Methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate
[CAS# 123405-97-0]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.24
• CAS Registry Number: 123405-97-0
• SMILES: COC(=O)C1CC2CCCC(C1)C2=O

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.491, Calc.^*
• Boiling Point: 289.9±33.0 ºC (760 mmHg), Calc.^*
• Flash Point: 124.8±25.4 ºC, Calc.^*

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

Discovory and Applicatios

Methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate is a bicyclic organic compound widely used in chemical synthesis and materials science. This molecule is characterized by a bicyclo[3.3.1]nonane ring system, with a carbonyl group at the ninth carbon position and an ester group at the third position, specifically as a methyl carboxylate. Its structure provides rigidity and a unique three-dimensional framework, making it useful in a variety of chemical applications, particularly in synthesizing complex organic compounds and developing new materials.

The discovery and development of compounds like methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate have their roots in the study of bicyclic structures, which are prized for their stability and unique spatial arrangement. In the 20th century, researchers recognized that these bicyclic frameworks could serve as excellent scaffolds for developing molecules with specific biological activities, owing to their rigid structure and predictable geometry. The esterification of such frameworks with methyl groups further expanded their synthetic utility, as it enabled the introduction of functional groups that could be modified or further elaborated in various synthetic pathways.

Methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate has become an important intermediate in the synthesis of biologically active compounds and pharmaceutical agents. Its bicyclic structure is advantageous in medicinal chemistry because it can mimic certain natural products or fit well within biological receptors. The rigidity of the compound also helps maintain the desired orientation of functional groups, which is critical in designing drugs that must interact with specific enzymes or receptors in the body. This has led to its use in synthesizing derivatives for potential anti-inflammatory, analgesic, and antiviral applications.

In addition to its pharmaceutical potential, methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate has found use in materials science, particularly in designing polymers and advanced materials with desirable mechanical properties. The stability of its bicyclic structure, combined with the reactivity of the ester group, allows it to be incorporated into polymer networks, imparting rigidity and thermal stability. This compound’s versatility enables it to serve as a building block for developing resins, coatings, and adhesives that require enhanced durability.

Further research into methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate continues to explore its potential in asymmetric synthesis, where it can act as a chiral scaffold for producing enantiomerically pure compounds. Its bicyclic structure can impose chirality on substituted groups, making it valuable in the synthesis of stereoselective drugs and fine chemicals. The development of novel derivatives and analogs of this compound also expands its application scope, as researchers experiment with substituents at various positions on the bicyclic ring to fine-tune its chemical and physical properties.