Product Name

  • Name

    Estradiene dione-3-keta

  • EINECS 427-230-8
  • CAS No. 5571-36-8
  • Article Data2
  • CAS DataBase
  • Density 1.2 g/cm3
  • Solubility 903μg/L at 25℃
  • Melting Point 152-154 °C
  • Formula C20H26O3
  • Boiling Point 488.1 °C at 760 mmHg
  • Molecular Weight 314.425
  • Flash Point 241.2 °C
  • Transport Information
  • Appearance off-white solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 5571-36-8 (Estradiene dione-3-keta)
  • Hazard Symbols
  • Synonyms Estra-5(10),9(11)-diene-3,17-dione,cyclic 3-(ethylene acetal) (7CI,8CI);Spiro[3H-cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolane],estra-5(10),9(11)-diene-3,17-dione deriv.;3,3-(Ethylenedioxy)estra-5(10),9(11)-dien-17-one;Estra-5(10),9(11)-diene-3,17-dione,cyclic 3-(1,2-ethanediyl acetal);
  • PSA 35.53000
  • LogP 3.93550

Synthetic route

(8S,13S,14S,17S)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol
53303-91-6

(8S,13S,14S,17S)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol

ethylene deltenone
5571-36-8

ethylene deltenone

Conditions
ConditionsYield
With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In dichloromethane for 0.25h; Ambient temperature;99.3%
ethylene glycol
107-21-1

ethylene glycol

17-hydroxy-estra-4,9-dien-3-one

17-hydroxy-estra-4,9-dien-3-one

ethylene deltenone
5571-36-8

ethylene deltenone

Conditions
ConditionsYield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester; pyridinium chlorochromate 2.) CH2Cl2; Yield given. Multistep reaction;
4,9-Androstadiene-3,17-dione
5173-46-6

4,9-Androstadiene-3,17-dione

ethylene deltenone
5571-36-8

ethylene deltenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaBH4 / tetrahydrofuran; methanol / -10 °C
2: 1.) (EtO)3CH, pTsOH, 2.) pyridinium chlorochromate / 2.) CH2Cl2
View Scheme
17β-hydroxyestra-4,9-dien-3-one
6218-29-7

17β-hydroxyestra-4,9-dien-3-one

ethylene deltenone
5571-36-8

ethylene deltenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / H2SO4 / benzene; CH2Cl2 / 2.5 h / Heating
2: 99.3 percent / N-methylmorpholine N-oxide, (nC3H7)4NRuO4 / CH2Cl2 / 0.25 h / Ambient temperature
View Scheme
ethylene deltenone
5571-36-8

ethylene deltenone

(8S,13S,14S,17S)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol
53303-91-6

(8S,13S,14S,17S)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 25℃; for 1.5h; Inert atmosphere;100%
With sodium tetrahydroborate In methanol for 0.25h; Ambient temperature;98%
With sodium hydroxide; sodium tetrahydroborate In methanol; water at 2℃; for 2.08333h;
With potassium borohydride; butan-1-ol at 30℃; Reagent/catalyst; Temperature;9.3 g
With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 20℃; for 1.5h;
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

ethylene deltenone
5571-36-8

ethylene deltenone

17-[[(trifluoromethyl)sulfonyl]oxy]estra-5(10),9(11),16-trien-3-one cyclic 1,2-ethanediyl acetal
866004-28-6

17-[[(trifluoromethyl)sulfonyl]oxy]estra-5(10),9(11),16-trien-3-one cyclic 1,2-ethanediyl acetal

Conditions
ConditionsYield
Stage #1: ethylene deltenone With lithium hexamethyldisilazane In tetrahydrofuran at -15℃; for 0.5h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at 0℃; for 3h; Further stages.;		100%
Stage #1: ethylene deltenone With lithium hexamethyldisilazane In tetrahydrofuran at -40 - -15℃; for 0.5h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -15 - 0℃; for 3h;
Stage #3: With sodium hydrogencarbonate In tetrahydrofuran; water		100%
sodium acetylide

sodium acetylide

ethylene deltenone
5571-36-8

ethylene deltenone

(8S,13S,14S,17R)-17-ethynyl-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol
5490-76-6

