained ring system and the presence of functional groups make it a versatile synthon for the construction of more complex molecules, including other heterocyclic systems.

In the context of medicinal chemistry, this compound serves as a scaffold for the design and synthesis of novel compounds with potential therapeutic applications. While specific clinical data for this compound is limited, its structural analogs are investigated for a range of biological activities. The unique three-dimensional arrangement of its functional groups can be exploited to achieve specific interactions with biological targets such as enzymes and receptors. Studies have noted that low yields in certain synthetic routes involving this compound have historically been a challenge. google.com