fenofibrate
fenofibric acid
Conditions | Yield |
---|---|
With water; triethylamine; lithium bromide In acetonitrile for 7h; Heating; | 99% |
With iodine; aluminium In acetonitrile at 80℃; for 18h; | 97% |
With sodium hydroxide In methanol at 69.85℃; for 4h; | 85% |
benzyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
fenofibric acid
Conditions | Yield |
---|---|
Stage #1: benzyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate With potassium hydroxide In ethanol for 16h; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1; | 91% |
2-bromo-2-methylpropionic acid
4-chloro-4'-hydroxybenzophenone
fenofibric acid
Conditions | Yield |
---|---|
Stage #1: 4-chloro-4'-hydroxybenzophenone With sodium hydroxide In butanone at 50℃; for 1h; Stage #2: 2-bromo-2-methylpropionic acid In butanone at 50℃; for 16h; | 87% |
Multistep reaction.; |
chloroform
4-chloro-4'-hydroxybenzophenone
acetone
fenofibric acid
Conditions | Yield |
---|---|
Stage #1: 4-chloro-4'-hydroxybenzophenone; acetone With sodium hydroxide for 2h; Heating / reflux; Stage #2: chloroform In acetone for 8h; Heating / reflux; | 73% |
With sodium hydroxide | |
With sodium hydroxide |
chloroform
2-(4-iodophenoxy)-2-methylpropanoic acid
4-Chlorophenylboronic acid
fenofibric acid
Conditions | Yield |
---|---|
With cesiumhydroxide monohydrate; sodium carbonate; sodium iodide; Trimethylacetic acid In ethylene glycol at 120℃; for 48h; Sealed tube; Green chemistry; | 72% |
2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic acid ethyl ester
fenofibric acid
Conditions | Yield |
---|---|
With water; sodium hydroxide In ethanol at 25℃; Temperature; | 0.95 g |
4-chloro-benzoyl chloride
fenofibric acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aluminium trichloride 2: sodium hydroxide View Scheme | |
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / toluene / 1.5 h / 0 °C / Inert atmosphere; Reflux 2.1: sodium hydroxide / butanone / 1 h / Reflux 2.2: 8 h / Reflux 3.1: sodium hydroxide / 4 h / Reflux View Scheme |
methoxybenzene
fenofibric acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aluminium trichloride 2: sodium hydroxide View Scheme | |
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / toluene / 1.5 h / 0 °C / Inert atmosphere; Reflux 2.1: sodium hydroxide / butanone / 1 h / Reflux 2.2: 8 h / Reflux 3.1: sodium hydroxide / 4 h / Reflux View Scheme |
chlorosulfuric acid chloromethyl ester
fenofibric acid
chloromethyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate
Conditions | Yield |
---|---|
Stage #1: fenofibric acid With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In water at 20℃; for 0.25h; Stage #2: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 20℃; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
With magneticnanosolidsuperacid In cyclohexane; water at 83 - 85℃; Reagent/catalyst; Temperature; | 97% |
Stage #1: fenofibric acid; isopropyl alcohol With thionyl chloride for 7h; Reflux; Stage #2: With potassium carbonate In water at 60 - 65℃; | 96.6% |
With macroporous strong acid cation exchange resin D001 In water; toluene at 110℃; | 92.4% |
fenofibric acid
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 25℃; for 16h; Catalytic behavior; Irradiation; Inert atmosphere; Sealed tube; | 97% |
1,3-bis(2,2-dimethyl-1,3-dioxan-5-yloxy)propan-2-yl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate
fenofibric acid
1,3-bis(2,2-dimethyl-1,3-dioxan-5-yloxy)propan-2-yl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
Stage #1: fenofibric acid With potassium carbonate In Isopropyl acetate; dimethyl sulfoxide at 20 - 90℃; for 0.75h; Industry scale; Inert atmosphere; Stage #2: isopropyl bromide In Isopropyl acetate; dimethyl sulfoxide at 80 - 95℃; for 5.83333h; | 94.9% |
fenofibric acid
2-(4-((4-chlorophenyl)(hydroxy)methyl)phenoxy)-2-methylpropan-1-ol
Conditions | Yield |
---|---|
Stage #1: fenofibric acid With borane-THF In tetrahydrofuran at 0 - 50℃; for 3h; Inert atmosphere; Stage #2: With methanol In tetrahydrofuran at 0℃; | 94% |
With borane-THF In tetrahydrofuran at 0 - 50℃; for 3h; Inert atmosphere; | 94% |
fenofibric acid
Conditions | Yield |
---|---|
With 2,4,6-trimethyl-pyridine; 2,4,6-Triisopropylthiophenol; water-d2; 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane for 16h; Irradiation; | 94% |
fenofibric acid
4-chloromethyl-5-methyl-1,3-dioxol-2-one
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl-2‑(4‑(4-chlorobenzoyl)phenoxy)-2-methylpropanoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl acetamide at 65℃; | 93% |
With sodium carbonate In N,N-dimethyl acetamide at 30℃; for 17h; Inert atmosphere; | 83% |
fenofibric acid
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl acetamide at 65℃; | 93% |
fenofibric acid
2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanamide
Conditions | Yield |
---|---|
With ammonium hydroxide In tetrahydrofuran at 20℃; for 1h; | 93% |
fenofibric acid
benzyl glycolate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; | 92.31% |
fenofibric acid
2-[4-(4-chlorobenzoyl)-phenoxy]-2-methylpropionyl chloride
Conditions | Yield |
---|---|
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 3h; | 91.4% |
With thionyl chloride In Petroleum ether; benzene | 83.2% |
With thionyl chloride In benzene Heating; |
fenofibric acid
N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester
C29H36ClNO8
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 20h; | 87% |
Conditions | Yield |
