A
metyrapone
B
3,3-di-pyridin-3-yl-butan-2-one
C
3,3'-(1,2-bis-methylene-ethane-1,2-diyl)-bis-pyridine
Conditions | Yield |
---|---|
With sulfuric acid for 70h; Further byproducts given; | A 22% B 38% C 13% D 14% |
2,3-di-3-pyridyl-2,3-butanediol
A
metyrapone
B
3,3-di-pyridin-3-yl-butan-2-one
Conditions | Yield |
---|---|
With sulfuric acid |
A
metyrapone
B
3,3-di-pyridin-3-yl-butan-2-one
Conditions | Yield |
---|---|
With sulfuric acid at 23℃; Product distribution; Further Variations:; Reagents; |
A
metyrapone
B
3,3'-(1,2-bis-methylene-ethane-1,2-diyl)-bis-pyridine
Conditions | Yield |
---|---|
With sulfuric acid at 23℃; Product distribution; Further Variations:; Reagents; Temperatures; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: isopropyl alcohol; acetic acid / Einwirkung von UV-Licht 2: concentrated H2SO4 View Scheme |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In tetrahydrofuran for 3.5h; Inert atmosphere; Reflux; |
acetonitrile
A
metyrapone
B
bis(acetonitrile)bis(2,2'-bipyridine)ruthenium(II) hexafluorophosphate
Conditions | Yield |
---|---|
for 1h; Kinetics; Time; UV-irradiation; |
Conditions | Yield |
---|---|
for 0.0166667h; Kinetics; Time; UV-irradiation; |
metyrapone
Metyrapol
Conditions | Yield |
---|---|
With sodium tetrahydroborate Reduction; | 100% |
With sodium tetrahydroborate In methanol Reduction; | |
With human liver dihydrodiol dehydrogenase 4; NADPH In phosphate buffer at 25℃; pH=6.0; Enzyme kinetics; Further Variations:; Reagents; |
metyrapone
Conditions | Yield |
---|---|
With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In 1,4-dioxane for 14h; Minisci Aromatic Substitution; Irradiation; enantioselective reaction; | 70% |
metyrapone
triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
Conditions | Yield |
---|---|
With 1,2-dimethoxyethane; potassium hexamethylsilazane for 3h; Inert atmosphere; regioselective reaction; | 54% |
Conditions | Yield |
---|---|
With tert-Butyl peroxybenzoate In dichloromethane at 20℃; for 12h; Catalytic behavior; Irradiation; Inert atmosphere; | 46% |
potassium hexafluorophosphate
metyrapone
Conditions | Yield |
---|---|
Stage #1: metyrapone; bis(2,2'-bipyridine)dichlororuthenium(II) dihydrate In water at 80℃; Inert atmosphere; Stage #2: potassium hexafluorophosphate In water | 38% |
metyrapone
A
3-(1-methylethenyl)pyridine
B
3-isopropylpyridine
C
nicotinic acid
D
2-(3-pyridinyl)-2-propanol
F
2,3-di(3-pyridyl)-2,3-dimethylbutane
Conditions | Yield |
---|---|
With 1-dodecylthiol In cyclohexane Quantum yield; Product distribution; Irradiation; | A 4% B 6% C 15% D 15% E n/a F 35% |
metyrapone
A
3-(1-methylethenyl)pyridine
B
3-isopropylpyridine
C
2-(3-pyridinyl)-2-propanol
D
2,3-di(3-pyridyl)-2,3-dimethylbutane
Conditions | Yield |
---|---|
In methanol for 6h; Irradiation; | A 4% B 2% C 2% D 35% |
Conditions | Yield |
---|---|
In neat (no solvent) for 40h; Product distribution; Mechanism; Irradiation; also in MeCN solution; | A 30% B 11% C 6% D 3% E 4% |
metyrapone
B
2-Methyl-1-<3'-(1'-oxopyridyl)>-2-(3''-pyridyl)-propan-1-one
C
2-Methyl-2-<3''-(1''-oxopyridyl)>-1-(3'-pyridyl)-propan-1-one
D
2-Methyl-1,2-bis-3-(1-oxopyridyl)propan-1-one
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In chloroform for 0.0833333h; -10 deg C to r.t.; Yield given. Yields of byproduct given; | |
With 3-chloro-benzenecarboperoxoic acid In chloroform 1.) -10 deg C to r.t., 2.) r.t., 5 min; Yield given. Yields of byproduct given; |
metyrapone
Conditions | Yield |
---|---|
1.) H2O, irrad., 6 h, 2.) heating; Yield given. Multistep reaction; |
metyrapone
Conditions | Yield |
---|---|
With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; triphenylphosphine; sodium iodide In 1,4-dioxane at 20℃; for 20h; Schlenk technique; Inert atmosphere; Irradiation; Overall yield = 55 %; | A n/a B n/a |
With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; triphenylphosphine; sodium iodide In 1,4-dioxane at 20℃; for 15h; Irradiation; Overall yield = 55 %; enantioselective reaction; | A n/a B n/a |
Conditions | Yield |
---|---|
With rose bengal In dimethyl sulfoxide at 20℃; Irradiation; Overall yield = 33 percent; |
Product Name: Metyrapone (CAS NO.54-36-4)
Molecular Formula: C14H14N2O
Molecular Weight: 226.27g/mol
Mol File: 54-36-4.mol
Einecs: 200-206-2
Melting Point: 52-55 °C(lit.)
Boiling point: 384.4 °C at 760 mmHg
Flash Point: 189.3 °C
Density: 1.12 g/cm3
Surface Tension: 45.4 dyne/cm
Enthalpy of Vaporization: 63.3 kJ/mol
Vapour Pressure: 4.11E-06 mmHg at 25°C
XLogP3-AA: 2
H-Bond Donor: 0
H-Bond Acceptor: 3
Structure Descriptors of Metyrapone (CAS NO.54-36-4):
IUPAC Name: 2-methyl-1,2-dipyridin-3-ylpropan-1-one
Canonical SMILES: CC(C)(C1=CN=CC=C1)C(=O)C2=CN=CC=C2
InChI: InChI=1S/C14H14N2O/c1-14(2,12-6-4-8-16-10-12)13(17)11-5-3-7-15-9-11/h3-10H,1-2H3
InChIKey: FJLBFSROUSIWMA-UHFFFAOYSA-N
Product Categories: Cytochrome P450 isozyme
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | subcutaneous | 531mg/kg (531mg/kg) | Cesko-Slovenska Farmacie. Vol. 26, Pg. 140, 1977. | |
mouse | LDLo | intraperitoneal | 300mg/kg (300mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 146, Pg. 395, 1964. | |
rat | LD50 | oral | 521mg/kg (521mg/kg) | Drugs in Japan Vol. 6, Pg. 827, 1982. |
Poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Safety Information of Metyrapone (CAS NO.54-36-4):
Hazard Codes: Xn
Risk Statements: 22-36/37/38
22: Harmful if swallowed
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements: 26
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
Metyrapone ,its CAS NO. is 54-36-4,the synonyms is 1,2-Di-3-pyridyl-2-methyl-1-propanone ; 1-Propanone, 1,2-di-3-pyridyl-2-methyl- ; 1-Propanone, 2-methyl-1,2-di-3-pyridinyl- ; 2-Methyl-1,2-bis(3-pyridyl)-1-propanone ; 2-Methyl-1,2-di-3-pyridyl-1-propanone ; EINECS 200-206-2 ; HSDB 2500 ; Methapyrapone ; Metyraponum ; NSC 25265 ; UNII-ZS9KD92H6V .
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