Conditions | Yield |
---|---|
Stage #1: tiolacetic acid With trifluoromethylsulfonic anhydride In tetrahydrofuran Stage #2: canrenone In tetrahydrofuran at 20℃; for 1h; | 76% |
With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 3h; | 60% |
In water at 20℃; for 2h; Michael addition; |
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran for 1h; Ambient temperature; Yields of byproduct given; | A n/a B 64% |
With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran for 1h; Ambient temperature; Yield given; | A n/a B 64% |
Conditions | Yield |
---|---|
In toluene |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating 2: 64 percent / TMSOTf / tetrahydrofuran / 1 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: tetrachloro-<1,4>benzoquinone; xylene; toluene-4-sulfonic acid-monohydrate View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 98 percent / trimethyl orthoformate, p-toluenesulfonic acid / methanol / 3 h / 50 °C 2: H2, triphenylphosphine, rhodium acetate dimer / ethyl acetate / 20 h / 80 °C / 9000.7 Torr 3: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h 4: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h 5: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating 6: 64 percent / TMSOTf / tetrahydrofuran / 1 h / Ambient temperature View Scheme |
17α-ethynyl-17β-hydroxy-5-androsten-3-one ethylene ketal
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: H2, triphenylphosphine, rhodium acetate dimer / ethyl acetate / 20 h / 80 °C / 9000.7 Torr 2: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h 3: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h 4: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating 5: 64 percent / TMSOTf / tetrahydrofuran / 1 h / Ambient temperature View Scheme |
5'-hydroxyspiro-5-en-3-one
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h 2: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h 3: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating 4: 64 percent / TMSOTf / tetrahydrofuran / 1 h / Ambient temperature View Scheme |
C24H34O4
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h 2: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating 3: 64 percent / TMSOTf / tetrahydrofuran / 1 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: lithium bromide; C30H31Cl3N3(1+)*BF4(1-); triethylamine / 1,2-dichloro-ethane / 5 h / 20 °C / Inert atmosphere; Sealed tube 2.1: chloranil / 1,2-dichloro-ethane; methanol; water / 1 h / 20 °C 3.1: trifluoromethylsulfonic anhydride / tetrahydrofuran 3.2: 1 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: iodine; mercury dichloride; magnesium / diethyl ether / 0.5 h / 40 °C 1.2: 2.5 h / 0 - 20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C 2.2: 2 h / 0 - 20 °C 2.3: 1 h / 0 - 20 °C 3.1: Dess-Martin periodane / dichloromethane / 4 h / 0 - 20 °C 4.1: chloranil / tert-butyl alcohol / 3 h / 80 °C 5.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 3 h / 20 °C View Scheme |
21,24-dinor-3β,17β-dihydroxy-chol-5-en-22-yne
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C 1.2: 2 h / 0 - 20 °C 1.3: 1 h / 0 - 20 °C 2.1: Dess-Martin periodane / dichloromethane / 4 h / 0 - 20 °C 3.1: chloranil / tert-butyl alcohol / 3 h / 80 °C 4.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 3 h / 20 °C View Scheme |
3β,17β-Dihydroxy-5-androsten-17α-propanoic Acid γ-Lactone
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Dess-Martin periodane / dichloromethane / 4 h / 0 - 20 °C 2: chloranil / tert-butyl alcohol / 3 h / 80 °C 3: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 3 h / 20 °C View Scheme |
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: chloranil / tert-butyl alcohol / 3 h / 80 °C 2: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 3 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With mercury dichloride In ethanol Ambient temperature; | 95% |
