Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; N-hydroxyphthalimide; cobalt(II) acetate In acetone at 20℃; for 5h; regioselective reaction; | 81.1% |
With N-hydroxyphthalimide; sodium dichromate; chromium(III) perchlorate In acetone at 20℃; for 48h; Product distribution / selectivity; | 74.25% |
With tert.-butylhydroperoxide; dirhodium(II) tetrakis(caprolactam) In water; 1,2-dichloro-ethane at 40℃; for 20h; | 74% |
(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,3,4,8,9,10,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-7(2H)-one
5-androstene-3β-ol-7,17-dione
Conditions | Yield |
---|---|
With perchloric acid; water In acetone at 20℃; for 20h; | 65% |
dehydroepiandrosterone
A
5-androstene-3β-ol-7,17-dione
B
3β,7α-dihydroxyandrost-5-ene-17-one
C
5-androsten-3β,7β-diol-17-one
Conditions | Yield |
---|---|
With Mortierella isabellina AM212 fungal strain for 12h; Enzymatic reaction; | A 6% B 53.5% C 24% |
With Absidia coerulea AM93 In acetone at 20℃; for 8h; Time; Enzymatic reaction; | A 5.5% B 22% C 49% |
3β-hydroxy-17,17-ethylenedioxo-5-androstene
5-androstene-3β-ol-7,17-dione
Conditions | Yield |
---|---|
With CrO3/NHPI on activated clay In dichloromethane at 20℃; | 40% |
prasterone acetate
A
5-androstene-3β-ol-7,17-dione
B
3β,7α-dihydroxyandrost-5-ene-17-one
C
5-androsten-3β,7β-diol-17-one
D
3β,14α-dihydroxyandrost-5-en-7,17-dione
Conditions | Yield |
---|---|
With Cunninghamella elegans In ethanol for 72h; Further byproducts given; | A 5.4% B 26.8% C 9% D 1.1% |
With Cunninghamella elegans In ethanol for 72h; Further byproducts given; | A 5.4% B 26.8% C 9% D 1.1% |
dehydroepiandrosterone
A
5-androstene-3β-ol-7,17-dione
B
3β,7α-dihydroxyandrost-5-ene-17-one
C
5-androsten-3β,7β-diol-17-one
Conditions | Yield |
---|---|
With Ulocladium chartarum MRC 72584 In water; N,N-dimethyl-formamide at 28℃; for 120h; Enzymatic reaction; | A 6% B 12% C 16% D 3% E 4% F 2% G 3% |
prasterone acetate
A
5-androstene-3β-ol-7,17-dione
B
5-androsten-3β,7β-diol-17-one
C
5,6β-epoxy-3β,12α-dihydroxy-5β-androstan-17-one
D
3β,14α-dihydroxyandrost-5-en-7,17-dione
Conditions | Yield |
---|---|
With Cunninghamella elegans In ethanol for 72h; Further byproducts given; | A 5.4% B 9% C 4.1% D 1.1% |
Conditions | Yield |
---|---|
und anschliessend Hydrolysieren; |
Conditions | Yield |
---|---|
With chromium(VI) oxide und anschliessend Hydrolysieren; |
Conditions | Yield |
---|---|
With sodium carbonate In methanol | |
With sodium hydrogencarbonate In methanol | 307 mg |
dehydroepiandrosterone
A
5-androstene-3β-ol-7,17-dione
B
3β,7α-dihydroxyandrost-5-ene-17-one
C
Androst-5-ene-3beta,7alpha,17beta-triol
Conditions | Yield |
---|---|
With fungus Fusarium oxysporum var. cubense In ethanol at 27℃; Product distribution; biotransformation; Microbiological reaction; fungus Fusarium oxysporum var. cubense (from rhizome of banana plant showing symptoms of Panama disease); | |
With fungus Fusarium oxysporum In ethanol at 27℃; for 180h; biotransformation; Title compound not separated from byproducts; |
5-androstene-3β-ol-7,17-dione
Conditions | Yield |
---|---|
With perchloric acid In ethyl acetate at 25℃; for 0.25h; | 99.5 % Chromat. |
5-androsten-7,17-dione-3β-ol ethylene ketal tert-butyldimethylsilyl ether
5-androstene-3β-ol-7,17-dione
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; methanol |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / N-hydroxyphthalimide, azobis(cyclohexane-carbonitrile), air / acetone; ethyl acetate / 9 h / Heating 2: Na2CO3 / methanol View Scheme |
3β,7α-dihydroxyandrost-5-ene-17-one
5-androstene-3β-ol-7,17-dione
Conditions | Yield |
---|---|
With polyoxyethylenesorbitan monooleate; soy protein, hydrolyzed; dipotassium hydrogenphosphate; potassium dihydrogenphosphate; yiest; autolysed extract of In water for 144h; Enzymatic reaction; | |
With Mortierella isabellina AM212 fungal strain for 12h; Enzymatic reaction; | 9.7 %Chromat. |
Conditions | Yield |
