(+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one
[CAS# 13173-09-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: (+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one
• Synonyms: bicyclo[3.2.0]hept-2-en-6-one
• Molecular Formula: C₇H₈O
• Molecular Weight: 108.14
• CAS Registry Number: 13173-09-6
• EC Number: 629-476-3
• SMILES: C1C=CC2C1C(=O)C2

Properties

• Density: 1.025
• Boiling point: 158-160 °C
• Refractive index: 1.482-1.483
• Flash point: 66.3 °C

Safety Data

• Hazard Symbols: GHS06;GHS08 Danger
• Risk Statements: H302-H315-H318-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

(+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one is a bicyclic organic compound that has garnered interest in organic synthesis and medicinal chemistry due to its unique structural properties. The compound is a key intermediate in the synthesis of complex natural products and has been utilized in a variety of chemical transformations. The discovery of this compound dates back to studies in the mid-20th century when researchers began exploring the synthesis of bicyclic compounds with strained ring systems, which exhibit distinct reactivity due to their geometric constraints.

The synthesis of (+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one typically involves cycloaddition reactions, which are particularly well-suited for constructing the strained bicyclic core of the molecule. One of the most common methods used in the early studies of this compound was based on the Diels-Alder reaction, a powerful tool for the synthesis of cyclic structures. The strained nature of the bicyclo[3.2.0] system makes this compound an important building block in synthetic chemistry, allowing for subsequent functionalization and manipulation in a variety of chemical reactions.

Applications of (+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one include its use as a starting material for the synthesis of bioactive molecules. Its strained ring system and the presence of a reactive ketone group make it a versatile intermediate in the preparation of complex molecules, particularly in the field of pharmaceutical chemistry. The compound’s ability to undergo a range of chemical transformations, such as nucleophilic additions, reductions, and rearrangements, makes it valuable for constructing diverse chemical scaffolds that can serve as potential therapeutic agents.

The importance of this compound in organic synthesis lies in its utility as a platform for building more complex structures. For example, it has been employed in the synthesis of natural products that exhibit biological activity, including terpenes and alkaloids. In addition, the compound's reactivity has been harnessed in the development of new synthetic methodologies, where it acts as a reactive intermediate in multistep transformations.

(+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one remains an important molecule in synthetic chemistry, particularly for researchers focused on the development of novel chemical reactions and the synthesis of bioactive compounds. Its discovery and subsequent applications highlight the significance of strained ring systems in expanding the toolbox of organic chemistry.

References

1989. Chemoenzymatic large-scale preparation of homochiral bicyclo[3.2.0]hept-2-en-6-one. Biotechnology Letters, 11(10).
DOI: 10.1007/bf01044097

2016. Baeyer-Villiger oxidations: biotechnological approach. Applied Microbiology and Biotechnology, 100(15).
DOI: 10.1007/s00253-016-7670-x

2005. Microbial transformations 59: First kilogram scale asymmetric microbial Baeyer-Villiger oxidation with optimized productivity using a resin-based in situ SFPR strategy. Biotechnology and Bioengineering, 92(2).
DOI: 10.1002/bit.20636