With sodium methylate In tetrahydrofuran at 20℃; for 18h; Elimination; | 72% |
With potassium dihydrogenphosphate In ethanol at 40℃; Rate constant; Kinetics; Thermodynamic data; var. buffers, pH, temp., ionic strengh, spironolactone and buffer conc.; energy of activation; |
SPIRONOLACTONE
Conditions | Yield |
---|---|
With pyridinium hydrobromide perbromide In acetic acid for 1.5h; Ambient temperature; | 87% |
SPIRONOLACTONE
3-(3-oxo-7α-thio-17β-hydroxy-4-androsten-17α-yl)propionic acid γ-lactone
Conditions | Yield |
---|---|
Stage #1: SPIRONOLACTONE With sodium methylate In methanol at 20℃; for 0.666667h; Stage #2: With acetic acid In methanol; water pH=7; | 69% |
With β‐cyclodextrin In phosphate buffer at 25℃; pH=7.0; Deacetylation; | |
With sodium methylate In methanol for 0.666667h; Inert atmosphere; Cooling with ice; |
SPIRONOLACTONE
Conditions | Yield |
---|---|
With sodium tetrahydroborate; activated acidic alumina Brockmann II In ethyl acetate at 20℃; for 2h; | 66% |
Conditions | Yield |
---|---|
With mercury dichloride In ethanol for 2h; Heating; | A 38% B 54% |
Conditions | Yield |
---|---|
for 5h; Heating; | 44% |
SPIRONOLACTONE
β‐cyclodextrin
2C42H70O35*C24H32O4S
Conditions | Yield |
---|---|
In water-d2 Product distribution; |
Conditions | Yield |
---|---|
In dimethylsulfoxide-d6 Product distribution; |
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / sodium methoxide / tetrahydrofuran / 18 h / 20 °C 2: 59 percent / sodium metal / 24 h / 60 °C View Scheme |
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / sodium methoxide / tetrahydrofuran / 18 h / 20 °C 2: 72 percent / sodium metal / 24 h / 60 °C View Scheme |
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / sodium methoxide / tetrahydrofuran / 18 h / 20 °C 2: 59 percent / sodium metal / 24 h / 60 °C View Scheme |
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / sodium methoxide / tetrahydrofuran / 18 h / 20 °C 2: 74 percent / sodium metal / 24 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium methylate / methanol / 0.67 h / 20 °C 1.2: pH 7 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2 h / 80 °C View Scheme |
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / sodium methoxide / tetrahydrofuran / 18 h / 20 °C 2: 62 percent / sodium metal / 24 h / 60 °C View Scheme |
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / sodium methoxide / tetrahydrofuran / 18 h / 20 °C 2: 40 percent / 3 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium methylate / methanol / 0.67 h / 20 °C 1.2: pH 7 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 80 °C View Scheme |
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 72 percent / sodium methoxide / tetrahydrofuran / 18 h / 20 °C 2: 91 percent / sodium / 0.75 h / 45 °C 3: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.75 h / -78 °C View Scheme |
SPIRONOLACTONE
3-oxo-17α-pregna-4-ene-7α-[4-(t-butyldimethylsilyloxy)-benzylthia]-21,17-carbolactone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / sodium methoxide / tetrahydrofuran / 18 h / 20 °C 2: 91 percent / sodium / 0.75 h / 45 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium methylate / methanol / 0.67 h / 20 °C 1.2: pH 7 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2 h / 60 °C View Scheme |
SPIRONOLACTONE
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / sodium methoxide / tetrahydrofuran / 18 h / 20 °C 2: 82 percent / sodium / 1 h / 45 °C View Scheme |
The Spironolactone, with the cas registry number 52-01-7, has the IUPAC name of S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate. This is a kind of white to off white solid, and is practically insoluble. Its product categories are including Active Pharmaceutical Ingredients; Biochemistry; Steroids; Steroids (Others); Intermediates & Fine Chemicals; Pharmaceuticals; API's. As to its usage, it is a kind of diuretic and also used as an antiandrogen.
