Gestonorone supplier | CasNO.2137-18-0

Name
Gestonorone
EINECS 218-378-2
CAS No. 2137-18-0
Article Data13
CAS DataBase
Density 1.17 g/cm³
Solubility
Melting Point 222-224 °C
Formula C₂₀H₂₈O₃
Boiling Point 484.9 °C at 760 mmHg
Molecular Weight 316.441
Flash Point 261.2 °C
Transport Information
Appearance White or almost white crystalline powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 17-Hydroxy-19-norpregn-4-ene-3,20-dione;17a-Hydroxy-19-norprogesterone;TX 045;
PSA 54.37000
LogP 3.44830

Synthetic route

: C20H27ClO3

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
With iron; acetic acid at 60℃; for 3h; Reagent/catalyst; Temperature;	97.97%

: 14339-99-2
20,20-ethanediyldioxy-3-methoxy-19-nor-pregna-2,5(10)-dien-17-ol

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
With hydrogenchloride

: 1624-58-4
17α-hydroxy-3-methoxy-19-norpregna-1,3,5(10)-trien-20-one

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: benzene; toluene-4-sulfonic acid / Entfernen des entstehenden Wassers 2: diethyl ether; lithium; liquid ammonia / anschliessend Behandeln mit Aethanol 3: methanol.HCl View Scheme
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C 2: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere 3: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C View Scheme

: 101766-63-6
3-hydroxy-19-norpregna-1,3,5(10),16-tetraen-20-one

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: methanol; aqueous hydrogen peroxide; aq. NaOH solution 2: ethanol; aqueous KOH-solution 3: HBr; acetic acid / Hydrierung an Palladium/CaCO3 in Aethanol 4: benzene; toluene-4-sulfonic acid / Entfernen des entstehenden Wassers 5: diethyl ether; lithium; liquid ammonia / anschliessend Behandeln mit Aethanol 6: methanol.HCl View Scheme

: 67519-64-6
16α,17α-epoxy-17-acetyl-Δ1,3,5(10)-estratriene

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: ethanol; aqueous KOH-solution 2: HBr; acetic acid / Hydrierung an Palladium/CaCO3 in Aethanol 3: benzene; toluene-4-sulfonic acid / Entfernen des entstehenden Wassers 4: diethyl ether; lithium; liquid ammonia / anschliessend Behandeln mit Aethanol 5: methanol.HCl View Scheme

: 111979-17-0
16α,17-epoxy-3-methoxy-19-nor-pregna-1,3,5(10)-trien-20-one

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: HBr; acetic acid / Hydrierung an Palladium/CaCO3 in Aethanol 2: benzene; toluene-4-sulfonic acid / Entfernen des entstehenden Wassers 3: diethyl ether; lithium; liquid ammonia / anschliessend Behandeln mit Aethanol 4: methanol.HCl View Scheme

: 14328-46-2
20,20-(ethylenedioxy)-3-methoxy-17α-hydroxy-19-norpregna-1,3,5(10)-triene

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether; lithium; liquid ammonia / anschliessend Behandeln mit Aethanol 2: methanol.HCl View Scheme
Multi-step reaction with 2 steps 1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere 2: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C View Scheme

: 53-16-7
Estrone

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: sodium hydroxide / acetone; water / 2 h / Reflux 2.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C 3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 4.1: sodium methylate / methanol / Reflux 4.2: 2 h / Reflux 5.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C 6.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere 7.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: sodium hydroxide / acetone; water / 2 h / Reflux
2.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C
3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
4.1: sodium methylate / methanol / Reflux
4.2: 2 h / Reflux
5.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C
6.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere
7.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C
View Scheme

: 1624-62-0
estrone 3-methyl ether

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C 2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3.1: sodium methylate / methanol / Reflux 3.2: 2 h / Reflux 4.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C 5.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere 6.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C
2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
3.1: sodium methylate / methanol / Reflux
3.2: 2 h / Reflux
4.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C
5.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere
6.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C
View Scheme

: C22H32O4

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 60℃; for 0.333333h;	18.6 g

: 72-33-3
mestranol

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 2.1: sodium methylate / methanol / Reflux 2.2: 2 h / Reflux 3.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C 4.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere 5.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
2.1: sodium methylate / methanol / Reflux
2.2: 2 h / Reflux
3.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C
4.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere
5.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C
View Scheme

