(1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene(CAS: 19888-34-7)

(1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene is a cyclic compound with a molecular weight of approximately 228.37 g/mol. It is a colorless liquid with a high boiling point at 312°C and a low melting point of -44°C. The compound is moderately soluble in common organic solvents like ethanol and acetone but is insoluble in water. Reactivity studies show it is a stable compound under normal conditions but can undergo ring-opening reactions under acidic conditions. It is also known to be a substrate for certain enzymes and can participate in addition reactions with electrophiles.

(1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene can be synthesized via a stereoselective ring expansion of a cyclic alkyne. Common methods include using palladium catalysts in the presence of tributyltin hydride and sodium bis(trimethylsilyl)amide (NTMS2). The reaction typically yields a high enantiomeric excess, making it suitable for chiral applications. Other methods involve Wittig olefination followed by ring closure, which allows for good control over the stereochemistry and yields.

(1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene finds applications in the pharmaceutical industry as a precursor for the synthesis of chiral compounds and as a ligand in asymmetric catalysis. It is also used in the polymer industry for the synthesis of functionalized polymers with unique properties. Additionally, its use in the semiconductor industry for the fabrication of organic semiconductors and in the sensor industry for the development of biosensors is growing due to its reactivity and stability.

When handling (1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene, it is crucial to wear appropriate personal protective equipment (PPE) such as gloves, safety goggles, and a lab coat. Work should be conducted in a fume hood to minimize exposure. This compound should be stored in a cool, dry place away from oxidizers and acidic substances. In case of a spill, neutralize the area with a base and dispose of the waste according to local regulations. Always consult the Material Safety Data Sheet (MSDS) for detailed safety information and emergency procedures.