79424-03-6Relevant academic research and scientific papers
A high-yield synthesis of 3-carboethoxy-4-trifluoromethylfuran and some Diels-Alder reactions of this furoate with acetylenic dienophiles
Barlow, Michael G.,Suliman, Nadia N. E.,Tipping, Anthony E.
, p. 59 - 70 (1995)
The reaction of furan with ethyl 4,4,4-trifluorobut-2-ynoate (1) (1.2:1 molar ratio) in vacuo at 40 deg C gives the 1:1 adduct oxanorbornadiene (3) (70percent) and the 2:1 adduct (5) as the endo, exo (5a) (16percent) and exo, exo (5b) (10percent) isomers;
Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a MnI(bpy)(CO)3-coordinated azide
Henry, Lucas,Schneider, Christoph,Mützel, Benedict,Simpson, Peter V.,Nagel, Christoph,Fucke, Katharina,Schatzschneider, Ulrich
supporting information, p. 15692 - 15695 (2015/02/19)
The catalyst-free room temperature iClick reaction of an unsymmetrically 2,3-disubstituted oxanorbornadiene (OND) as a "masked" alkyne equivalent with [Mn(N3)(bpy CH3,CH3)(CO)3] leads to isolation of a phenylalanine ester bioconjugate, in which the model amino acid is linked to the metal moiety via a N-2-coordinated triazolate formed in a cycloaddition-retro-Diels-Alder (crDA) reaction sequence, in a novel approach to bioorthogonal coupling reactions based on metal-centered reactivity.
Towards a biocompatible artificial lung: Covalent functionalization of poly(4-methylpent-1-ene) (TPX) with cRGD pentapeptide
Moeller, Lena,Hess, Christian,Palecek, Jiri,Su, Yi,Haverich, Axel,Kirschning, Andreas,Draeger, Gerald
supporting information, p. 270 - 277 (2013/04/10)
Covalent multistep coating of poly(methylpentene), the membrane material in lung ventilators, by using a copper-free "click" approach with a modified cyclic RGD peptide, leads to a highly biocompatible poly(methylpentene) surface. The resulting modified membrane preserves the required excellent gas-flow properties while being densely seeded with lung endothelial cells.
Selective transition state stabilization via hyperconjugative and conjugative assistance: Stereoelectronic concept for copper-free click chemistry
Gold, Brian,Shevchenko, Nikolay E.,Bonus, Natalie,Dudley, Gregory B.,Alabugin, Igor V.
experimental part, p. 75 - 89 (2012/03/10)
Dissection of stereoelectronic effects in the transition states (TSs) for noncatalyzed azide-alkyne cycloadditions suggests two approaches to selective transition state stabilization in this reaction. First, the formation of both 1,4- and 1,5-isomers is facilitated via hyperconjugative assistance to alkyne bending and C???N bond formation provided by antiperiplanar σ-acceptors at the propargylic carbons. In addition, the 1,5-TS can be stabilized via attractive C-H???F interactions. Although the two effects cannot stabilize the same transition state for the cycloaddition to α,α-difluorocyclooctyne (DIFO), they can act in a complementary, rather than competing, fashion in acyclic alkynes where B3LYP calculations predict up to ～1 million-fold rate increase relative to 2-butyne. This analysis of stereoelectronic effects is complemented by the distortion analysis, which provides another clear evidence of selective TS stabilization. Changes in electrostatic potential along the reaction path revealed that azide polarization may create unfavorable electrostatic interactions (i.e., for the 1,5-regioisomer formation from 1-fluoro-2-butyne and methyl azide). This observation suggests that more reactive azides can be designed via manipulation of charge distribution in the azide moiety. Combination of these effects with the other activation strategies should lead to the rational design of robust acyclic and cyclic alkyne reagents for fast and tunable "click chemistry". Further computational and experimental studies confirmed the generality of the above accelerating effects and compared them with the conjugative TS stabilization by π-acceptors.
COMPOUNDS AND METHODS FOR MODULATING FXR
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Page/Page column 45-46, (2008/06/13)
Compounds of formula (I) wherein variables are as defined herein and their pharmaceutical compositions and methods of use are disclosed as useful for treating dyslipidemia and related diseases.
A short and general approach to the synthesis of styryllactones: (+)-Goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone
Chen, Jian,Lin, Guo-Qiang,Wang, Zhi-Min,Liu, Han-Quan
, p. 1265 - 1268 (2007/10/03)
(+)-Goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone, the representatives of styryllactones have been synthesized in a short and general way. The key steps involve the regioselective asymmetric dihydroxylation and the palladium-catalyzed cross-coupling of cyclic allylic carbonate with vinyltributylstannane.
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).
