3β-acetoxy-20-hydroxyiminopregna-5,16-diene
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With Dess-Martin periodane In dichloromethane; water for 0.333333h; | 95% |
(3β)-21-bromo-20-oxopregna-5,16-dien-3-yl acetate
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With aluminum oxide; zirconium(IV) chloride; benzaldehyde microwave irradiation; | 88% |
3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate
ethyl vinyl ether
A
(Z/E)-3β-Acetoxypregna-5,17(20)-dien-21-al
B
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); triethylamine In dimethyl sulfoxide at 60℃; for 4h; | A 8% B 82% |
Tributyl-[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-stannane
acetyl chloride
A
3β-acetoxyandrost-5,16-diene
B
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; bis(benzonitrile)palladium(II) dichloride at 80℃; for 8h; | A 80% B 30% |
Conditions | Yield |
---|---|
80% |
Conditions | Yield |
---|---|
Stage #1: solasodine With pyridine; ammonium chloride at 125 - 135℃; for 8 - 9h; Stage #2: acetic acid With chromium(VI) oxide In water; 1,2-dichloro-ethane at 0 - 20℃; for 1h; Product distribution / selectivity; | 65% |
Conditions | Yield |
---|---|
With chromium(VI) oxide; acetic acid | 41% |
Stage #1: pseudodiosgenin diacetate With potassium permanganate; sodium perchlorate In dichloromethane; water for 0.05h; Stage #2: N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water at 20℃; for 6h; Stage #3: With acetic acid for 3h; Product distribution / selectivity; Heating / reflux; | 32% |
Stage #1: pseudodiosgenin diacetate With potassium permanganate; sodium iodate In dichloromethane; water for 0.05h; Stage #2: N-benzyl-N,N,N-triethylammonium chloride In dichloromethane; water at 20℃; for 10h; Stage #3: With acetic acid for 3h; Product distribution / selectivity; Heating / reflux; | 32% |
3',4',6'-tri-O-acetyl-1',2',O-(16-dehydropregnenolone-3-yloxyethylidene)-α-D-glucopyranose
A
16-dehydropregnenolone
B
16-dehydropregnenolone acetate
C
di-16-dehydropregnenolone-2-yl ether
D
3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-16-dehydropregnanolone
E
3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-16-dehydropregnenolone
Conditions | Yield |
---|---|
With mercury dibromide In nitromethane at 90℃; for 1h; Product distribution; other molar ratio, other time; | A 2% B 8% C 14% D 36.3% E 4% |
3',4',6'-tri-O-acetyl-1',2',O-(16-dehydropregnenolone-3-yloxyethylidene)-α-D-glucopyranose
A
16-dehydropregnenolone acetate
B
di-16-dehydropregnenolone-2-yl ether
C
3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-16-dehydropregnanolone
D
3-O-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-16-dehydropregnenolone
Conditions | Yield |
---|---|
With mercury dibromide In nitromethane at 90℃; for 1h; Further byproducts given; | A 8% B 14% C 36.3% D 4% |
(25R)-22,26-epiminocholesta-5,22(N)-diene-3β,16β-diol diacetate
A
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With manganese(IV) oxide In chloroform for 48h; Ambient temperature; | A 5% B 6% C 16% |
Conditions | Yield |
---|---|
With 2,4,6-trimethyl-pyridine |
Pregna-5,16-diene-20-yne-3β-ol 3-Acetate
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; acetic anhydride; mercury(II) oxide Reagens 4: Essigsaeure;und anschliessend mit Wasser; | |
With water; aniline; mercury(II) chloride Reagens 4: Benzol; |
Conditions | Yield |
---|---|
at 220℃; und anschliessend unter 10 Torr auf 300grad; |