(8S,13S,14S,17R)-17-ethynyl-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;100%
ethylene deltenone
5571-36-8

ethylene deltenone

(8S,13S,14S)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3] dioxolan]-17-ol

(8S,13S,14S)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3] dioxolan]-17-ol

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate at 20℃;100%
With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 1.5h;100%
With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 1.5h;
sodium acetylide
1066-26-8

sodium acetylide

ethylene deltenone
5571-36-8

ethylene deltenone

(8S,13S,14S,17R)-17-ethynyl-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol
5490-76-6

(8S,13S,14S,17R)-17-ethynyl-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol

Conditions
ConditionsYield
In tetrahydrofuran at -2 - 0℃; for 6.5h; Inert atmosphere; Industrial scale;99%
In tetrahydrofuran at -2 - 0℃; for 6h; Inert atmosphere; Large scale;99%
In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;95%
Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

ethylene deltenone
5571-36-8

ethylene deltenone

3,3-ethylenedioxy-17β-hydroxy-17-(1,1,2,2,2-pentafluoroethyl)-estra-5(10),9(11)-diene
1421036-65-8

3,3-ethylenedioxy-17β-hydroxy-17-(1,1,2,2,2-pentafluoroethyl)-estra-5(10),9(11)-diene

Conditions
ConditionsYield
Stage #1: Pentafluoroethyl iodide; ethylene deltenone In toluene at -78℃; for 0.166667h;
Stage #2: With methyllithium lithium bromide In diethyl ether; toluene at -78 - 0℃; for 2.08333h;		85%
diethyl cyanophosphonate
2942-58-7

diethyl cyanophosphonate

ethylene deltenone
5571-36-8

ethylene deltenone

17-cyano-3,3-[1,2-ethanediylbis(oxy)]estra-5(10),9(11)-diene
240806-36-4

17-cyano-3,3-[1,2-ethanediylbis(oxy)]estra-5(10),9(11)-diene

Conditions
ConditionsYield
Stage #1: diethyl cyanophosphonate; ethylene deltenone With lithium cyanide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: With samarium diiodide In tetrahydrofuran; tert-butyl alcohol for 3.5h; Further stages.;		79%
Stage #1: diethyl cyanophosphonate; ethylene deltenone With lithium cyanide In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: With samarium diiodide; tert-butyl alcohol In tetrahydrofuran Inert atmosphere;		79%
ethylene deltenone
5571-36-8

ethylene deltenone

(5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one
39931-88-9, 116003-08-8, 39931-87-8

(5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexachloro-propan-2-one; dihydrogen peroxide In dichloromethane for 72h;76.1%
With disodium hydrogenphosphate; dihydrogen peroxide; Hexafluoroacetone In dichloromethane at 0 - 4℃; for 18h;59.76%
With disodium hydrogenphosphate; dihydrogen peroxide; Hexafluoroacetone In dichloromethane at 0 - 20℃; for 18h;53%
ethylene deltenone
5571-36-8

ethylene deltenone

3-(ethylenedioxy)estra-5,10-epoxy-9(11)-ene-17-one
786698-67-7

3-(ethylenedioxy)estra-5,10-epoxy-9(11)-ene-17-one

Conditions
ConditionsYield
With pyridine; dihydrogen peroxide; Hexafluoroacetone In dichloromethane at 20℃; for 16h;74%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

ethylene deltenone
5571-36-8

ethylene deltenone

(8S,13S,14S,17S)-17-(3,3-dimethylbut-1-yn-1-yl)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol

(8S,13S,14S,17S)-17-(3,3-dimethylbut-1-yn-1-yl)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol

