55579-73-2 | 5-(2-TRIFLUOROMETHYL-PHENYL)-CYCLOHEXANE-1,3-DIONE

CAS:55579-73-2 | 5-(2-TRIFLUOROMETHYL-PHENYL)-CYCLOHEXANE-1,3-DIONE,Description

The compound 5-(2-(Trifluoromethyl)phenyl)cyclohexane-1,3-dione is a trifluoromethylated cyclohexane dione, which is a class of compounds known for their potential as building blocks in organic synthesis. These compounds are highly functionalized and can serve as intermediates for the synthesis of various organic and heterocyclic compounds containing a trifluoromethyl group.

Synthesis Analysis

The synthesis of 5-(trifluoromethyl)cyclohexane-1,3-dione has been achieved through a simple process starting from the sodium salt of methyl or ethyl-4-hydroxy-2-oxo-6-(trifluoromethyl)cyclohex-3-en-1-oate. This demonstrates the accessibility of such trifluoromethyl building blocks for further chemical synthesis. Another related compound, 5-(trifluoromethyl)cyclohexane-1,2,3-trione, was synthesized in one step by reacting 5-(trifluoromethyl)cyclohexane-1,3-dione with cerium(IV)ammonium nitrate (CAN) in methanol.

Molecular Structure Analysis

The molecular structure of related trifluoromethyl compounds has been studied using NMR and DFT calculations. For instance, the structures of 2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione (NTBC) and its metabolites were thoroughly investigated, revealing insights into their constitution, tautomerism, and stereochemistry. Additionally, the stability of tautomers of similar compounds has been evaluated using Gibbs free energies based on DFT calculations.

Chemical Reactions Analysis

Trifluoromethylated cyclohexane diones are reactive intermediates that can undergo various chemical reactions. For example, triketones of the 2-(3-oxopropyl)cyclohexane-1,3-dione series can react with boron trifluoride etherate to yield novel heterocyclic compounds. Moreover, cyclohexane-1,3-dione derivatives have been shown to behave abnormally in Michael additions to nitro-olefins, leading to the formation of unique butenolide derivatives.

Physical and Chemical Properties Analysis

The physical and chemical properties of 5-(2-(Trifluoromethyl)phenyl)cyclohexane-1,3-dione and related compounds are influenced by the trifluoromethyl group, which is known for its electron-withdrawing character. This group can affect the reactivity and stability of the compounds, as well as their potential for further functionalization. The presence of the trifluoromethyl group also contributes to the unique properties of these compounds, such as their susceptibility to solvolysis under basic conditions.

Scientific Research Applications

Application 1: DNA Targeting Agents

• Summary of the Application : This compound has been used in the synthesis of DNA targeting agents, specifically 1-trifluoroacetyl-3-aryl-5-(2-oxo-2-arylethylthio)-1,2,4-triazoles.
• Methods of Application : The compound was used in a one-pot cascade reaction with 3-mercapto [1,2,4]triazoles in the presence of NBS. This protocol offered a unique approach for functionalizing both N-acylation and S-alkylation in a concerted fashion.
• Results or Outcomes : The synthesized analogs were primarily screened for their ability to bind with the DNA duplex d (CGCGAATTCGCG) 2 using molecular modeling tools. The most promising compound demonstrated a strong binding affinity (Kb = 1 × 10^5 M^−1) with double-helical DNA, particularly within the minor groove.

Application 2: Antimicrobial Activity

• Summary of the Application : The compound has been synthesized and tested for its antimicrobial activity.
• Methods of Application : The compound was synthesized and its antimicrobial activity was investigated in vitro. Docking studies with the active site of the enzymes have been carried out.
• Results or Outcomes : The compound showed moderate action against Candida albicans. It revealed higher activity against Aspergillus niger as well as bacteria such as Escherichia coli and Bacillus cereus. In case of Bacillus cereus, the determined Minimum Inhibitory Concentration (MIC) value is lower than that of AN2690 (Tavaborole).

Application 3: Synthesis of Bioactive Natural Products and Conducting Polymers

• Summary of the Application : This compound is used in the synthesis of m-aryloxy phenols, which are important building blocks for the synthesis of bioactive natural products and conducting polymers.
• Methods of Application : The compound is used in the synthesis of complex m-aryloxy phenols with functional groups, such as esters, nitriles, and halogens. The use of hydrogen bromide and boron tribromide (BBr 3) as catalysts in demethylation reactions represents a valuable approach for the synthesis of m-aryloxy phenols.
• Results or Outcomes : The synthesized m-aryloxy phenols have a wide range of applications, including as antioxidants, ultraviolet absorbers, and flame retardants. They are commonly used in the production of plastics, adhesives, and coatings due to their ability to improve these materials’ thermal stability and flame resistance.

Application 4: Preparation of Antiglaucoma Agent

• Summary of the Application : 3-(Trifluoromethyl)phenol, which can be derived from “5-(2-(Trifluoromethyl)phenyl)cyclohexane-1,3-dione”, was used in the preparation of travoprost, an antiglaucoma agent.
• Methods of Application : The specific methods of application are not detailed in the source.
• Results or Outcomes : The outcome of this application is the production of travoprost, a medication used in the treatment of glaucoma.

Application 5: Synthesis of Bioactive Natural Products and Conducting Polymers

• Summary of the Application : This compound is used in the synthesis of m-aryloxy phenols, which are important building blocks for the synthesis of bioactive natural products and conducting polymers.
• Methods of Application : The compound is used in the synthesis of complex m-aryloxy phenols with functional groups, such as esters, nitriles, and halogens. The use of hydrogen bromide and boron tribromide (BBr 3) as catalysts in demethylation reactions represents a valuable approach for the synthesis of m-aryloxy phenols.
• Results or Outcomes : The synthesized m-aryloxy phenols have a wide range of applications, including as antioxidants, ultraviolet absorbers, and flame retardants. They are commonly used in the production of plastics, adhesives, and coatings due to their ability to improve these materials’ thermal stability and flame resistance.

Application 6: Preparation of Antiglaucoma Agent

• Summary of the Application : 3-(Trifluoromethyl)phenol, which can be derived from “5-(2-(Trifluoromethyl)phenyl)cyclohexane-1,3-dione”, was used in the preparation of travoprost, an antiglaucoma agent.
• Methods of Application : The specific methods of application are not detailed in the source.
• Results or Outcomes : The outcome of this application is the production of travoprost, a medication used in the treatment of glaucoma.

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