Conditions | Yield |
---|---|
With pyridine |
acetic acid
(22R,25R)-28-acetyl-spirosol-5-en-3β-ol
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
anschliessendes Behandeln mit CrO3 in wss. Essigsaeure und Erhitzen der danach erhaltenen Reaktionsloesung auf Siedetemperatur; |
Conditions | Yield |
---|---|
anschliessendes Behandeln mit CrO3 in wss. Essigsaeure und Erhitzen der danach erhaltenen Reaktionsloesung auf Siedetemperatur; |
acetic anhydride
solasodine
A
3β-acetoxy-16α-methoxy-pregn-5-en-20-one
B
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
Behandeln mit CrO3 in wss. Essigsaeure, Erwaermen mit methanol. KOH und Behandeln mit Acetanhydrid und Pyridin; |
Acetic acid (3S,8R,9S,10R,13S,14S,16R,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-3-yl ester
A
3β-acetoxy-16α-hydroxy-pregn-5-en-20-one
B
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With chromium dichloride |
Conditions | Yield |
---|---|
With dmap In dichloromethane Heating; Yield given; |
16-dehydro-pregnenolone acetate ethylene ketal
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With aluminium(III) iodide In acetonitrile; benzene for 0.25h; Ambient temperature; | 85 % Chromat. |
Conditions | Yield |
---|---|
Yield given. Multistep reaction; | |
Multi-step reaction with 3 steps 1: 1 h / 195 °C 2: CrO3; AcOH / 3 h / 10 - 15 °C 3: 2.3 g / sodium bisulphite; AcOH / H2O / 1 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: boron trifluoride diethyl etherate / dichloromethane 2: acetic acid; chromium(VI) oxide / dichloromethane View Scheme |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethyl acetate at 30℃; under 2327.2 Torr; for 16h; | 98% |
With ammonium formate; palladium on activated charcoal In methanol for 0.6h; Heating; | 98% |
With hydrogen; palladium on activated charcoal In ethyl acetate at 30℃; under 2327.23 Torr; for 12h; | 98% |
16-dehydropregnenolone acetate
3β-hydroxypregn-5-en-20-one-3-acetate
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 30℃; for 6h; | 98.18% |
With magnesium; zinc(II) chloride for 0.583333h; | 90% |
With hydrogen; Cu/Al2O3 under 760 Torr; | 87% |
16-dehydropregnenolone acetate
3β-acetoxy-5α,6α-epoxypregn-16-ene-20-one
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 1h; | 98% |
With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 0.5h; | 97% |
With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 0.5h; | 97% |
With silica gel; 3-chloro-benzenecarboperoxoic acid at 20℃; for 1.5h; | 91.75% |
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃; |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol at 30℃; under 2844.39 Torr; for 12h; | 98% |
With 5% Pd(II)/C(eggshell); hydrogen In ethanol under 2327.23 Torr; for 10h; | 95% |
With 5%-palladium/activated carbon; hydrogen In ethanol under 2327.23 Torr; for 12h; | 95% |
Multi-step reaction with 2 steps 1: hydrogen; 5%-palladium/activated carbon / ethyl acetate / 20 °C / 750.08 Torr 2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 20 °C / 750.08 Torr View Scheme |
N-hydroxy-4-methylbenzenecarboximidoyl chloride
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
Stage #1: N-hydroxy-4-methylbenzenecarboximidoyl chloride; 16-dehydropregnenolone acetate With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 0.0833333h; Stage #2: In toluene at 111℃; for 2h; regioselective reaction; | 98% |
Conditions | Yield |
---|---|