: 3-methoxy-21-(phenylsulfinyl)-19-norpregna-1(2),3(4),5(10),17(20),20-pentaene

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium methylate / methanol / Reflux 1.2: 2 h / Reflux 2.1: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 2 h / 20 °C 3.1: sodium; ammonia / ethanol; water; tetrahydrofuran; tert-butyl alcohol / -60 °C / Inert atmosphere 4.1: hydrogenchloride / water; tetrahydrofuran / 0.33 h / 60 °C View Scheme

: 3-methoxy-17α-[(trimethylsilyl)oxy]estr-2,5(10)-dien-17-carbonitrile

: 917-54-4
methyllithium

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Stage #1: 3-methoxy-17α-[(trimethylsilyl)oxy]estr-2,5(10)-dien-17-carbonitrile; methyllithium With N,N,N,N,-tetramethylethylenediamine In tert-butyl methyl ether at -40 - -30℃; for 1h; Stage #2: With hydrogenchloride In tert-butyl methyl ether at -30 - 25℃; for 16h;	25.67 g

: 17976-32-8
3-methoxyestra-2,5(10)-dien-17-one

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 2,6-di-tert-butyl-4-methyl-phenol / ethanol / 0.17 h / Inert atmosphere 1.2: 17 h / 20 - 63 °C / Inert atmosphere 2.1: 2,6-di-tert-butyl-4-methyl-phenol; 1H-imidazole / tert-butyl methyl ether; tetrahydrofuran / Inert atmosphere 3.1: N,N,N,N,-tetramethylethylenediamine / tert-butyl methyl ether / 1 h / -40 - -30 °C 3.2: 16 h / -30 - 25 °C View Scheme

: C22H33ClO3Si

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium diisobutylamide; chloro-trimethyl-silane; n-butyllithium / dichloromethane; chloroform / 1 h / -50 °C / Inert atmosphere 2: iron; acetic acid / 3 h / 60 °C View Scheme

: 734-32-7
estra-4-ene-3,17-dione

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; Tetrahydrothiopyran-4-one; acetic acid / methanol; ethanol / 25 h / 38 °C / Green chemistry 2: dmap / dichloromethane / 2 h / 32 °C 3: lithium diisobutylamide; chloro-trimethyl-silane; n-butyllithium / dichloromethane; chloroform / 1 h / -50 °C / Inert atmosphere 4: iron; acetic acid / 3 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide; Tetrahydrothiopyran-4-one; acetic acid / methanol; ethanol / 25 h / 38 °C / Green chemistry 2: triethylamine / tetrachloromethane / 2 h / -6 °C 3: lithium diisobutylamide; chloro-trimethyl-silane; n-butyllithium / dichloromethane; chloroform / 1 h / -50 °C / Inert atmosphere 4: iron; acetic acid / 3 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide; Tetrahydrothiopyran-4-one; acetic acid / methanol; ethanol / 25 h / 38 °C / Green chemistry 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 2 h / 0 - 2 °C 3: lithium diisobutylamide; chloro-trimethyl-silane; n-butyllithium / dichloromethane; chloroform / 1 h / -50 °C / Inert atmosphere 4: iron; acetic acid / 3 h / 60 °C View Scheme

: 17β-cyano-17α-hydroxy-19-norandrost-4-en-3-one

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dmap / dichloromethane / 2 h / 32 °C 2: lithium diisobutylamide; chloro-trimethyl-silane; n-butyllithium / dichloromethane; chloroform / 1 h / -50 °C / Inert atmosphere 3: iron; acetic acid / 3 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / tetrachloromethane / 2 h / -6 °C 2: lithium diisobutylamide; chloro-trimethyl-silane; n-butyllithium / dichloromethane; chloroform / 1 h / -50 °C / Inert atmosphere 3: iron; acetic acid / 3 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 2 h / 0 - 2 °C 2: lithium diisobutylamide; chloro-trimethyl-silane; n-butyllithium / dichloromethane; chloroform / 1 h / -50 °C / Inert atmosphere 3: iron; acetic acid / 3 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: dmap; 1H-imidazole / toluene; acetone / 2 h / -1 - 0 °C 2: lithium diisobutylamide; chloro-trimethyl-silane; n-butyllithium / dichloromethane; chloroform / 1 h / -50 °C / Inert atmosphere 3: iron; acetic acid / 3 h / 60 °C View Scheme

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 108-24-7
acetic anhydride

: 31981-44-9
17α-acetoxy-19-norpregna-4-ene-3,20-dione

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 24h;	95%
With toluene-4-sulfonic acid und Behandeln des Reaktionsprodukts mit methanol.KOH;
With toluene-4-sulfonic acid und Behandeln des Reaktionsprodukts mit methanol.HCl;