Conditions
ConditionsYield
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 0.416667h;
Stage #2: ethylene deltenone In tetrahydrofuran at -78 - 20℃; for 0.95h;		74%
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.416667h; Inert atmosphere;
Stage #2: ethylene deltenone In tetrahydrofuran; hexane at -78 - 25℃; for 0.95h; Inert atmosphere;		74%
1,1-dibromo-3-methyl-1-butene
32363-92-1

1,1-dibromo-3-methyl-1-butene

ethylene deltenone
5571-36-8

ethylene deltenone

estra-5(10),9(11)-dien-3-one, 17β-hydroxy-17α-(3-methyl-1-butynyl) cyclic 3-(1,2-ethanediyl acetal)
264129-99-9

estra-5(10),9(11)-dien-3-one, 17β-hydroxy-17α-(3-methyl-1-butynyl) cyclic 3-(1,2-ethanediyl acetal)

Conditions
ConditionsYield
Stage #1: 1,1-dibromo-3-methyl-1-butene With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 2h; Metallation;
Stage #2: ethylene deltenone In tetrahydrofuran; hexane at 25℃; for 8h; Alkynylation;		71%
[(p-methylphenyl)sulfonylmethyl]isonitrile
38622-91-2, 36635-61-7

[(p-methylphenyl)sulfonylmethyl]isonitrile

ethylene deltenone
5571-36-8

ethylene deltenone

17-cyano-3,3-[1,2-ethanediylbis(oxy)]estra-5(10),9(11)-diene
240806-36-4

17-cyano-3,3-[1,2-ethanediylbis(oxy)]estra-5(10),9(11)-diene

Conditions
ConditionsYield
With potassium tert-butylate In 1,2-dimethoxyethane; tert-butyl alcohol for 2.5h;71%
ethylene deltenone
5571-36-8

ethylene deltenone

A

(5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one
39931-88-9, 116003-08-8, 39931-87-8

(5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one

B

3,3-(ethylenedioxy)-5β,10β-epoxyestra-9(11)-ene-17-one
39931-88-9

3,3-(ethylenedioxy)-5β,10β-epoxyestra-9(11)-ene-17-one

Conditions
ConditionsYield
With pyridine; dihydrogen peroxide In dichloromethane at 0℃; for 18h; Inert atmosphere;A 68%
B 13%
With pyridine; dihydrogen peroxide; Hexafluoroacetone In dichloromethane at 0 - 20℃; for 18h; optical yield given as %de;A 56%
B 18%
With pyridine; dihydrogen peroxide; Hexafluoroacetone In dichloromethane at 0℃; for 18h; Inert atmosphere;A 56%
B 18%
N-[(trifluoromethyl)sulfanyl]aniline
1045821-71-3

N-[(trifluoromethyl)sulfanyl]aniline

ethylene deltenone
5571-36-8

ethylene deltenone

cyclic-3-(1,2-ethanediylacetal)-estra-5(10),9(11)-dien-16,16-bis((trifluoromethyl)thio)-3,17-dione

cyclic-3-(1,2-ethanediylacetal)-estra-5(10),9(11)-dien-16,16-bis((trifluoromethyl)thio)-3,17-dione

Conditions
ConditionsYield
With acetyl chloride In 1-methyl-pyrrolidin-2-one at 20℃; for 15h; Inert atmosphere;65%
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

ethylene deltenone
5571-36-8

ethylene deltenone

(8S,13S,14S)-13-methyl-17-methylene-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolane]

(8S,13S,14S)-13-methyl-17-methylene-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolane]

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: ethylene deltenone In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;		65%
ethylene deltenone
5571-36-8

ethylene deltenone

(8S,13S,14S)-16-bromo-13-methyl-1,4,6,7,8,12,13,14,15,16-decahydrospiro[cyclopenta [a]phenanthrene-3,2'-[1,3]dioxolan]-17(2H)-one