With sodium hydroxide; urea hydrogen peroxide adduct In methanol; water at 5℃; for 72h; | 97% |
With sodium hydroxide; urea hydrogen peroxide adduct In methanol; water at 5 - 500℃; for 72h; | 97% |
With sodium hydroxide; dihydrogen peroxide In methanol; water at 5 - 15℃; for 23h; | 95% |
Conditions | Yield |
---|---|
With water; sodium hydroxide In methanol at 20℃; for 12h; Reagent/catalyst; Solvent; | 97% |
With potassium hydroxide; tert-butyl alcohol In water at 30℃; for 10h; | 96% |
With potassium hydroxide In tert-butyl alcohol at 30℃; for 10h; | 96% |
16-dehydropregnenolone acetate
3β-acetoxy-20-hydroxyiminopregna-5,16-diene
Conditions | Yield |
---|---|
With pyridine; hydroxylamine hydrochloride In ethanol for 0.5h; Reflux; | 97% |
With pyridine; hydroxylamine hydrochloride In ethanol for 0.5h; Reflux; | 97% |
With pyridine; hydroxylamine hydrochloride for 96h; Cooling; | 96% |
16-dehydropregnenolone acetate
N-hydroxy-4-methoxy-benzenecarboximidoyl chloride
Conditions | Yield |
---|---|
Stage #1: 16-dehydropregnenolone acetate; N-hydroxy-4-methoxy-benzenecarboximidoyl chloride With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 0.0833333h; Stage #2: In toluene at 111℃; for 2h; regioselective reaction; | 97% |
16-dehydropregnenolone acetate
(3β)-21-bromo-20-oxopregna-5,16-dien-3-yl acetate
Conditions | Yield |
---|---|
With t-butyldimethylsiyl triflate; bromine; triethylamine In dichloromethane | 95% |
With copper(ll) bromide In i-Amyl alcohol at 46 - 48℃; | 95% |
With copper(ll) bromide In tetrahydrofuran |
t-butyldimethylsiyl triflate
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 0 - 20℃; for 0.75h; | 95% |
With triethylamine In dichloromethane at 5℃; | 82% |
acetyl hydrazine hydrochloride
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With iodine In ethanol for 1h; Cycloaddition; Heating; | 95% |
methylmagnesium bromide
16-dehydropregnenolone acetate
16α-methylpregn-5-en-3β-ol-20-one 3-acetate
Conditions | Yield |
---|---|
Stage #1: methylmagnesium bromide; 16-dehydropregnenolone acetate With copper(l) chloride In tetrahydrofuran at -10 - 0℃; for 0.333333h; Grignard reaction; Inert atmosphere; Stage #2: With methanol In tetrahydrofuran at -5℃; for 0.25h; Stage #3: With water In tetrahydrofuran; methanol at 5 - 10℃; for 2h; | 95% |
4-fluorophenyl benzaldehyde-tosylhydrazone sodium salt
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
In methanol; dichloromethane at 175℃; under 0.05 Torr; | 95% |
sodium 2-benzylidene-1-tosylhydrazin-1-ide
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
In methanol; dichloromethane at 175℃; under 0.05 Torr; | 95% |
16-dehydropregnenolone acetate
benzohydroximoyl chloride
3β-acetoxy-3'-phenyl-2'-isoxazolino[4',5'-d:16α,17α]pregn-5-en-20-one
Conditions | Yield |
---|---|
Stage #1: 16-dehydropregnenolone acetate; benzohydroximoyl chloride With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 0.0833333h; Stage #2: In toluene at 111℃; for 2h; regioselective reaction; | 95% |
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With hydrogenchloride In methanol | 94% |
16-dehydropregnenolone acetate
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In chloroform for 3h; Reflux; | 93.54% |
Conditions | Yield |
---|---|
Stage #1: 16-dehydropregnenolone acetate With hydrogen at 0 - 25℃; for 1h; Stage #2: With potassium hydroxide for 2h; Reflux; | 92.8% |
