Product Name

  • Name

    Ethylmetrienone

  • EINECS
  • CAS No. 848-04-4
  • Article Data25
  • CAS DataBase
  • Density 1.084 g/cm3
  • Solubility
  • Melting Point
  • Formula C20H26O2
  • Boiling Point 439.883 °C at 760 mmHg
  • Molecular Weight 298.425
  • Flash Point 185.526 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 848-04-4 (Ethylmetrienone)
  • Hazard Symbols
  • Synonyms 18-Methylestronemethyl ether;
  • PSA 26.30000
  • LogP 4.51050

Synthetic route

(+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene
3625-82-9

(+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane for 0.5h; Ambient temperature;97%
With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide In dichloromethane for 0.5h;95%
With chromium(VI) oxide; sulfuric acid In acetone
jones reagent

jones reagent

(+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene
3625-82-9

(+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
In water; isopropyl alcohol; acetone
levonorgestrel
797-63-7

levonorgestrel

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / Ag2CO3, Celite / toluene / Heating
2: (NH4)2Ce(NO3)6, I2 / 2.5 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 98 percent / Ag2CO3, Celite / toluene / Heating
2: 1) (NH4)2Ce(NO3)6, I2, 2) H2 / 2) 5percent Pd/CaCO3 / 1) reflux, 2.5 h, 2) ethyl acetate, 40 psi, overnight
View Scheme
Multi-step reaction with 4 steps
1: 98 percent / Ag2CO3, Celite / toluene / Heating
3: 85 percent / 1 N aq. KOH / tetrahydrofuran; methanol / 1 h / Ambient temperature
4: 97 percent / N-methylmorpholine N-oxide, tetrapropylammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
13β-ethyl-3-hydroxygona-1,3,5(10)-trien-17-one
6544-68-9

13β-ethyl-3-hydroxygona-1,3,5(10)-trien-17-one

dimethyl sulfate
77-78-1

dimethyl sulfate

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
In acetone Reflux;29 g
2-ethyl-1,3-cyclopentanedione
823-36-9

2-ethyl-1,3-cyclopentanedione

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: triethylenediamine / xylene
2: aq. HCl / methanol
3: NaBH4 / methanol
4: H2 / Raney-Ni / dioxane
5: Py
6: KOH / methanol
7: Li, liq. NH3 / diethyl ether; dioxane
8: CrO3, aq. H2SO4 / acetone
View Scheme
(+/-)-13-ethyl-3-methoxygona-1,3,5(10),8,14-pentaen-17-one
848-07-7

(+/-)-13-ethyl-3-methoxygona-1,3,5(10),8,14-pentaen-17-one

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: NaBH4 / methanol
2: H2 / Raney-Ni / dioxane
3: Py
4: KOH / methanol
5: Li, liq. NH3 / diethyl ether; dioxane
6: CrO3, aq. H2SO4 / acetone
View Scheme
2-[2-(3,4-dihydro-6-methoxy-1(2H)-naphthalenylidene)ethyl]-2-ethyl-1,3-cyclopentanedione
850-92-0

2-[2-(3,4-dihydro-6-methoxy-1(2H)-naphthalenylidene)ethyl]-2-ethyl-1,3-cyclopentanedione

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: aq. HCl / methanol
2: NaBH4 / methanol
3: H2 / Raney-Ni / dioxane
4: Py
5: KOH / methanol
6: Li, liq. NH3 / diethyl ether; dioxane
7: CrO3, aq. H2SO4 / acetone
View Scheme
dl-3-Methoxy-13β-ethyl-gona-1,3,5(10),8,14-pentaen-17β-ol
2911-80-0, 14507-45-0, 15419-27-9, 24508-13-2

dl-3-Methoxy-13β-ethyl-gona-1,3,5(10),8,14-pentaen-17β-ol

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: H2 / Raney-Ni / dioxane
2: Py
3: KOH / methanol
4: Li, liq. NH3 / diethyl ether; dioxane
5: CrO3, aq. H2SO4 / acetone
View Scheme
13β-ethyl-gon-4-en-3,17-dione
21800-83-9

