trifluoromethyl

トリフルオロメチル

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/02/27 23:59:24」(JST)

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Trifluoromethyl is a functional group in organofluorines that has the formula -CF₃. The naming of is group is derived from the methyl group (which has the formula -CH₃), by replacing each hydrogen atom by a fluorine atom. The trifluomethyl group has a significant electronegativity that is often described as being intermediate between the electronegativities of fluorine and chlorine. For this reason, trifluoromethyl-substituted compounds are often strong acids, such as trifluoromethanesulfonic acid and trifluoroacetic acid. In other cases, the trifluoromethyl group is employed to lower the basicity of organic compounds or to confer distinctive solvation properties (e.g. trifluoroethanol).

The trifluoromethyl group occurs in certain pharmaceuticals, drugs, and abiotically synthesized natural fluorocarbon based compounds. The medicinal use of the trifloromethyl group dates from 1928, although research became more intense in the mid-1940s. The trifluoromethyl group is often used as a bioisostere to create derivatives by replacing a chloride or a methyl group. This can be used to adjust the steric and electronic properties of a lead compound, or to protect a reactive methyl group from metabolic oxidation. Some notable drugs containing trifluoromethyl groups include efavirenz (Sustiva), an HIV reverse transcriptase inhibitor; fluoxetine (Prozac), an antidepressant; and celecoxib (Celebrex), a non-steroidal anti-inflammatory.

Synthesis

Main article: Trifluoromethylation

Various methods exist to introduce this functionality. Carboxylic acids can be converted to trifluoromethyl groups by treatment with sulfur tetrafluoride and trihalomethyl compounds, particularly trifluoromethyl ethers and trifluoromethyl aromatics, are converted into trifluoromethyl compounds by treatment with antimony trifluoride/antimony pentachloride (the Swarts reaction). Another route to trifluoromethyl aromatics is the reaction of aryl iodides with trifluoromethyl copper. Finally, trifluoromethyl carbinols and ketones can be prepared by reaction of aldehydes and esters with Ruppert's reagent.

References

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English Journal

• Two different spectrophotometric determinations of potential anticancer drug and its toxic metabolite.

• Farid NF1, Abdelwahab NS2.
• Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2015 Jun 15;145:360-7. doi: 10.1016/j.saa.2015.03.009. Epub 2015 Mar 6.
• Flutamide is a hormone therapy used for men with advanced prostate cancer. Flutamide is highly susceptible to hydrolysis with the production of 3-(trifluoromethyl)aniline, which is reported to be one of its toxic metabolites, impurities and related substances according to BP and USP. Flutamide was f
• PMID 25795610

• N-((1,3-Diphenyl-1H-pyrazol-4-yl)methyl)anilines: A novel class of anti-RSV agents.

• Fioravanti R1, Desideri N2, Biava M2, Droghini P2, Atzori EM2, Ibba C3, Collu G3, Sanna G3, Delogu I3, Loddo R4.
• Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2015 Jun 1;25(11):2401-4. doi: 10.1016/j.bmcl.2015.04.006. Epub 2015 Apr 9.
• A series of N-((1,3-diphenyl-1H-pyrazol-4-yl)methyl)anilines were synthesized and evaluated in vitro for cytotoxicity and antiviral activity against a large panel of viruses. Most of the tested compounds interfered with RSV replication in the micromolar concentrations (EC50s ranging from 5μM to 28�
• PMID 25913116

• FTY720 Phosphate Activates Sphingosine-1-Phosphate Receptor 2 and Selectively Couples to Gα12/13/Rho/ROCK to Induce Myofibroblast Contraction.

• Sobel K1, Monnier L1, Menyhart K1, Bolinger M1, Studer R1, Nayler O1, Gatfield J2.
• Molecular pharmacology.Mol Pharmacol.2015 Jun;87(6):916-27. doi: 10.1124/mol.114.097261. Epub 2015 Mar 11.
• FTY720 phosphate (FTY720-P; 2-amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol, monodihydrogen phosphate ester) is a nonselective sphingosine-1-phosphate (S1P) receptor agonist thought to be devoid of activity at the S1P2 receptor subtype. However, we have recently shown that FTY720-P displays signi
• PMID 25762025

Japanese Journal

• Synthesis of Methoxy-Substituted Diazirinyl Phenylalanine – A Novel Photoreactive Aspartame Derivative for Functional Analysis of Sweet Receptors

• Sakurai Munenori,Masuda Katsuyoshi,Wang Lei,Murai Yuta,Sakihama Yasuko,Hashidoko Yasuyuki,Hatanaka Yasumaru,Hashimoto Makoto
• HETEROCYCLES 88(1), 629, 2014
• … Trifluoromethyl- diazirine, which is one of the most reliable photophores, was introduced to a different site on phenylalanine and the new photoreactive phenylalanine was converted to aspartame derivatives. …
• NAID 120005367406

• 4-TRIFLUOROACETYL-2-PHENYLOXAZOL-5-ONE : VERSATILE TEMPLATE FOR SYNTHESES OF TRIFLUOROMETHYL-SUBSTITUTED HETEROCYCLES

• Saijo Ryosuke,Kurihara Ken-ichi,Kawase Masami
• Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 87(12), 2533-2553, 2013-12-01
• NAID 40019893487

• 拡張Pummerer型反応を駆使したヘテロ芳香族化合物の合成

• 依光 英樹
• 有機合成化学協会誌 71(4), 341-354, 2013-04
• NAID 40019673813

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