6-(4-Fluorophenyl)-2-hydroxypyridine - CAS 1111111-04-6
Catalog number: 1111111-04-6
Category: Main Product
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1.Rhodium-catalyzed asymmetric 1,4-addition of organoboron reagents to 5,6-dihydro-2(1H)-pyridinones. Asymmetric synthesis of 4-aryl-2-piperidinones.
Senda T1, Ogasawara M, Hayashi T. J Org Chem. 2001 Oct 19;66(21):6852-6.
Catalytic asymmetric synthesis of 4-aryl-2-piperidinones was realized for the first time by asymmetric 1,4-addition of arylboron reagents to 5,6-dihydro-2(1H)-pyridinones in the presence of a chiral bisphosphine-rhodium catalyst. In the reaction introducing 4-fluorophenyl group, the use of 4-fluorophenylboroxine and 1 equiv (to boron) of water at 40 degrees C gave the highest yield of the arylation product with high enantioselectivity (98% ee). The (R)-4-(4-fluorophenyl)-2-piperidinone obtained here is a key intermediate for the synthesis of (-)-Paroxetine.
2.Transition metal ions or acid-induced suppression of photoinduced proton transfer and electron transfer reaction in 5-(4-fluorophenyl)-2-hydroxypyridine: a molecule of dual mode fluorosensitivity.
Samanta A1, Paul BK, Jana S, Guchhait N. Photochem Photobiol. 2010 Sep-Oct;86(5):1022-9. doi: 10.1111/j.1751-1097.2010.00785.x. Epub 2010 Jul 28.
The photophysical properties of 5-(4-fluorophenyl)-2-hydroxypyridine (FP2HP) at different pH and its fluorescence response toward different transition metal ions have been studied by steady-state absorption and emission spectroscopy in combination with quantum chemical calculations. Although keto-enol tautomerization is observed in the excited state, the molecule is weakly fluorescent due to the presence of electron-rich nitrogen atom and relatively electron-deficient fluorine atom, which may lead to photoinduced electron transfer process. In the presence of the transition metal ions, such as Zn(2+) , Cd(2+) , Hg(2+) , etc., the studied molecule exhibits changes in its absorption and emission properties. The present system shows fluorescence enhancement instead of usual quenching in presence of the transition metal ions, such as Fe(2+) and Cu(2+) . Spectral observation leads to the interpretation that this structurally simple molecule can be effectively utilized as a chelation-enhanced fluorescence-based chemosensor for the detection of transition metal ions.
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CAS 1111111-04-6 6-(4-Fluorophenyl)-2-hydroxypyridine

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