& Fluorinated Bioactive Compounds
Introduction of fluorine into a certain position of bioactive compound such as a pharmaceutical and an agricultural chemical may remarkably reduce the toxicity of the compound, or improve the efficiency of medicine. This is due to the mimic and blocking effect characterized by fluorine. Many compounds, such as 5-fluorouracil, have been reported as success case.
Attempts to efficiently synthesize fluorine-containing compounds are performed in many fields. Methods to introduce fluorine into a certain position through the use of fluorinating agents or the use of fluorine-containing building blocks have been reported.
Recently, triethyl 2-fluoro-2-phosphonoacetate has increasingly been utilized as a useful bifunctional fluorine-containing intermediate. This compound is very useful in the generation of physiologically active compounds because it can generate α-fluoro-α,β-unsaturated ester from the reaction with carbonyl compounds in the presence of a base. A subsequent reduction of the above ester leads to the corresponding aldehyde or alcohol. As examples, vitamin A derivatives1), pheromone of insect origin, synthesis of Pyrethroide having insecticidal efficacy, etc., can be given.
Electrophilic Fluorinating Reagents
Nucleophilic Fluorinating Reagents
Fits Reagents
Fluorinated Building Blocks
Fluorinated Bioactive Compounds
Electrophilic Fluorinating Reagents
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Nucleophilic Fluorinating Reagents
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Fits Reagents
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Fluorinated Building Blocks
Aliphatic Compounds
Heterocyclic Compounds
Fluorinated Bioactive Compounds
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Literature
R. S. H. Liu, H. Matsumoto, A. E. Asato, M. Denny, Y. Shichida, T. Yoshizawa, F. W. Dahlquist, J. Am. Chem. Soc., 1981, 103, 7195 [DOI]; A. J. Lovey, B. A. Pawson, J. Med. Chem., 1982, 25, 71 [DOI].
2) Triethyl 2-Fluoro-2-phosphonoacetate
M. Kikuchi, T. Onozawa, Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem., Jpn), 1997, 55, 88.
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