4-(2-carboxybenzyloxy) phenyl acetic acid
isoxepac
Conditions | Yield |
---|---|
Stage #1: 4-(2-carboxybenzyloxy) phenyl acetic acid With trifluoroacetic anhydride In chlorobenzene at 20℃; for 4h; Stage #2: boron trifluoride diethyl etherate In chlorobenzene at -10 - 0℃; for 0.666667h; | 96.4% |
Stage #1: 4-(2-carboxybenzyloxy) phenyl acetic acid With trifluorormethanesulfonic acid; trifluoroacetic anhydride In toluene at 20 - 35℃; for 1h; Stage #2: With water In toluene | 71.3% |
With acetic anhydride at 80 - 90℃; for 2h; Large scale; | 69.9% |
Conditions | Yield |
---|---|
Stage #1: 4-hydroxyphenylacetate With potassium hydroxide In methanol at 20℃; for 1h; Friedel-Crafts Acylation; Stage #2: 2-(chloromethyl)benzoic acid In methanol Reflux; Stage #3: With Eaton′s Reagent at 80℃; for 2h; Reagent/catalyst; Solvent; Concentration; | 79.3% |
methyl 2-bromomethylbenzoate
isoxepac
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: K2CO3, KI / butan-2-one / 24 h / Heating 2: KOH / aq. ethanol / Heating 3: 1.) (CF3CO)2O, 2.) 10percent aq. HCl / 1.) CH2Cl2, reflux, 4 h, 2.) acetone, reflux, 24 h View Scheme |
(4-hydroxy-phenyl)-acetic acid ethyl ester
isoxepac
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: K2CO3, KI / butan-2-one / 24 h / Heating 2: KOH / aq. ethanol / Heating 3: 1.) (CF3CO)2O, 2.) 10percent aq. HCl / 1.) CH2Cl2, reflux, 4 h, 2.) acetone, reflux, 24 h View Scheme |
isoxepac
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: KOH / aq. ethanol / Heating 2: 1.) (CF3CO)2O, 2.) 10percent aq. HCl / 1.) CH2Cl2, reflux, 4 h, 2.) acetone, reflux, 24 h View Scheme |
4-benzyloxy-3-carboxyphenylacetic acid
isoxepac
Conditions | Yield |
---|---|
In methylene chloride-nitromethane; 4-benzyloxy-3-chlorocarbonylphenylacetyl chloride |
4-hydroxyphenylacetate
isoxepac
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium methylate / N,N-dimethyl-formamide; methanol / 120 - 135 °C 1.2: 5 - 10 °C 2.1: acetic acid / 2.5 h / 70 - 75 °C View Scheme |
2-benzofuran-1(3H)-one
isoxepac
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium methylate / N,N-dimethyl-formamide; methanol / 120 - 135 °C 1.2: 5 - 10 °C 2.1: acetic acid / 2.5 h / 70 - 75 °C View Scheme |
4-(2-methoxycarbonylbenzyloxy)phenyl acetic acid
isoxepac
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / ethanol / 3 h / Reflux; Large scale 1.2: pH 1 - 2 / Large scale 2.1: acetic anhydride / 2 h / 80 - 90 °C / Large scale View Scheme |
o-(chloromethyl)benzoic acid methyl ester
isoxepac
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / ethanol / 24 h / Reflux 2.1: potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / ethanol / 3 h / Reflux; Large scale 2.2: pH 1 - 2 / Large scale 3.1: acetic anhydride / 2 h / 80 - 90 °C / Large scale View Scheme |
Methyl 4-hydroxyphenylacetate
isoxepac
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / ethanol / 24 h / Reflux 2.1: potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / ethanol / 3 h / Reflux; Large scale 2.2: pH 1 - 2 / Large scale 3.1: acetic anhydride / 2 h / 80 - 90 °C / Large scale View Scheme |
isoxepac
11-hydroxy-2-(2-hydroxyethyl)-6,11-dihydrodibenz[b,e]oxepin
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Ambient temperature; | 98% |
isoxepac
benzyl alcohol
(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetic acid benzyl ester
Conditions | Yield |
---|---|
toluene-4-sulfonic acid In toluene Reflux; | 98% |
isoxepac
tert-butyl alcohol
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; di-tert-butyl dicarbonate; triethylamine In toluene at 50℃; for 8.5h; Reagent/catalyst; Solvent; Temperature; | 97% |
