22515-18-0 | 4,4-Difluorocyclohexanone

CAS:22515-18-0 | 4,4-Difluorocyclohexanone ,Description

4,4-Difluorocyclohexanone (DFC) is a versatile, fluorinated ketone, which is widely used in organic synthesis and in the production of pharmaceuticals, agrochemicals, and other specialty chemicals. DFC has been used as a starting material for many synthetic transformations and is also used as a reagent in the synthesis of a variety of compounds. It has also been used as a catalyst in the synthesis of polymers and as a solvent for the preparation of polymers. DFC is a relatively new compound and its properties are still being studied.
 

Scientific Research Applications

Organocatalysis and Asymmetric Synthesis

4,4-Difluorocyclohexanone derivatives play a crucial role in organocatalysis and asymmetric synthesis. For instance, they are involved in highly stereoselective and recyclable organocatalysis for asymmetric Michael addition of cyclohexanone to nitroolefins, showcasing high yields and excellent diastereoselectivities (Miao & Wang, 2008). Furthermore, they participate in stereoselective synthesis, such as the synthesis of substituted bicyclo[3.3.1]nonan-9-ones through additions of enamines of cyclohexanones to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one (Andrew et al., 2000).

Synthesis of β-Keto Esters and Building Blocks

4,4-Difluorocyclohexanone derivatives are pivotal in the synthesis of β-keto esters and various building blocks for natural products and medicinal chemistry. An efficient, scalable one-pot methodology utilizes these compounds for the synthesis of 4,4-disubstituted cyclohexane β-keto esters, highlighting their importance in constructing complex molecular architectures (Degraffenreid et al., 2007).

Catalysis and Selective Hydrogenation

These compounds are also integral to catalytic processes and selective hydrogenation. A particular study demonstrates the use of a Pd@carbon nitride catalyst, showing high activity and promoting the selective formation of cyclohexanone under mild conditions, emphasizing the role of 4,4-Difluorocyclohexanone in catalytic efficiency and selectivity (Wang et al., 2011).

Biocatalysis and Baeyer-Villiger Oxidations

In biocatalysis, strains of Escherichia coli overexpressing cyclohexanone monooxygenase have been utilized for Baeyer-Villiger oxidations of 4-mono- and 4,4-disubstituted cyclohexanones. This showcases the versatility of 4,4-Difluorocyclohexanone derivatives in enzymatic reactions and the production of chiral building blocks (Mihovilovic et al., 2001).

Material Science and Polymer Synthesis

Furthermore, these derivatives find applications in material science and polymer synthesis. For instance, they are used in the synthesis of high-performance polyesters from bio-based materials, such as poly(1,4-cyclohexanedimethylene furandicarboxylate) (PCF), synthesized from furandicarboxylic acid (FDCA) and 1,4-cyclohexanedimethanol (CHDM), indicating their potential in developing sustainable, high-performance materials (Wang et al., 2018).

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