5896-50-4

Usage

Preparation

Preparation by Fries rearrangement of 3-ethylphenyl acetate, ? with aluminium chloride, without solvent between 120° and 165° (80–88%), in nitrobenzene at 25° (84–89%) or at 60° (65%), in toluene or in xylene at 100° (56–57%); ? with titanium tetrachloride, without solvent at 120° (88%) or in nitrobenzene at 25° (66%) ; ? with stannic chloride, without solvent at 120° (84%) or in nitrobenzene at 25° (86%); ? with zinc chloride, without solvent at 120° (56%) or in nitrobenzene at 25° (58%).

Upstream product

• 27044-40-2 6-ethyl-2,3-dimethyl-benzofuran 
• 620-17-7 3-ethylphenol 
• 64-19-7 acetic acid 
• 31199-03-8 1,1-dimethoxypentan-3-one 
• 63446-76-4 1-methyl-1,3-bis(trimethylsilyloxy)buta-1,3-diene 
• 7446-70-0 aluminium trichloride 
• 3056-60-8 3-acetoxy-1-ethylbenzene 
• 98-95-3 nitrobenzene 

Downstream Products

• 876-20-0 2,5-diethyl phenol 
• 649551-68-8 7-ethyl-3-hydroxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 
• 91970-44-4 1-<4-Aethyl-2-hydroxy-5-methoxy-phenyl>-aethan-1-on 
• 6068-60-6 3-(2,5-Diethyl-phenoxy)-butan-2-on 
• 108368-11-2 4-acetylamino-N-[4-(4-ethyl-2-hydroxy-phenyl)-thiazol-2-yl]-benzenesulfonamide 
• 108014-49-9 4-amino-N-[4-(4-ethyl-2-hydroxy-phenyl)-thiazol-2-yl]-benzenesulfonamide 

Relevant academic research and scientific papers

Synthesis of functionalized salicylates by formal [3+3] cyclocondensation of 1,3-bis(silyloxy)buta-1,3-dienes with 3-alkoxy-2-en-1-ones

The formal [3+3] cyclization of 1,3-bis(silyloxy)buta-1,3-dienes with 1-aryl-3-ethoxyprop-2-en-1-ones, available by Heck reaction of benzoyl chlorides with ethyl vinyl ether, afforded a variety of 6-arylsalicylates. The reaction of the products with conce

Direct acylation of phenol and naphthol derivatives in a mixture of graphite and methanesulfonic acid

Graphite in methanesulfonic acid is used to prepare o-hydroxyketones by direct acylation of phenol and naphthol derivatives with carboxylic acids. Georg Thieme Verlag Stuttgart.

Optimization of chromone-2-carboxamide melanin concentrating hormone receptor 1 antagonists: Assessment of potency, efficacy, and cardiovascular safety

Evaluation of multiple structurally distinct series of melanin concentrating hormone receptor 1 antagonists in an anesthetized rat cardiovascualar assay led to the identification of a chromone-2-carboxamide series as having excellent safety against the chosen cardiovascular endpoints at high drug concentrations in the plasma and brain. Optimization of this series led to considerable improvements in affinity, functional potency, and pharmacokinetic profile. This led to the identification of a 7-fluorochromone-2-carboxamide (22) that was orally efficacious in a diet-induced obese mouse model, retained a favorable cardiovascular profile in rat, and demonstrated dramatic improvement in effects on mean arterial pressure in our dog cardiovascular model compared to other series reported by our group. However, this analogue also led to prolongation of the QT interval in the dog that was linked to affinity for hERG channel and unexpectedly potent functional blockade of this ion channel.

Potential therapeutic antioxidants that combine the radical scavenging ability of myricetin and the lipophilic chain of vitamin E to effectively inhibit microsomal lipid peroxidation

The flavonol myricetin, reacts with oxygen-centred galvinoxyl radicals 28 times faster than d-α-tocopherol (vitamin E), the main lipid-soluble antioxidant in biological membranes. Moreover, each myricetin molecule reduces twice as many such radicals as vitamin E. However, myricetin fails to protect vitamin E-deficient microsomes from lipid peroxidation as assessed by the formation of thiobarbituric acid reactive substances (TBARS). Novel and potentially therapeutic antioxidants have been prepared that combine the radical-scavenging ability of a myricetin-like head group with a lipophilic chain similar to that of vitamin E. C6-C12 alkyl chains are attached to the A-ring of either a 3,3′,4 ′,5′-tetrahydroxyflavone or a 3,2 ′,4′,5′-tetrahydroxyflavone head group to give lipophilic flavonoids (ClogP=4 to 10) that markedly inhibit iron-ADP catalysed oxidation of microsomal preparations. Orientation of the head group as well as total lipophilicity are important determinants of antioxidant efficacy. MM2 models indicate that our best straight chain 7-alkylflavonoids embed to the same depth in the membrane as vitamin E. The flavonoid head groups are prepared by aldol condensation followed by Algar-Flynn-Oyamada (AFO) oxidation or by Baker-Venkataraman rearrangement. The alkyl tails are introduced by Suzuki or Negishi palladium-catalysed cross-coupling or by cross-metathesis catalysed by first generation Grubbs catalyst, which tolerate phenolic hydroxyl and ketone groups.

FLAVONOID COMPOUNDS AS THERAPEUTIC ANTIOXIDANTS

Novel flavonoid compounds having anti-oxidant activity are described. The compounds have been shown to exhibit anti-oxidative properties in biological systems and their utility in a sunscreen or skincare composition or to treat conditions involving oxidative damage, especially curative or prophylactic treatment of Alzheimer's disease or ischaemia-reperfusion injury, is described.

Alumina in Methanesulfonic Acid (AMA) as a New Efficient Reagent for Direct Acylation of Phenol Derivatives and Fries Rearrangement. A Convenient Synthesis of o-Hydroxyarylketones

Alumina in methanesulfonic acid (AMA) is used to prepare o-hydroxyaryl ketones by acylation of phenol and naphthol derivatives with carboxylic acids and the Fries rearrangement of phenolic esters. Mechanistic studies show that the acylation reaction in AMA occurred through an esterification followed by a Fries rearrangement of the phenolic ester by an intermolecular mechanism.