2840-44-0 | 7-FLUORO-1-TETRALONE

CAS:2840-44-0 | 7-FLUORO-1-TETRALONE,Description

7-Fluoro-1-tetralone is a fluorinated organic compound that is part of the tetralone family, which are ketones derived from tetralin (1,2,3,4-tetrahydronaphthalene). The presence of the fluorine atom at the 7th position of the tetralone ring system can significantly alter the chemical and physical properties of the molecule, potentially leading to unique reactivity and applications in organic synthesis.

Synthesis Analysis

The synthesis of fluorinated tetralone derivatives has been explored in various studies. For instance, the use of fluorotetraphenylbismuth has been reported as an efficient reagent for the alpha-phenylation of carbonyl compounds, which could be applied to the synthesis of fluorinated tetralones. This method demonstrates the potential for high yields and regioselectivity, which is crucial for the synthesis of compounds like 7-Fluoro-1-tetralone. Additionally, the synthesis of various fluorinated indanone, tetralone, and naphthone derivatives has been achieved through Claisen condensations and selective fluorinations, indicating that similar methodologies could be adapted for the synthesis of 7-Fluoro-1-tetralone.

Molecular Structure Analysis

The molecular structure of fluorinated tetralones is influenced by the presence of the fluorine atom. For example, the crystallographic analysis of fluorinated compounds has shown that the introduction of fluorine can lead to unique structural features, such as the preference for a chelated cis-enol form in trifluoroacetylated ketones. This suggests that the molecular structure of 7-Fluoro-1-tetralone could also exhibit distinct characteristics due to the fluorine substitution.

Chemical Reactions Analysis

Fluorinated tetralones can undergo various chemical reactions, leveraging the reactivity of the fluorine atom. The enantioselective electrophilic fluorination of α-aryl-tetralones using N-fluoroammonium salts of cinchonine has been described, which allows for the synthesis of 2-fluoro-2-aryl-1-tetralones with high yields and good enantioselectivity. This reaction showcases the potential for synthesizing enantiomerically enriched fluorinated tetralones, which could be relevant for the synthesis and study of 7-Fluoro-1-tetralone.

Physical and Chemical Properties Analysis

The physical and chemical properties of fluorinated tetralones are expected to be influenced by the fluorine atom's electronegativity and its impact on the electronic structure of the molecule. While specific data on 7-Fluoro-1-tetralone is not provided, the studies on related compounds suggest that fluorination can affect the compound's boiling point, solubility, and stability. The thermal stability of fluorotetraphenylbismuth, for example, indicates that fluorinated tetralones could also exhibit enhanced stability. Additionally, the unique structural features observed in crystallographic studies of fluorinated ketones imply that 7-Fluoro-1-tetralone may have distinct solid-state properties.

Scientific Research Applications

• Summary of the Application: 7-methoxy-1-tetralone is an essential intermediate for the opioid analgesic drug (-)-dezocine. Dezocine plays a vital role in the growing market for analgesics to treat moderate to severe pain resulted from massive surgeries or cancer.
• Methods of Application or Experimental Procedures: The synthesis of 7-methoxy-1-tetralone involves a multi-step continuous-flow strategy. Anisole is mixed with succinic anhydride and AlCl3 in an organic solvent to form 4-(4-methoxyphenyl)-4-oxobutanoic acid through Friedel–Crafts acylation. The corresponding compound is then reduced to 4-(4-methoxyphenyl)butanoic acid, which is treated with MeSO3H to form 7-methoxy-1-tetralone.
• Results or Outcomes: The flow protocol provided the desired product in an overall yield of up to 76.6% with 99% purity, much higher than those from batch process (i.e., 50% yield, 92% purity). Moreover, reaction efficiency is highly improved with a throughput of 0.49 g/h, and the total reaction time is markedly reduced from hours in batch to minutes in flow process.

Safety And Hazards

7-Fluoro-1-tetralone is harmful if swallowed and harmful to aquatic life with long-lasting effects. It should be handled with care, avoiding release to the environment.

Future Directions

While specific future directions for 7-Fluoro-1-tetralone were not found in the available literature, research into fluorinated indanone, tetralone, and naphthone derivatives continues to be of interest due to their potential medicinal, industrial, and herbicidal properties.

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