(8S,13S,14S)-16-bromo-13-methyl-1,4,6,7,8,12,13,14,15,16-decahydrospiro[cyclopenta [a]phenanthrene-3,2'-[1,3]dioxolan]-17(2H)-one

Conditions
ConditionsYield
Stage #1: ethylene deltenone With chloro-trimethyl-silane; lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 1.5h; Inert atmosphere; Sealed tube;
Stage #2: With N-Bromosuccinimide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Sealed tube;		64%
1,1,1,3,3,3-hexafluoro-2-propanone trihydrate

1,1,1,3,3,3-hexafluoro-2-propanone trihydrate

aqueous Na2 S2 O3

aqueous Na2 S2 O3

Na2 HPO4

Na2 HPO4

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

ethylene deltenone
5571-36-8

ethylene deltenone

A

3,3-[1,2-Ethanediylbis(oxy)]-5α,10α-(oxido)estr-9(11)-en-17-one

3,3-[1,2-Ethanediylbis(oxy)]-5α,10α-(oxido)estr-9(11)-en-17-one

B

11β-[4-(N,N-Dimethylamino)phenyl]-17β-nitroestra-4,9-dien-3-one
244304-80-1

11β-[4-(N,N-Dimethylamino)phenyl]-17β-nitroestra-4,9-dien-3-one

Conditions
ConditionsYield
In diethyl ether; dichloromethane; ethyl acetateA 53%
B n/a
...Expand
methylenedimethyl sulfurane
6814-64-8, 40651-06-7

methylenedimethyl sulfurane

ethylene deltenone
5571-36-8

ethylene deltenone

spiro-2'-(1'-oxacyclopropane)-17(S)-<3,3-(ethylenedioxy)-5(10),9(11)-estradiene>
67308-78-5

spiro-2'-(1'-oxacyclopropane)-17(S)-<3,3-(ethylenedioxy)-5(10),9(11)-estradiene>

Conditions
ConditionsYield
In tetrahydrofuran; dimethyl sulfoxide38.8%
ethylene deltenone
5571-36-8

ethylene deltenone

acetylene
74-86-2

acetylene

(8S,13S,14S,17R)-17-ethynyl-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol
5490-76-6

(8S,13S,14S,17R)-17-ethynyl-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran
Stage #1: acetylene With potassium tert-butylate In tetrahydrofuran at -5 - 5℃; for 1h;
Stage #2: ethylene deltenone In tetrahydrofuran for 1h;

Estradiene dione-3-keta Specification

Estradiene dione-3-keta(CAS NO.5571-36-8), its Synonyms are Cyclic-3-(1,2-ethanediyl acetal)-estra-5(10),9(11)-dien-3,17-dione; 3-Ethylenedioxy-estra-5(10),9(11)-diene-17-one; Estradiene. It is off-white solid. Estradiene dione-3-keta is used as mifepristone intermediate; antiprogestational antiglucocorticoid antagonist steroidal spirooxazole.

Physical properties about Estradiene dione-3-keta are: (1)ACD/LogP: 1.717; (2)ACD/LogD (pH 5.5): 1.72; (3)ACD/LogD (pH 7.4): 1.72; (4)ACD/BCF (pH 5.5): 11.88; (5)ACD/BCF (pH 7.4): 11.88; (6)ACD/KOC (pH 5.5): 204.68; (7)ACD/KOC (pH 7.4): 204.68; (8)#H bond acceptors: 3; (9)Index of Refraction: 1.582 ; (10)Molar Refractivity: 87.151 cm3; (11)Molar Volume: 261.018 cm3; (12)Polarizability: 34.549 10-24cm3; (13)Surface Tension: 46.6419982910156 dyne/cm ; (14)Density: 1.205 g/cm3; (15)Flash Point: 241.25 °C; (16)Enthalpy of Vaporization: 75.417 kJ/mol; (17)Boiling Point: 488.126 °C at 760 mmHg

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