76481-01-1Relevant articles and documents
A novel fluorine-metal exchange reaction of pentafluorocrotonate with organocuprate. Generation of β-metallated tetrafluorocrotonate and its cross-coupling reaction
Yamada, Shigeyuki,Takahashi, Toshio,Konno, Tsutomu,Ishihara, Takashi
, p. 3679 - 3681 (2007)
Fluorine-metal exchange reaction of 2,3,4,4,4-pentafluorocrotonates with organocuprate derived from Grignard reagent and CuCN takes place efficiently to generate the β-metallated tetrafluorocrotonate intermediate, which reacts with various electrophiles to give β-substituted 2,4,4,4- tetrafluorocrotonates. The Royal Society of Chemistry.
Fluorine-copper exchange reaction of α,β,γ,γ, γ-pentafluorocrotonates with organocuprates: Generation and cross-coupling reactions of β-metallated α,γ,γ,γ- tetrafluorocrotonates
Yamada, Shigeyuki,Takahashi, Toshio,Konno, Tsutomu,Ishihara, Takashi
, p. 95 - 103 (2013/06/05)
Reaction of α,β,γ,γ,γ-pentafluorocrotonates with organocuprates derived from organomagnesium or zinc reagents in THF at -78 °C for 1 h took place smoothly to generate β-metallated intermediate, of which hydrolysis gave the β-reduction product in good yield. The fluorinated vinylcopper intermediate formed by fluorine-copper exchange was found to be stable at low temperature due to the strong electron-withdrawing effect of a CF3 group, and was readily converted to various types of β-substituted products in good yields with high stereoselectivity by treating with electrophiles, such as iodine and allylic bromides.
Functionalized heterocycles as modulators of chemokine receptor function and methods of use therefor
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, (2008/06/13)
Disclosed are novel compounds having the formula or a physiologically acceptable salt, amide, ester or prodrug thereof. The compounds can be used to modulate (antagonize, agonize) chemokine receptor function. Also disclosed is a method for treating a patient having an inflammatory disease and/or viral infection comprising administering an effective amount of a compound of Formula I. In particular embodiments, the invention is a method for treating a patient infected with HIV.
FLUORINATED ACETYLENES. PART 7. PREPARATION AND SOME REACTIONS OF 4,4,4-TRIFLUOROBUT-2-YNOIC ACID AND 1-PHENYL-4,4,4-TRIFLUOROBUT-2-YN-1-OL
Tajammal, Sabiha,Tipping, Anthony E.
, p. 45 - 57 (2007/10/02)
Treatment of the salt CF3C CLi with alkyl chloroformates affords the compounds CF3C CCO2R (R=Et and CH2Ph) in relatively low yield and with gaseous carbon dioxide yields the acid CF3C CCO2H.Reaction of the acid with diazomethane gives the methyl ester which, with an excess of the reagent, undergoes regiospecific 1,3-dipolar cycloaddition to produce 3-carbomethoxy-4-trifluoromethylpyrazole and hence the 3- and 5-carbomethoxy-1-methyl-4-trifluoromethylpyrazoles.Oxidation of the alcohol CF3C CCH(OH)Ph (active MnO2) affords a 70:23 mixture of 3-benzoyl-2,4-bis(trifluoromethyl)-2-hydroxy-6-phenyl-α-pyran and E-1,3-dibenzoyl-2-trifluoromethylpropene (via the ketone CF3C CCOPh).
Synthesis of Fluorinated Analogues of Geraniol
Poulter, C. Dale,Wiggins, Paul L.,Plummer, Thomas L.
, p. 1532 - 1538 (2007/10/02)
Syntheses of 3-(fluoromethyl)geraniol (4), 3-(difluoromethyl)geraniol (14), and 3-(trifluoromethyl)geraniol (20) are described.The key reaction in the routes to alcohols 4 and 20 which establishes the geranyl Z stereochemistry at the C(2)-C(3) double bond is the cis addition of (4-methylpent-3-en-1-yl)copper reagents to derivatives of ethyl 2-butynoate bearing appropriate functional groups at C(4).Attempts to prepare difluoromethyl alcohol 14 by similar routes were unsuccessful.However, the carbon skeleton of 14 was constructed by a Wittig condensation of 1,1-difluoro-6-methylhept-5-en-2-one (12) with triethyl phosphonoacetate in a reaction that yielded a 72:28 ratio of geranyl/neryl isomers.