---|---|
With 9-mesityl-2,7-dimethyl-10-phenylacridin-10-ium tetrafluoroborate; potassium carbonate at 20℃; Inert atmosphere; Irradiation; diastereoselective reaction; | 87% |
N-hydroxyphthalimide
fenofibric acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere; | 86% |
In dichloromethane |
fenofibric acid
iodomethyl pivaloate
2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic acid pivaloyloxymethyl ester
Conditions | Yield |
---|---|
Stage #1: fenofibric acid With N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at -5℃; for 0.333333h; Inert atmosphere; Stage #2: iodomethyl pivaloate In N,N-dimethyl acetamide at -5℃; for 0.25h; Inert atmosphere; | 85% |
fenofibric acid
1-iodoethyl isopropyl carbonate
2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic acid 1-isopropoxy carbonyloxyethyl ester
Conditions | Yield |
---|---|
Stage #1: fenofibric acid With N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at -5℃; for 0.333333h; Inert atmosphere; Stage #2: 1-iodoethyl isopropyl carbonate In N,N-dimethyl acetamide at -5℃; for 0.75h; Inert atmosphere; | 85% |
2-chloro-1-acetoxyethane
fenofibric acid
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl acetamide at 65℃; | 85% |
(2-hydroxyethyl)(methyl)amine
fenofibric acid
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 85% |
isopropyloxycarbonyloxymethyl iodide
fenofibric acid
2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic acid isopropoxycarbonyl oxymethyl ester
Conditions | Yield |
---|---|
Stage #1: fenofibric acid With N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at 0℃; for 0.333333h; Inert atmosphere; Stage #2: isopropyloxycarbonyloxymethyl iodide In N,N-dimethyl acetamide at 0℃; for 0.5h; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
With tert-Amyl alcohol; t-Boc-L-valine; oxygen; palladium diacetate; potassium hydrogencarbonate at 90℃; for 24h; Schlenk technique; | 83% |
fenofibric acid
N-(tert-butyloxycarbonyl)-L-threonine tert-butyl ester
C30H38ClNO8
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 96h; | 82% |
fenofibric acid
2-Aminoacetophenone
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; | 82% |
morpholine-4-carboxylic acid 2-chloro-ethyl ester
fenofibric acid
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl acetamide at 65℃; | 82% |
Conditions | Yield |
---|---|
With sodium hydroxide In water | 82% |
Conditions | Yield |
---|---|
Stage #1: fenofibric acid With sodium hydroxide In water Stage #2: berberine chloride In water Solvent; Temperature; Heating; | 82% |
N-(2-chlorethyl)morpholine
fenofibric acid
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl acetamide at 65℃; | 81% |
Fenofibric acid increased transcription of ABCA1 gene in a liver X receptor–dependent manner. Fibrates are widely used drugs to reduce plasma triglyceride and increase high-density lipoprotein. Their active forms, fibric acids, are peroxisome proliferator-activated receptor- activators, but no direct evidence has been demonstrated for their activation of ATP-binding cassette transporter A1 (ABCA1) in relation to clinically used fibrates. We investigated the reaction of fenofibric acid in this regard, finding that fenofibric acid increased transcription of ABCA1 gene in n liver X receptor–dependent manner.
The Fenofibric acid belongs to the product categories of Pharmacetical; Various Metabolites and Impurities; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals; Aromatics. Its EINECS number is 255-626-9. What's more, its systematic name is 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic acid. Its classification codes are: (1)Anticholesteremic Agents; (2)Antilipemic agents; (3)Antimetabolites; (4)Drug / Therapeutic Agent. This chemical is used as pharmaceutical intermediates and intermediate of fenofibrate. It is the active metabolite of fenofibrate.
Physical properties of Fenofibric acid are:
(1)ACD/LogP: 3.992; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.60; (4)ACD/LogD (pH 7.4): 0.35; (5)ACD/BCF (pH 5.5): 2.55; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 14.17; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 63.6 Å2; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 83.048 cm3; (15)Molar Volume: 247.696 cm3; (16)Polarizability: 32.923×10-24cm3; (17)Surface Tension: 49.10 dyne/cm; (18)Density: 1.287 g/cm3; (19)Flash Point: 248.001 °C; (20)Enthalpy of Vaporization: 79.223 kJ/mol; (21)Boiling Point: 486.457 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
Safety Information of Fenofibric acid:
When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection.
You could convert the following datas into the molecular structure:
(1)SMILES: O=C(c1ccc(Cl)cc1)c2ccc(OC(C(=O)O)(C)C)cc2
(2)Std. InChI: InChI=1S/C17H15ClO4/c1-17(2,16(20)21)22-14-9-5-12(6-10-14)15(19)11-3-7-13(18)8-4-11/h3-10H,1-2H3,(H,20,21)
(3)Std. InChIKey: MQOBSOSZFYZQOK-UHFFFAOYSA-N
Toxicity of Fenofibric acid are as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 500mg/kg (500mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 885, 1976. | |
mouse | LD50 | oral | 1200mg/kg (1200mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 885, 1976. | |
rat | LD50 | intravenous | 313mg/kg (313mg/kg) | LUNGS, THORAX, OR RESPIRATION: PLEURAL THICKENING BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 23. |
rat | LD50 | oral | 1242mg/kg (1242mg/kg) | Drugs of the Future. Vol. 7, Pg. 229, 1982. |
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