The pyridine-catalysed acetylation of phenols and alcohols by acetic anhydride

Bonner, T. G.; McNamara, P. M.

doi:10.1039/j29680000795

Cited by 21 publications

(18 citation statements)

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“…Since the absolute configurations at C-4 and C-2′ of herqueinones have been the subject of comprehensive investigations [9,10], the discrepancy in the specific rotations of 1 and herqueinones needed to be justified. Using a pre-established chemical modification technique [11,12,13], 1 was reduced to 1a , which showed a negative specific rotation ([α]D25 (CHCl 3 ) −23); thus, the 2′ S configuration was confirmed. The absolute configuration was further evaluated via the acetylation of 1a to corresponding 9,11,12-triacetyl derivative 1b (Figure 4).…”

Section: Resultsmentioning

confidence: 99%

Phenalenones from a Marine-Derived Fungus Penicillium sp.

et al. 2019

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Six new phenalenone derivatives (1–6), along with five known compounds (7–11) of the herqueinone class, were isolated from a marine-derived fungus Penicillium sp. The absolute configurations of these compounds were assigned based on chemical modifications and their specific rotations. 4-Hydroxysclerodin (6) and an acetone adduct of a triketone (7) exhibited moderate anti-angiogenetic and anti-inflammatory activities, respectively, while ent-peniciherqueinone (1) and isoherqueinone (9) exhibited moderate abilities to induce adipogenesis without cytotoxicity.

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Section: Resultsmentioning

confidence: 99%

Phenalenones from a Marine-Derived Fungus Penicillium sp.

et al. 2019

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“…For this purpose, two methods were employed. Method A consisted to use acetic anhydride in pyridine at 60 °C [ 43 ] and method B used acetyl chloride without solvent at 140 °C ( Figure 2 ) [ 44 ]. Method A used mild conditions that should reduce degradation but the work-up (treatment with acid and basic solutions) induced sample losses.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Alkyl-Glycerolipids Standards for Gas Chromatography Analysis: Application for Chimera and Shark Liver Oils

et al. 2018

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Natural O-alkyl-glycerolipids, also known as alkyl-ether-lipids (AEL), feature a long fatty alkyl chain linked to the glycerol unit by an ether bond. AEL are ubiquitously found in different tissues but, are abundant in shark liver oil, breast milk, red blood cells, blood plasma, and bone marrow. Only a few AEL are commercially available, while many others with saturated or mono-unsaturated alkyl chains of variable length are not available. These compounds are, however, necessary as standards for analytical methods. Here, we investigated different reported procedures and we adapted some of them to prepare a series of 1-O-alkyl-glycerols featuring mainly saturated alkyl chains of various lengths (14:0, 16:0, 17:0, 19:0, 20:0, 22:0) and two monounsaturated chains (16:1, 18:1). All of these standards were fully characterized by NMR and GC-MS. Finally, we used these standards to identify the AEL subtypes in shark and chimera liver oils. The distribution of the identified AEL were: 14:0 (20–24%), 16:0 (42–54%) and 18:1 (6–16%) and, to a lesser extent, (0.2–2%) for each of the following: 16:1, 17:0, 18:0, and 20:0. These standards open the possibilities to identify AEL subtypes in tumours and compare their composition to those of non-tumour tissues.

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“…It has also been shown unambiguously in the early investigations involving the deuterium isotope effect and kinetic studies that intermolecular hydrogen bonding plays an important role in the acetylation of phenols. [24] Accordingly, hydrogen-bonded phenols are better nucleophiles, and the [a] All the reactions were run at RT on 0.2 g (0.97-1.78 mmol) of the phenol by employing 4 equivalents of acetic anhydride in the presence of 0.02 g (10 wt %) CP-6 in 1 mL of CH 2 Cl 2 as solvent.…”

Section: Diverse Topologies Of Cps and Influence Of Counter Anionsmentioning

confidence: 99%

Porous Coordination Polymers of Diverse Topologies Based on a Twisted Tetrapyridylbiaryl: Application as Nucleophilic Catalysts for Acetylation of Phenols

Seth

Venugopalan

Moorthy

2014

Chemistry A European J

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Porous coordination polymers (CPs) with partially uncoordinated pyridyl rings based on rationally designed polypyridyl linkers are appealing from the point of view of their application as nucleophilic catalysts. A D2d -symmetric tetradentate organic linker L, that is, 2,2',6,6'-tetramethoxy-3,3',5,5'-tetrakis(4-pyridyl)biphenyl, was designed and synthesized for metal-assisted self-assembly aimed at porous CPs. Depending on the nature of the metal ion and the counter anion, the ligand L is found to function as a 3- or 4-connecting building block leading to porous CPs of diverse topologies. The reaction of L with Zn(NO3 )2 and Cd(NO3 )2 yields porous 2 D CPs of "fes" topology, in which the tetrapyridyl linker L serves as a 3-connecting unit with its free pyridyl rings well exposed into the pores. The functional utility of these porous CPs containing uncoordinated pyridyl rings is demonstrated by employing them as efficient heterogeneous nucleophilic catalysts for acetylation of a number of phenols with varying electronic properties and reactivities.

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The pyridine-catalysed acetylation of phenols and alcohols by acetic anhydride

Cited by 21 publications

References 0 publications

Phenalenones from a Marine-Derived Fungus Penicillium sp.

Phenalenones from a Marine-Derived Fungus Penicillium sp.

Synthesis of Alkyl-Glycerolipids Standards for Gas Chromatography Analysis: Application for Chimera and Shark Liver Oils

Porous Coordination Polymers of Diverse Topologies Based on a Twisted Tetrapyridylbiaryl: Application as Nucleophilic Catalysts for Acetylation of Phenols

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