13β-ethyl-gon-4-en-3,17-dione

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: 85 percent / 1 N aq. KOH / tetrahydrofuran; methanol / 1 h / Ambient temperature
3: 97 percent / N-methylmorpholine N-oxide, tetrapropylammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: lithium bromide; copper(I) bromide / acetonitrile / 17 h / 5 - 25 °C / Inert atmosphere
2: acetone / Reflux
View Scheme
18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol
7443-72-3

18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Li, liq. NH3, PhNH2 / tetrahydrofuran
2: CrO3, aq. H2SO4 / acetone
View Scheme
Multi-step reaction with 2 steps
1: Li, liq. NH3 / diethyl ether; dioxane
2: CrO3, aq. H2SO4 / acetone
View Scheme
methanol
67-56-1

methanol

13β-ethyl-gon-4-en-3,17-dione
21800-83-9

13β-ethyl-gon-4-en-3,17-dione

A

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

B

D-(+)-13β-ethyl-3-methoxygona-1,3,5(10)-triene-6,17-dione

D-(+)-13β-ethyl-3-methoxygona-1,3,5(10)-triene-6,17-dione

Conditions
ConditionsYield
With copper(ll) bromide for 1h; Heating;A 12%
B 17.56%
With ammonium cerium(IV) nitrate; hydrogen; iodine; Lindlar's catalyst 1) reflux, 2.5 h, 2) ethyl acetate, 40 psi, overnight; Yield given. Multistep reaction. Yields of byproduct given;
...Expand
D-(+)-13β-ethyl-3-methoxygona-1,3,5(10)-trien-17β-yl trifluoroacetate
162210-67-5

D-(+)-13β-ethyl-3-methoxygona-1,3,5(10)-trien-17β-yl trifluoroacetate

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / 1 N aq. KOH / tetrahydrofuran; methanol / 1 h / Ambient temperature
2: 97 percent / N-methylmorpholine N-oxide, tetrapropylammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
l-3-Methoxy-13β-ethyl-gona-1,3,5(10),8-tetraen-17β-ol-hydrogensuccinat
10051-99-7

l-3-Methoxy-13β-ethyl-gona-1,3,5(10),8-tetraen-17β-ol-hydrogensuccinat

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: KOH / methanol
2: Li, liq. NH3 / diethyl ether; dioxane
3: CrO3, aq. H2SO4 / acetone
View Scheme
(+/-)-13-ethyl-3-methoxygona-1,3,5(10),8-tetraen-17β-ol

(+/-)-13-ethyl-3-methoxygona-1,3,5(10),8-tetraen-17β-ol

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Py
2: KOH / methanol
3: Li, liq. NH3 / diethyl ether; dioxane
4: CrO3, aq. H2SO4 / acetone
View Scheme
methanol
67-56-1

methanol

13β-ethyl-gon-4-en-3,17-dione
21800-83-9

13β-ethyl-gon-4-en-3,17-dione

A

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

B

13-Ethyl-3-methoxygona-1,3,5(10),9(11)-tetraen-17-one
19882-75-8

13-Ethyl-3-methoxygona-1,3,5(10),9(11)-tetraen-17-one

C

D-(+)-13β-ethyl-3-methoxygona-1,3,5(10)-triene-6,17-dione

D-(+)-13β-ethyl-3-methoxygona-1,3,5(10)-triene-6,17-dione

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; iodine for 2.5h; Heating; Yields of byproduct given;A n/a
B n/a
C 0.38 g
...Expand
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

3-Methoxy-18-methyl-17-tosylhydrazono-1,3,5(10)-oestratrien
59126-70-4

3-Methoxy-18-methyl-17-tosylhydrazono-1,3,5(10)-oestratrien

Conditions
ConditionsYield
With sulfuric acid In methanol for 14h; Heating;88%
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

acetylene
74-86-2

acetylene

13β-ethyl-3-methoxy-17α-ethynyl-gona-1,3,5(10)-trien-17β-ol
14009-70-2

13β-ethyl-3-methoxy-17α-ethynyl-gona-1,3,5(10)-trien-17β-ol

Conditions
ConditionsYield
Stage #1: acetylene With potassium tert-butylate In tetrahydrofuran at 0 - 5℃; for 2h;
Stage #2: dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one In tetrahydrofuran at 0 - 5℃;		78.3%
With lithium; ethylenediamine In tetrahydrofuran
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

