Also referred to as 2-(2-Chlorophenyl)-2-nitrocyclohexanone, this cyclohexanone derivative is frequently employed as an intermediate in medicinal chemistry and organic synthesis. It is mostly employed in laboratory research and pharmaceutical manufacturing processes for the synthesis of drugs and bioactive molecules.
For instance, 2-(2-Chlorophenyl)-2-nitrocyclohexanone CAS 2079878-75-2 is a crucial step in the production of the medication ketamine. Reactant 2-(2-Chlorophenyl)-cyclohexanone is used in the intramolecular enolate O-arylation of α-arylketones catalyzed by palladium phosphine to produce benzofurans. Cs2CO3 (6.5 g, 20 mmol), Pd2(dba)3 (184 mg, 0.2 mmol), and Xantphos (139 mmol, 0.24 mmol) were added to a flame-dried flask.
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Properties of Structure
Two reaction centers are provided by the nitro group and the carbonyl group of 2-(2-Chlorophenyl)-2-nitrocyclohexanone, which is composed of a nitro group and a highly functionalized cyclohexanone unit. It is highly reactive and capable of undergoing addition, reduction, and substitution reactions, among other chemical reactions. While it is fairly stable at room temperature, it can break down into harmful gases when exposed to extreme heat, strong acids, or strong alkalis.
What Uses Does 2-(2-Chlorophenyl)-2-Nitrocyclohexanone Have?
Here are some applications of 2-(2-Chlorophenyl)-2-nitrocyclohexanone we will discuss here;
● Synthesizing of Norketamine from 2-(2-chlorophenyl)-2-nitrocyclohexanone
Norketamine is a derivative of ketamine a well-known anesthetic and analgesic medication. Ketamine is often used in both human and veterinary medicine. The production of norketamine typically involves the transformation or metabolization of ketamine. It’s important to note that the specifics of the production process may vary depending on the intended use of norketamine, whether for medical, research, or other purposes.
2-(2-chlorophenyl)-2-nitrocyclohexanone plays an important role in the synthesis of norketamine. A new continuous flow process was developed to synthesize this pharmaceutical intermediate. This process involves several steps such as α-bromination, imination/rearrangement, and α-iminol rearrangement. This approach offers high yields and various processing advantages, making it a promising method for large-scale production.
● Method for Preparing Ketamine Intermediates
Ketamine, a derivative of amphetamine-like compounds, is an intravenous general anesthetic used for a variety of medical applications. Existing syntheses of ketamine involve the production of 1-hydroxycyclopentyl-o-chlorophenone. However, a new method was developed using 2-(2-chlorophenyl)-2-nitrocyclohexanone as an intermediate compound. This method has a simpler route, lower cost, and easier operation compared to traditional synthesis methods.
● Synthesis of NMDA Receptor Antagonists by 2-(2-chlorophenyl)-2-nitrocyclohexanone
NMDA-type glutamate receptors (NMDARs) are involved in the transmission of excitatory signals in the central nervous system It is an important receptor for 2-(2-chlorophenyl)-2-nitrocyclohexanone is used in the synthesis of (phenyl)octahydrobenzo ]oxazine/oxadipine, which acts as an NMDA receptor antagonist. These compounds can modulate NMDAR activation and have potential applications in a variety of physiological and biochemical reactions.
Activated zinc powder (6 equivalents) is gradually added to a solution of 2-(2-Chlorophenyl)-2-nitrocyclohexanone (50.7 mg) in acetic acid (2.0 mL) while stirring in an argon environment. For twelve hours, the reaction mixture is swirled at room temperature. In order to eliminate insoluble solids, the reaction mixture is filtered after the reaction. After reducing the pressure and concentrating the filtrate, dichloromethane is used to dilute the residue. To obtain the combined organic layers, the residue is extracted with dichloromethane (3×10 mL) and washed with saturated sodium bicarbonate (5.0 mL).
An intermediate in organic synthesis and medicinal chemistry, especially in the synthesis and modification of drug molecules, is 2-(2-Chlorophenyl)-2-nitrocyclohexanone. One possible application for it would be in the production of the medication ketamine, an analgesic and intravenous anesthetic. It stimulates the reticular system, inhibits the medial thalamic nucleus specifically, and prevents the spinal reticular structure bundle’s ascending conduction. It also exhibits some affinity for central nervous system opioid receptors.