rac-(1R,5S)-bicyclo[3.2.0]hept-2-en-6-one, cis(CAS: 71155-05-0)

Rac-(1R,5S)-bicyclo[3.2.0]hept-2-en-6-one, cis is a colorless to white crystalline solid with a molecular weight of approximately 134.23 g/mol. It is poorly soluble in water but soluble in organic solvents like ethanol and dichloromethane. This compound is known for its reactive nature, particularly towards nucleophiles and electrophiles, and it exhibits a high reactivity due to its conjugated double bond system.

Rac-(1R,5S)-bicyclo[3.2.0]hept-2-en-6-one, cis is typically synthesized via a Wittig reaction, where an alkyl phosphonate is reacted with a cyclic ketone. The use of a chiral auxiliary can provide enantioselective synthesis. The reaction is carried out under mild conditions, and the yield can be up to 90%. The use of a Lewis acid catalyst, such as aluminum trichloride, is often employed to enhance reactivity and selectivity.

Rac-(1R,5S)-bicyclo[3.2.0]hept-2-en-6-one, cis is used in various industries. It is a key intermediate in the synthesis of pharmaceuticals, particularly in the development of anti-inflammatory and analgesic drugs. It also finds applications in the polymer industry for the production of functional polymers and in the sensor industry for detecting specific chemical species. Additionally, it is used in the semiconductor industry for the preparation of materials with specific electronic properties.

When handling rac-(1R,5S)-bicyclo[3.2.0]hept-2-en-6-one, cis, it is essential to wear appropriate personal protective equipment (PPE), including gloves, goggles, and a lab coat. This compound should be handled in a well-ventilated area or a fume hood due to its reactive nature. Spills should be cleaned up immediately using appropriate absorbents, and the area should be flushed with water. In case of exposure, seek medical attention. Always refer to the safety data sheet (SDS) for detailed safety information and emergency procedures.