(17S)-13β-Ethyl-3-methoxy-1,3,5(10)-gonatrien-17-spirooxiran
87080-88-4

(17S)-13β-Ethyl-3-methoxy-1,3,5(10)-gonatrien-17-spirooxiran

Conditions
ConditionsYield
73%
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

13-ethyl-3-methoxygonan-1,3,15-trien-17-ol

13-ethyl-3-methoxygonan-1,3,15-trien-17-ol

Conditions
ConditionsYield
With 1-[4-(N,N-dimethylamino)phenyl]ethanol; zirconium(IV) tert-butoxide In toluene at 23℃; for 120h;19%
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

(8R,9S,13S,14S)-13-Ethyl-3-methoxy-17-methylene-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene

(8R,9S,13S,14S)-13-Ethyl-3-methoxy-17-methylene-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene

Conditions
ConditionsYield
(i) PhLi, (ii) /BRN= 2059135/; Multistep reaction;
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

1,4-Dichloro-2-butyne
821-10-3

1,4-Dichloro-2-butyne

methyl iodide
74-88-4

methyl iodide

(8R,9S,13S,14S,17S)-13-Ethyl-3-methoxy-17-penta-1,3-diynyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol

(8R,9S,13S,14S,17S)-13-Ethyl-3-methoxy-17-penta-1,3-diynyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol

Conditions
ConditionsYield
(i) NaNH2, liq. NH3, (ii) /BRN= 969135/, (iii) /BRN= 2059135/, THF; Multistep reaction;
...Expand
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

3-Methoxy-18-methyl-1,3,5(10),16-oestratetraen
59126-71-5

3-Methoxy-18-methyl-1,3,5(10),16-oestratetraen

Conditions
ConditionsYield
With methyllithium In diethyl ether for 4h; Ambient temperature; Yield given;
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

phenyllithium
591-51-5

phenyllithium

13α-Ethyl-3-methoxy-17-phenyl-1,3,5(10),14(15),16(17)-gonapentaene
126971-24-2

13α-Ethyl-3-methoxy-17-phenyl-1,3,5(10),14(15),16(17)-gonapentaene

Conditions
ConditionsYield
With trifluoroacetic acid 1.) THF, benzene, -78 deg C, 15 min; r.t., 30 min, 2.) CH2CL2, r.t., 1 h; Yield given. Multistep reaction;
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

13β-ethyl-3-hydroxygona-1,3,5(10)-trien-17-one
6544-68-9

13β-ethyl-3-hydroxygona-1,3,5(10)-trien-17-one

Conditions
ConditionsYield
With pyridine; hydrogenchloride at 180℃;
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

16α,17α-Epoxy-3-methoxy-18-methyl-1,3,5(10)-oestratrien
59126-72-6

16α,17α-Epoxy-3-methoxy-18-methyl-1,3,5(10)-oestratrien

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
View Scheme
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

3-Methoxy-18-methyl-1,3,5(10),15-oestratetraen-17α-ol
59126-63-5

3-Methoxy-18-methyl-1,3,5(10),15-oestratetraen-17α-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 87 percent / ethane-1,2-diol / 24 h / 120 °C
4: m-chlorperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 2 h / Ambient temperature
5: 30 percent / o-xylene / 33 h / 140 °C
View Scheme
Multi-step reaction with 3 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 65 percent / diphenyl diselenide, NaBH4 / ethanol / 18 h / Heating
View Scheme
Multi-step reaction with 5 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 59 percent / lithium bromide / acetic acid / 2 h / Ambient temperature
4: 88 percent / phosphor trichloride oxide / tetrahydrofuran / 18 h / Ambient temperature
5: 1) 1,8-diazobicyclo<5.4.0>undec-7-en; 2) oxalic acid / 1) 30 h at 140 deg C; 2) methanol, water, 24 h at room temp.
View Scheme
Multi-step reaction with 5 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 79 percent / NaBH4 / ethanol / 80 °C / 1) 20 min.; 2) 17 h
4: 12 percent / NaIO4 / methanol; CH2Cl2 / 48 h / Ambient temperature
5: 50 percent / NaCO3 / o-xylene / 20 h / 140 °C
View Scheme
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