---|---|
With Mortierella isabellina AM212 fungal strain for 12h; Enzymatic reaction; | 32 %Chromat. |
5-androstene-3β-ol-7,17-dione
acetic anhydride
3-O-acetyl-7-oxo-dehydroepiandrosterone
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 0.0333333h; microwave irradiation; | 96% |
for 3h; Reflux; | 85% |
5-androstene-3β-ol-7,17-dione
tert-butyldimethylsilyl chloride
(3β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]androst-5-ene-7,17-dione
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h; | 92.6% |
With 1H-imidazole |
Conditions | Yield |
---|---|
In N-methyl-acetamide | 92.6% |
Conditions | Yield |
---|---|
In pyridine at 0 - 5℃; | 90% |
Conditions | Yield |
---|---|
In pyridine | 90% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; cerium(III) chloride In methanol; dichloromethane at 0 - 5℃; for 0.5h; pH=15; | 88% |
Conditions | Yield |
---|---|
With perchloric acid In methanol; water at 20℃; for 12h; | 80% |
5-androstene-3β-ol-7,17-dione
androst-5-en-7,17-dione-3β-yl 2-[4-N,N-bis(2-chloroethyl)amino-phenyl]butanoate
Conditions | Yield |
---|---|
With dmap In toluene for 1.5h; Inert atmosphere; Reflux; | 80% |
Conditions | Yield |
---|---|
In pyridine at 0 - 5℃; | 78% |
5-androstene-3β-ol-7,17-dione
Conditions | Yield |
---|---|
With potassium permanganate; sodium periodate; potassium carbonate In water; tert-butyl alcohol at 60℃; for 2.33333h; | 78% |
Conditions | Yield |
---|---|
In tetrahydrofuran-pyridine | 78% |
Conditions | Yield |
---|---|
In pyridine | 78% |
3,4-dihydro-2H-pyran
5-androstene-3β-ol-7,17-dione
A
3β-(2-tetrahydropyranyloxy)-androst-5-ene-7,17-dione
B
androsta-3,5-diene-7,17-dione
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 3h; | A 68% B 0.150 g |
Conditions | Yield |
---|---|
In pyridine at 0 - 5℃; | 65% |
octyl chloroformate
5-androstene-3β-ol-7,17-dione
3β-carbooctyloxyandrost-5-ene-7,17-dione
Conditions | Yield |
---|---|
In pyridine | 65% |
5-androstene-3β-ol-7,17-dione
(fluorenylmethoxy)carbonyl chloride
Conditions | Yield |
---|---|
In pyridine at 20℃; for 1h; | 57% |
5-androstene-3β-ol-7,17-dione
Conditions | Yield |
---|---|
With cyclohexanone; aluminum isopropoxide; toluene |
5-androstene-3β-ol-7,17-dione
p-toluenesulfonyl chloride
3β-Tosyloxy-androsten-(5)-dion-(7,17)
Conditions | Yield |
---|---|
With pyridine |
diazomethane
5-androstene-3β-ol-7,17-dione
Conditions | Yield |
---|---|
(i) aq. H2O2, KOH, MeOH, (ii) /BRN= 102415/; Multistep reaction; |
Conditions | Yield |
---|---|
With pyridine |
Conditions | Yield |
---|---|
With pyridine |
7-Keto-dehydroepiandrosterone has the IUPAC Name of (3S,8R,9S,10R,13S,14S)-3-Hydroxy-10,13-dimethyl-2,3,4,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-7,17-dione. With the CAS NO.566-19-8, it is also called 7-Keto DHEA; 7-Oxo-DHEA; DHEA, 7-keto-; UNII-2334LJD2E9; 3beta-Hydroxyandrost-5-ene-7,17-dione. 7-Oxodehydroepiandrosterone (CAS NO.566-19-8) is used as a pharmaceutical intermediates.
Physical properties about 7-Keto-dehydroepiandrosterone are: (1)ACD/LogP: 1.669; (2)ACD/LogD (pH 5.5): 1.67; (3)ACD/LogD (pH 7.4): 1.67; (4)ACD/BCF (pH 5.5): 10.93 ; (5)ACD/BCF (pH 7.4): 10.93; (6)ACD/KOC (pH 5.5): 192.76; (7)ACD/KOC (pH 7.4): 192.76; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.569; (12)Molar Refractivity: 83.229 cm3; (13)Molar Volume: 253.886 cm3; (14)Polarizability: 32.995 10-24cm3; (15)Surface Tension: 48.1559982299805 dyne/cm; (16)Density: 1.191 g/cm3; (17)Flash Point: 256.478 °C; (18)Enthalpy of Vaporization: 85.408 kJ/mol; (19)Boiling Point: 477.144 °C at 760 mmHg
You can still convert the following datas into molecular structure:
(1)InChI=1S/C19H26O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-14,17,20H,3-9H2,1-2H3/t12-,13-,14-,17-,18-,19-/m0/s1;
(2)InChIKey=KPRGOTLNGIBVFL-GINZOMEDSA-N;
(3)SmilesC1[C@@H](CC2=CC([C@H]3[C@@H]4CCC([C@@]4(C)CC[C@H]3[C@@]2(C1)C)=O)=O)O;
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