The physical properties of this chemical are as follows: (1)ACD/LogP: 3.12; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.12; (4)ACD/LogD (pH 7.4): 3.12; (5)ACD/BCF (pH 5.5): 139.34; (6)ACD/BCF (pH 7.4): 139.34; (7)ACD/KOC (pH 5.5): 1192.14; (8)ACD/KOC (pH 7.4): 1192.14; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 85.74; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 112.68 cm3; (15)Molar Volume: 335.7 cm3; (16)Polarizability: 44.67 ×10-24 cm3; (17)Surface Tension: 50.8 dyne/cm; (18)Density: 1.24 g/cm3; (19)Flash Point: 302.3 °C; (20)Enthalpy of Vaporization: 88.93 kJ/mol; (21)Boiling Point: 597 °C at 760 mmHg; (22)Vapour Pressure: 3.24E-14 mmHg at 25°C; (23)Exact Mass: 416.20213; (24)MonoIsotopic Mass: 416.20213; (25)Topological Polar Surface Area: 85.7; (26)Heavy Atom Count: 29; (27)Formal Charge: 0; (28)Complexity: 818.
When you are dealing with this chemical, you should be very cautious. For being a kind of irritant chemical to eyes, respiratory system and skin, it may cause inflammation to the skin or other mucous membranes. Then it is harmful which may cause damage to health. What's more, it is even toxic which could at low levels cause damage to health. This chemical may have impair fertility and may have limited evidence of a carcinogenic effect.
Therefore, you should take the following instructions to protect yourself. Wear suitable protective clothing, gloves and eye/face protection and avoid exposure - obtain special instructions before use. If in case of accident or if you feel unwell seek medical advice immediately (show the label where possible), and if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Then do remember not breathe dust. When store it, keep in a dry, cool and well-ventilated place, away from the food raw material.
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(=O)SC1CC2=CC(=O)CCC2(C3C1C4CCC5(C4(CC3)C)CCC(=O)O5)C
(2)Isomeric SMILES: CC(=O)S[C@@H]1CC2=CC(=O)CC[C@@]2([C@@H]3[C@@H]1[C@@H]4CC[C@]5([C@]4(CC3)C)CCC(=O)O5)C
(3)InChI: InChI=1S/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19+,21+,22-,23-,24+/m0/s1
(4)InChIKey: LXMSZDCAJNLERA-ZHYRCANASA-N
Below are the toxicity information of this chemical:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
human | TDLo | oral | 5600mg/kg (5600mg/kg) | KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED | Journal of Laboratory and Clinical Medicine. Vol. 80, Pg. 224, 1972. |
man | TDLo | oral | 5714ug/kg/4D- (5.714mg/kg) | LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)" BLOOD: AGRANULOCYTOSIS BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED) | Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 974, 1987. |
man | TDLo | oral | 7500ug/kg/3W- (7.5mg/kg) | BLOOD: AGRANULOCYTOSIS | Australian and New Zealand Journal of Medicine. Vol. 30, Pg. 515, 2000. |
man | TDLo | oral | 7500ug/kg/3W- (7.5mg/kg) | BLOOD: AGRANULOCYTOSIS BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE | Australian and New Zealand Journal of Medicine. Vol. 30, Pg. 515, 2000. |
mouse | LD50 | intraperitoneal | 260mg/kg (260mg/kg) | Drugs in Japan Vol. 6, Pg. 381, 1982. | |
mouse | LD50 | intravenous | 260mg/kg (260mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967. | |
mouse | LD50 | oral | > 1gm/kg (1000mg/kg) | Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978. | |
rabbit | LD50 | intraperitoneal | 866mg/kg (866mg/kg) | Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978. | |
rabbit | LD50 | oral | > 1gm/kg (1000mg/kg) | Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978. | |
rat | LD50 | intraperitoneal | 277mg/kg (277mg/kg) | Drugs in Japan Vol. 6, Pg. 381, 1982. | |
rat | LD50 | oral | > 1gm/kg (1000mg/kg) | Drugs in Japan Vol. 6, Pg. 381, 1982. | |
women | TDLo | oral | 70mg/kg/5W-I (70mg/kg) | BLOOD: AGRANULOCYTOSIS | British Medical Journal. Vol. 289, Pg. 731, 1984. |
women | TDLo | oral | 122mg/kg/61D- (122mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | New Zealand Medical Journal. Vol. 83, Pg. 147, 1976. |
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