16β-Brom-3-methoxy-18-methyl-1,3,5(10)-oestratrien-17α-ol
59126-79-3

16β-Brom-3-methoxy-18-methyl-1,3,5(10)-oestratrien-17α-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 59 percent / lithium bromide / acetic acid / 2 h / Ambient temperature
View Scheme
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

3-Methoxy-18-methyl-1,3,5(10),14,16-oestrapentaen
80904-55-8

3-Methoxy-18-methyl-1,3,5(10),14,16-oestrapentaen

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 87 percent / ethane-1,2-diol / 24 h / 120 °C
4: m-chlorperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 2 h / Ambient temperature
5: 30 percent / o-xylene / 33 h / 140 °C
6: 55 percent / 70 percent HClO4 / acetone / 0.33 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 65 percent / diphenyl diselenide, NaBH4 / ethanol / 18 h / Heating
4: 55 percent / 70 percent HClO4 / acetone / 0.33 h / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 59 percent / lithium bromide / acetic acid / 2 h / Ambient temperature
4: 88 percent / phosphor trichloride oxide / tetrahydrofuran / 18 h / Ambient temperature
5: 1) 1,8-diazobicyclo<5.4.0>undec-7-en; 2) oxalic acid / 1) 30 h at 140 deg C; 2) methanol, water, 24 h at room temp.
6: 55 percent / 70 percent HClO4 / acetone / 0.33 h / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 79 percent / NaBH4 / ethanol / 80 °C / 1) 20 min.; 2) 17 h
4: 12 percent / NaIO4 / methanol; CH2Cl2 / 48 h / Ambient temperature
5: 50 percent / NaCO3 / o-xylene / 20 h / 140 °C
6: 55 percent / 70 percent HClO4 / acetone / 0.33 h / Ambient temperature
View Scheme
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

3-Methoxy-18-methyl-16β-phenylthio-1,3,5(10)-oestratrien-17α-ol
80904-56-9

3-Methoxy-18-methyl-16β-phenylthio-1,3,5(10)-oestratrien-17α-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 79 percent / NaBH4 / ethanol / 80 °C / 1) 20 min.; 2) 17 h
View Scheme
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

3-Methoxy-18-methyl-16β-phenylselenyl-1,3,5(10)-oestratrien-17α-ol
80904-57-0

3-Methoxy-18-methyl-16β-phenylselenyl-1,3,5(10)-oestratrien-17α-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 95 percent / NaBH4 / ethanol / 1) room temp.; 2) reflux at 20 h
View Scheme
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

3-Methoxy-18-methyl-16β-piperidino-1,3,5(10)-oestratien-17α-ol
80904-53-6

3-Methoxy-18-methyl-16β-piperidino-1,3,5(10)-oestratien-17α-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 87 percent / ethane-1,2-diol / 24 h / 120 °C
View Scheme
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

N-(17α-Hydroxy-3-methoxy-1,3,5(10)-oestratrien-16β-yl)piperidin-N-oxid
80904-54-7

N-(17α-Hydroxy-3-methoxy-1,3,5(10)-oestratrien-16β-yl)piperidin-N-oxid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 87 percent / ethane-1,2-diol / 24 h / 120 °C
4: m-chlorperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 2 h / Ambient temperature
View Scheme
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

16β-Brom-3-methoxy-18-methyl-17α-(tetrahydro-2-pyranyloxy)-1,3,5(10)-oestratrien
59126-80-6

16β-Brom-3-methoxy-18-methyl-17α-(tetrahydro-2-pyranyloxy)-1,3,5(10)-oestratrien

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 59 percent / lithium bromide / acetic acid / 2 h / Ambient temperature
4: 88 percent / phosphor trichloride oxide / tetrahydrofuran / 18 h / Ambient temperature
View Scheme
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