Multi-step reaction with 2 steps 1: 98 percent / H2 / Pd/C / ethyl acetate / 12 h / 30 °C / 2327.23 Torr 2: 97 percent / potassium hydroxide; H2O / methanol / 2 h / 30 °C View Scheme | |
Multi-step reaction with 2 steps 1: 97 percent / H2 / Pd/C / 15 h / 30 °C / 2327.17 Torr 2: 96 percent / KOH / 2-methyl-propan-2-ol; H2O / 16 h / 30 °C View Scheme |
Conditions | Yield |
---|---|
With iodine for 2h; Heating; | 91.7% |
Conditions | Yield |
---|---|
With lithium ethoxide In tetrahydrofuran at 20℃; | 91% |
Conditions | Yield |
---|---|
With pyridine; sodium methylate; sodium chloride for 1h; | 91% |
nitromethane
16-dehydropregnenolone acetate
3β-acetoxy-16α-nitromethyl-5-pregnan-20-one
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 12h; | 90% |
With piperidine | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; Michael condensation; | |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane |
16-dehydropregnenolone acetate
allyl-trimethyl-silane
3β-acetoxy-16α-prop-2'-enylpregn-5-en-20-one
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane for 5h; Ambient temperature; | 90% |
phenylhydrazine hydrochloride
16-dehydropregnenolone acetate
3-acetoxy-5'-methyl-2'-phenyl-2'H-androst-5-eno[16,17-c]pyrazole
Conditions | Yield |
---|---|
With iodine In ethanol for 1h; Cycloaddition; Heating; | 88% |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 15 - 20℃; for 0.5h; Michael addition; | 88% |
methylmagnesium bromide
16-dehydropregnenolone acetate
17α-hydroperoxy-16α-methyl-20-oxopregn-5-en-3β-yl acetate
Conditions | Yield |
---|---|
With copper(l) chloride In tetrahydrofuran; benzene at 0 - 5℃; for 0.333333h; Grignard reaction; Inert atmosphere; | 88% |
16-dehydropregnenolone acetate
3β-acetoxy-5α,6β-dichloropregn-16-en-20-one
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; tetradecyltrimethylammonium permanganate In dichloromethane at 0 - 3℃; for 1.5h; | 87% |
Molecular Structure of 16-Dehydropregnenolone acetate (CAS NO.979-02-2):
IUPAC Name: [(3S,8R,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Empirical Formula: C23H32O3
Molecular Weight: 356.4984
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 43.37 Å2
Index of Refraction: 1.546
Molar Refractivity: 101.63 cm3
Molar Volume: 320.5 cm3
Surface Tension: 42 dyne/cm
Density: 1.11 g/cm3
Flash Point: 200.1 °C
Enthalpy of Vaporization: 72.58 kJ/mol
Boiling Point: 464.4 °C at 760 mmHg
Vapour Pressure: 8.38E-09 mmHg at 25°C
Melting point: 170-178°C
InChI
InChI=1/C23H32O3/c1-14(24)19-7-8-20-18-6-5-16-13-17(26-15(2)25)9-11-22(16,3)21(18)10-12-23(19,20)4/h5,7,17-18,20-21H,6,8-13H2,1-4H3/t17-,18-,20-,21-,22-,23+/m0/s1
Smiles
O=C(C)C1=CC[C@@H]2[C@@]1(CC[C@@H]1[C@@]3(CC[C@H](OC(=O)C)CC3=CC[C@@H]21)C)C
EINECS: 213-558-7
Product Categories: Steroids
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | > 8gm/kg (8000mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(2), Pg. 32, 1974. | |
mouse | LD50 | oral | > 8gm/kg (8000mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(2), Pg. 32, 1974. |
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
RTECS: TU4156200
16-Dehydropregnenolone acetate , with CAS number of 979-02-2, can be called Pregna-5,16-dien-20-one, 3-beta-hydroxy-, acetate ; Dehydropregnenolone acetate ; 3beta-Acetoxypregna-5,16-dien-20-one ; 20-Oxopregna-5,16-dien-3beta-yl acetate ; 16-Dehydropregnenolone acetate ; 16,17-Didehydropregnenolone acetate ; (3-beta)-3-(Acetyloxy)pregna-5,16-dien-20-one .
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