(−)-3-(1-Phenylpropyl)-4-hydroxycoumarin

Valente, E.; Trager, William; Lingafelter, E. C.

doi:10.1107/s056774087600277x

Cited by 11 publications

(1 citation statement)

References 4 publications

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“…Other investigators used chemical reactivity [27][28][29][30], ultraviolet spectroscopy [29,[31][32][33][34][35][36], infrared spectroscopy [29,30,34,[37][38][39][40] and proton nuclear magnetic resonance spectroscopy [40] to probe the 4-hydroxycoumarin-2,4-chromadione-2-hydroxychrome equilibrium. X-ray crystallographic studies confirmed in every case studied up through the early 1970s that, at least in the solid state, the 4-hydroxycoumarin form predominates, based on the bond lengths in the pyranone ring [16,17,[41][42][43][44][45][46][47].…”

Section: Determining Tautomeric Equilibriamentioning

confidence: 98%

Warfarin: history, tautomerism and activity

Porter

2010

J Comput Aided Mol Des

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The anticoagulant drug warfarin, normally administered as the racemate, can exist in solution in potentially as many as 40 topologically distinct tautomeric forms. Only 11 of these forms for each enantiomer can be distinguished by selected computational software commonly used to estimate octanol-water partition coefficients and/or ionization constants. The history of studies on warfarin tautomerism is reviewed, along with the implications of tautomerism to its biological properties (activity, protein binding and metabolism) and chemical properties (log P, log D, pK (a)). Experimental approaches to assessing warfarin tautomerism and computational results for different tautomeric forms are presented.

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Section: Determining Tautomeric Equilibriamentioning

confidence: 98%

Warfarin: history, tautomerism and activity

Porter

2010

J Comput Aided Mol Des

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4‐Hydroxycoumarin/2‐hydroxychromone tautomerism: Infrared spectra of 2‐¹³c and 3‐D labeled 4‐hydroxycoumarin and its anion

Obaseki

Porter

Trager

1982

Journal of Heterocyclic Chem

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Bands with primarily v (C=O) and v (C=O) character in the spectra of 4‐hydroxycoumarin and its anion were identified by isotopic substitution with either 13C or deuterium. Two bands of each type were found for spectra of 4‐hydroxycoumarin in solution in chloroform, dioxane, or dimethylsulfoxide, with v (C=O) at 1704–1733 cm−1 and ∼ 1567 cm−1. Two bands, at 1618 and 1559 cm−1, are associated with v (C=C) in the spectrum of crystalline 4‐hydroxycoumarin monohydrate, but only a single v (C=O) band at ∼ 1655 cm−1 was observed. Anhydrous 4‐hydroxycoumarin has v (C=O) bands at ∼ 1700 cm−1 and a shoulder at ∼ 1670 cm−1. The strong band at 1660 cm−1 in the spectrum of 4‐hydroxycommarin anion in dimethylsulfoxide solution is due to a delocalized v (O = C = O) vibration, whereas the band at 1555 cm−1 has partial v (C=C) character and involves C(3) but not C(2), supporting a fully delocalized char structure for the anion. No evidence for the existence of the 2‐hydroxychromone tautomer was found, except in the case of anhydrous 4‐hydroxycoumarin in the solid state.

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4‐Hydroxycoumarin/2‐hydroxychromone tautomerism: Infrared spectra of 3‐substituted‐2‐¹³c‐4‐hydroxycoumarins

Porter¹,

Trager²

1982

Journal of Heterocyclic Chem

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By isotopic replacement of the carbonyl carbon with 13C, the CO stretching frequency was identified as the highest frequency strongly absorbing band in the 1550–1750 cm−1 region of the infrared spectra of several 3‐substituted 4‐hydroxycoumarins and 3‐substituted 4‐alkoxycoumarins. The compounds selected for study were either known to crystallize as the coumarin tautomeric form by x‐ray diffraction studies or were congeners of such compounds. The carbonyl band varied from 1664 cm−1 in inter‐ or intramolecularly hydrogen bonded derivatives to 1718 cm−1.

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(−)-3-(1-Phenylpropyl)-4-hydroxycoumarin

Cited by 11 publications

References 4 publications

Warfarin: history, tautomerism and activity

Warfarin: history, tautomerism and activity

4‐Hydroxycoumarin/2‐hydroxychromone tautomerism: Infrared spectra of 2‐¹³c and 3‐D labeled 4‐hydroxycoumarin and its anion

4‐Hydroxycoumarin/2‐hydroxychromone tautomerism: Infrared spectra of 3‐substituted‐2‐¹³c‐4‐hydroxycoumarins

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(−)-3-(1-Phenylpropyl)-4-hydroxycoumarin

Cited by 11 publications

References 4 publications

Warfarin: history, tautomerism and activity

Warfarin: history, tautomerism and activity

4‐Hydroxycoumarin/2‐hydroxychromone tautomerism: Infrared spectra of 2‐13c and 3‐D labeled 4‐hydroxycoumarin and its anion

4‐Hydroxycoumarin/2‐hydroxychromone tautomerism: Infrared spectra of 3‐substituted‐2‐13c‐4‐hydroxycoumarins

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4‐Hydroxycoumarin/2‐hydroxychromone tautomerism: Infrared spectra of 2‐¹³c and 3‐D labeled 4‐hydroxycoumarin and its anion

4‐Hydroxycoumarin/2‐hydroxychromone tautomerism: Infrared spectra of 3‐substituted‐2‐¹³c‐4‐hydroxycoumarins