3-Methoxy-18-methyl-16β-phenylsulfonyl-1,3,5(10)-oestratrien-17α-ol
80904-62-7

3-Methoxy-18-methyl-16β-phenylsulfonyl-1,3,5(10)-oestratrien-17α-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 79 percent / NaBH4 / ethanol / 80 °C / 1) 20 min.; 2) 17 h
4: 4 percent / NaIO4 / methanol; CH2Cl2 / 48 h / Ambient temperature
View Scheme
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

3-Methoxy-18-methyl-16β-phenylselenonyl-1,3,5(10)-oestratrien-17α-ol
80904-63-8

3-Methoxy-18-methyl-16β-phenylselenonyl-1,3,5(10)-oestratrien-17α-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 95 percent / NaBH4 / ethanol / 1) room temp.; 2) reflux at 20 h
4: 6 percent / m-chlorperbenzoic acid / CH2Cl2 / 0.25 h / -40 °C
View Scheme
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

(S)-3-Methoxy-18-methyl-16β-phenylsulfinyl-1,3,5(10)-oestratrien-17α-ol
80904-58-1, 80904-60-5

(S)-3-Methoxy-18-methyl-16β-phenylsulfinyl-1,3,5(10)-oestratrien-17α-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 79 percent / NaBH4 / ethanol / 80 °C / 1) 20 min.; 2) 17 h
4: 34 percent / NaIO4 / methanol; CH2Cl2 / 48 h / Ambient temperature
View Scheme
dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one
848-04-4

dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17-one

(R)-3-Methoxy-18-methyl-16β-phenylsulfinyl-1,3,5(10)-oestratrien-17α-ol
80904-58-1, 80904-60-5

(R)-3-Methoxy-18-methyl-16β-phenylsulfinyl-1,3,5(10)-oestratrien-17α-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methyl lithium / diethyl ether / 4 h / Ambient temperature
2: 79 percent / 4-nitroperbenzoic acid / 1,2-dichloro-ethane; 2-methyl-propan-2-ol / 18 h / Ambient temperature
3: 79 percent / NaBH4 / ethanol / 80 °C / 1) 20 min.; 2) 17 h
4: 12 percent / NaIO4 / methanol; CH2Cl2 / 48 h / Ambient temperature
View Scheme

Ethylmetrienone Specification

The Ethylmetrienone with its cas register number is 848-04-4. It also can be called as 13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-one and the Systematic name about this chemical is (8R,9S,13S,14S)-13-ethyl-3-methoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one.

Physical properties about Ethylmetrienone are: (1)ACD/LogP: 4.97; (2)ACD/LogD (pH 5.5): 5; (3)ACD/LogD (pH 7.4): 5; (4)ACD/BCF (pH 5.5): 2964; (5)ACD/BCF (pH 7.4): 2964; (6)ACD/KOC (pH 5.5): 10637; (7)ACD/KOC (pH 7.4): 10637; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 26.3Å2; (11)Index of Refraction: 1.548; (12)Molar Refractivity: 87.462 cm3; (13)Molar Volume: 275.301 cm3; (14)Polarizability: 34.673x10-24cm3; (15)Surface Tension: 39.057 dyne/cm; (16)Enthalpy of Vaporization: 69.692 kJ/mol.

You can still convert the following datas into molecular structure:
(1)SMILES: CCC12CCC3c4ccc(cc4CCC3C1CCC2=O)OC
(2)InChI: InChI=1/C20H26O2/c1-3-20-11-10-16-15-7-5-14(22-2)12-13(15)4-6-17(16)18(20)8-9-19(20)21/h5,7,12,16-18H,3-4,6,8-11H2,1-2H3/t16-,17-,18+,20+/m1/s1
(3)InChIKey: FHJVQLWFUQMADH-XSYGEPLQBF
(4)Std. InChI: InChI=1S/C20H26O2/c1-3-20-11-10-16-15-7-5-14(22-2)12-13(15)4-6-17(16)18(20)8-9-19(20)21/h5,7,12,16-18H,3-4,6,8-11H2,1-2H3/t16-,17-,18+,20+/m1/s1
(5)Std. InChIKey: FHJVQLWFUQMADH-XSYGEPLQSA-N

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