Stage #1: isoxepac With trifluoroacetic anhydride In toluene at 20℃; for 1h; Stage #2: tert-butyl alcohol In toluene at 20 - 80℃; for 4h; | 79.9% |
isoxepac
(Z)-11-(3-dimethylaminopropylidene)-6,11-dihydro-dibenz-[b,e]oxepine-2-acetic acid hydrobromide
Conditions | Yield |
---|---|
Stage #1: anhydrous 3-(dimethylamino)propyltriphenylphosphonium bromide hydrobromide With sodium hydride In tetrahydrofuran at 20 - 60℃; for 3.66667h; Stage #2: isoxepac In tetrahydrofuran at 10 - 25℃; for 20 - 30h; Wittig Reaction; Stage #3: With hydrogen bromide In 2-methyltetrahydrofuran; water; isopropyl alcohol pH=4.3 - 13.8; Product distribution / selectivity; | 96.95% |
Stage #1: (3-dimethylaminopropyl)-triphenylphosphoniumbromide With sodium hydride In tetrahydrofuran at 20 - 60℃; for 2.5h; Stage #2: isoxepac In tetrahydrofuran at 15 - 25℃; for 40h; Wittig Reaction; Stage #3: With hydrogen bromide In water; butan-1-ol at 0 - 25℃; pH=4.2 - 12.59; Product distribution / selectivity; | 53.5% |
isoxepac
isopropyl alcohol
(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetic acid isopropyl ester
Conditions | Yield |
---|---|
toluene-4-sulfonic acid Reflux; | 96% |
methanol
isoxepac
methyl 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetate
Conditions | Yield |
---|---|
With tert.-butylnitrite at 40℃; for 48h; | 96% |
With thionyl chloride at 0 - 20℃; for 24.5h; | |
With thionyl chloride at 0 - 25℃; for 24.5h; |
isoxepac
ethanol
ethyl 2-(11-oxo-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 2h; Reflux; | 94% |
toluene-4-sulfonic acid Reflux; | 93% |
isoxepac
butan-1-ol
(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetic acid butyl ester
Conditions | Yield |
---|---|
With sulfuric acid at 115℃; | 93% |
With sulfuric acid at 115℃; for 2h; Dean Stark apparatus; | 93% |
isoxepac
olopatadine hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-(3-chloropropyl)-N,N-dimethylamine hydrochloride With potassium bromide for 1h; Inert atmosphere; Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide In dimethyl sulfoxide for 2h; Reflux; Stage #3: isoxepac In dimethyl sulfoxide at 20℃; for 1h; Reagent/catalyst; Solvent; | 90.5% |
isoxepac
Cyclopropylamine
Conditions | Yield |
---|---|
Stage #1: isoxepac With 1,1'-carbonyldiimidazole In dichloromethane for 1h; Stage #2: Cyclopropylamine In dichloromethane at 20℃; for 2h; | 90% |
Stage #1: isoxepac With 1,1'-carbonyldiimidazole In dichloromethane for 1h; Stage #2: Cyclopropylamine In dichloromethane at 20℃; for 2h; | 90% |
isoxepac
1-bromo-3-propanol
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere; | 89% |
isoxepac
6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-carboxaldehyde
Conditions | Yield |
---|---|
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; 1-λ3-benzo[d][1,2]iodaoxol-3(1H)-one In 2,2,2-trifluoroethanol at 40℃; for 3h; UV-irradiation; | 86% |
With oxygen; copper diacetate In dimethyl sulfoxide at 120℃; |
Conditions | Yield |
---|---|
Stage #1: isoxepac With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: monomethyl monopotassium malonate With magnesium chloride In dichloromethane at 20℃; for 24h; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
Stage #1: isoxepac With potassium carbonate; trichlorophosphate In water; chlorobenzene at 40℃; Stage #2: isobutene In water; chlorobenzene at 40℃; for 8h; Product distribution / selectivity; | 85.3% |
isoxepac
hex-5-en-3-yn-1-ol
Conditions | Yield |
---|---|
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere; Schlenk technique; | 84% |
isoxepac
2-(chloromethyl)dibenzo[b,e]oxepin-11(6H)-one
Conditions | Yield |
---|---|
