922500-93-4

Usage

Uses

Used in Chemical Synthesis Industry:
Oxetan-3-ylidene-acetaldehyde is used as a key intermediate in the synthesis of various organic compounds for [application reason]. Its aldehyde properties make it a versatile building block in the production of complex molecules and pharmaceuticals.
Used in Resin and Plastics Production:
Oxetan-3-ylidene-acetaldehyde is used as a monomer or a precursor in the production of resins and plastics for [application reason]. Its reactive aldehyde group can be polymerized or copolymerized with other monomers to create materials with specific properties, such as increased strength, flexibility, or chemical resistance.
Used in Pharmaceutical Industry:
Oxetan-3-ylidene-acetaldehyde is used as a starting material or a building block in the development of pharmaceutical compounds for [application reason]. Its unique structure and reactivity can be exploited to design and synthesize new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
Oxetan-3-ylidene-acetaldehyde is used as a component in the formulation of agrochemicals, such as pesticides and herbicides, for [application reason]. Its chemical properties can be utilized to enhance the effectiveness of these products or to improve their environmental compatibility.

InChI:InChI=1/C5H6O2/c6-2-1-5-3-7-4-5/h1-2H,3-4H2

Upstream product

• 6704-31-0 oxetan-3-one 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 

Downstream Products

• 922501-06-2 [3-(4-tert-butyl-phenyl)-oxetan-3-yl]-acetaldehyde 

Relevant academic research and scientific papers

Synergistic Catalysis for the Asymmetric [3+2] Cycloaddition of Vinyl Aziridines with α,β-Unsaturated Aldehydes

The first asymmetric [3+2] cycloaddition of vinyl aziridines with α,β-unsaturated aldehydes, based on synergistic catalysis, is disclosed. This methodology allows the formation of attractive pyrrolidine structures in good yields (up to 84 %), moderate diastereoselectivity, and high enantioselectivity values (up to >99 % ee). Additionally, a tricyclic pyrrolidine core structure found in biologically active molecules was synthesized in a one-pot fashion by using the presented reaction concept. Finally, a mechanistic proposal is outlined.

Oxetanes in drug discovery: Structural and synthetic insights

An oxetane can trigger profound changes in aqueous solubility, lipophilicity, metabolic stability, and conformational preference when replacing commonly employed functionalities such as gem-dimethyl or carbonyl groups. The magnitude of these changes depends on the structural context. Thus, by substitution of a gem-dimethyl group with an oxetane, aqueous solubility may increase by a factor of 4 to more than 4000 while reducing the rate of metabolic degradation in most cases. The incorporation of an oxetane into an aliphatic chain can cause conformational changes favoring synclinal rather than antiplanar arrangements of the chain. Additionally spirocyclic oxetanes (e.g., 2-oxa-6-aza-spiro[3.3]heptane) bear remarkable analogies to commonly used fragments in drug discovery, such as morpholine, and are even able to supplant the latter in its solubilizing ability. A rich chemistry of oxetan-3-one and derived Michael acceptors provide venues for the preparation of a broad variety of novel oxetanes not previously documented, thus providing the foundation for their broad use in chemistry and drug discovery.

Oxetanes as promising modules in drug discovery

(Chemical Equation Presented) Ring the changes: Introduction of an oxetane ring results in remarkably improved physico- and biochemical properties of the underlying scaffold. The oxetane ring confers enhanced solubility, reduces the metabolic degredation, lipophilicity, and amphiphilicity, and modulates the basicity of a nearby amine group.