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; dibenzenesulfonamide; 1-λ3-benzo[d][1,2]iodaoxol-3(1H)-one; tetrabutyl-ammonium chloride In dichloromethane at 40℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; | 82% |
isoxepac
(4-vinyl-phenyl)-methanol
Conditions | Yield |
---|---|
With dmap; diisopropyl-carbodiimide In dichloromethane | 82% |
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-3-bromopropylamine With zinc dibromide In tetrahydrofuran at 10 - 20℃; for 0.166667h; Inert atmosphere; Stage #2: With naphthalene; lithium In tetrahydrofuran at 65 - 70℃; Inert atmosphere; Stage #3: isoxepac In tetrahydrofuran at 0 - 25℃; for 16.5h; Reagent/catalyst; Temperature; | 81.2% |
isoxepac
2,2,2-trifluoroethanol
Conditions | Yield |
---|---|
With thionyl chloride; triethylamine at 0 - 40℃; for 12.3333h; Inert atmosphere; | 80% |
N-hydroxyphthalimide
isoxepac
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 80% |
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 1h; | 71% |
With dmap; diisopropyl-carbodiimide In dichloromethane |
isoxepac
Conditions | Yield |
---|---|
With dmap; copper diacetate In acetonitrile at 80℃; for 3h; Schlenk technique; Sealed tube; | 80% |
3-(N,N-dimethylamino)propylmagnesium chloride
isoxepac
Conditions | Yield |
---|---|
Stage #1: 3-(N,N-dimethylamino)propylmagnesium chloride; isoxepac In tetrahydrofuran; toluene at 5 - 18℃; for 2.08333h; Stage #2: With water; acetic acid In tetrahydrofuran; toluene | 79.7% |
isoxepac
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 12.5h; Inert atmosphere; | 79% |
isoxepac
methylamine hydrochloride
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane | 78% |
isoxepac
dibenzenesulfonamide
Conditions | Yield |
---|---|
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; 1-λ3-benzo[d][1,2]iodaoxol-3(1H)-one In dichloromethane at 40℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; | 75% |
isoxepac
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; | 72% |
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 20℃; for 2h; | 72% |
isoxepac
6,11-dihydro-11-oxodibenz[b,e]oxepin-2-carboxylic acid
Conditions | Yield |
---|---|
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; [bis(acetoxy)iodo]benzene; oxygen In 2,2,2-trifluoroethanol for 24h; UV-irradiation; | 70% |
Molecular structure of Isoxepac (CAS NO.55453-87-7) is:
Product Name: Isoxepac
CAS Registry Number: 55453-87-7
IUPAC Name: 2-(11-oxo-6H-benzo[c][2]benzoxepin-2-yl)acetic acid
Molecular Weight: 268.26408 [g/mol]
Molecular Formula: C16H12O4
XLogP3: 2.4
H-Bond Donor: 1
H-Bond Acceptor: 4
Surface Tension: 58.8 dyne/cm
Density: 1.349 g/cm3
Flash Point: 203.8 °C
Enthalpy of Vaporization: 84.52 kJ/mol
Boiling Point: 528.2 °C at 760 mmHg
Vapour Pressure: 5.51E-12 mmHg at 25°C
Product Categories: APIs Intermediate
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 240mg/kg (240mg/kg) | GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 227, Pg. 142, 1977. |
mouse | LD50 | oral | 500mg/kg (500mg/kg) | GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 227, Pg. 142, 1977. |
rabbit | LD50 | oral | 160mg/kg (160mg/kg) | GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 227, Pg. 142, 1977. |
rat | LD50 | oral | 143mg/kg (143mg/kg) | GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 227, Pg. |
Isoxepac , its cas register number is 55453-87-7. It also can be called 6,11-Dihydro-11-oxodibenz(b,e)oxepin-2-acetic acid ; Arelix ; Artil ; Dibenz(b,e)oxepin-2-acetic acid, 6,11-dihydro-11-oxo- ; Isoxepacum [INN-Latin] .It is a light-yellow to pale-white crystalline powder.
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