: 108-22-5
Isopropenyl acetate

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 31981-44-9
17α-acetoxy-19-norpregna-4-ene-3,20-dione

Conditions

Conditions	Yield
Stage #1: Isopropenyl acetate; 17-alpha-Hydroxy-19-norprogesterone With toluene-4-sulfonic acid In dichloromethane; chloroform at 58 - 60℃; for 2h; Stage #2: With hydrogenchloride In dichloromethane; chloroform; water at 60℃; Solvent; Temperature;	82.36%

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 122-51-0
orthoformic acid triethyl ester

: 3-ethoxy-17α-hydroxy-19-norpregna-4-en-20-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 20 - 80℃; for 1h;	82%

: 2051-49-2
n-hexanoic anhydride

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 1253-28-7
gestonorone caproate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid und anscliessendes Erwaermen mit methanol.HCl;

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 54947-44-3
11β,17,21-trihydroxy-19-nor-pregn-4-ene-3,20-dione

Conditions

Conditions	Yield
mit Hilfe von Homogenaten aus Nebennieren;
Multi-step reaction with 3 steps 1: THF; methanol; iodine / anschliessendes Behandeln mit wss.NaOH und Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton 2: aqueous methanol.KHCO3 3: mit Hilfe von Homogenaten aus Nebennieren View Scheme

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 124263-28-1
21-acetoxy-17-hydroxy-19-nor-pregn-4-ene-3,20-dione

Conditions

Conditions	Yield
With tetrahydrofuran; methanol; iodine anschliessendes Behandeln mit wss.NaOH und Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton;

: 64-18-6
formic acid

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 108-24-7
acetic anhydride

: 13635-19-3
17-formyloxy-19-nor-pregn-4-ene-3,20-dione

Conditions

Conditions	Yield
With toluene-4-sulfonic acid

...Expand

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 15313-96-9
11β-hydroxy-estr-4-ene-3,17-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: mit Hilfe von Homogenaten aus Nebennieren 2: NaBiO3; aqueous acetic acid View Scheme
Multi-step reaction with 4 steps 1: THF; methanol; iodine / anschliessendes Behandeln mit wss.NaOH und Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton 2: aqueous methanol.KHCO3 3: mit Hilfe von Homogenaten aus Nebennieren 4: NaBiO3; aqueous acetic acid View Scheme

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 115184-02-6
17,21-dihydroxy-19-nor-pregn-4-ene-3,20-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: THF; methanol; iodine / anschliessendes Behandeln mit wss.NaOH und Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton 2: aqueous methanol.KHCO3 View Scheme

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 111901-74-7
17,21-dihydroxy-19-nor-pregn-4-ene-3,11,20-trione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: mit Hilfe von Homogenaten aus Nebennieren 2: CrO3; acetic acid View Scheme
Multi-step reaction with 4 steps 1: THF; methanol; iodine / anschliessendes Behandeln mit wss.NaOH und Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton 2: aqueous methanol.KHCO3 3: mit Hilfe von Homogenaten aus Nebennieren 4: CrO3; acetic acid View Scheme

kieselguhr: kieselguhr

: 505-84-0
dipropoxymethane

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 17α-propoxymethoxy-19-nor-4-pregnene-3,20-dione

Conditions

Conditions	Yield
With phosphorus pentaoxide In dichloromethane

...Expand

kieselguhr: kieselguhr

: 462-95-3
formaldehyde diethyl acetal

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 17α-ethoxymethoxy-19-nor-4-pregnene-3,20-dione

Conditions

Conditions	Yield
With phosphorus pentaoxide In dichloromethane

...Expand

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 17α-methoxymethoxy-19-nor-4-pregnene-3,20-dione

Conditions

Conditions	Yield
In Dimethoxymethane

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 3-ethoxy-17α-acetoxy-19-norpregna-3,5-diene-20-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / 24 h / 20 °C 2: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C View Scheme

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 147508-40-5
6-formyl-3-ethoxy-17α-acetoxy-19-norpregna-3,5-diene-20-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / 24 h / 20 °C 2: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C 3: trichlorophosphate / -10 °C View Scheme

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 58652-19-0
17α-acetoxy-6-methylene-19-norpregn-4-ene-3,20-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / 24 h / 20 °C 2: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C 3: trichlorophosphate / -10 °C 4: sodium tetrahydroborate / methanol / 20 °C View Scheme

: 2137-18-0
17-alpha-Hydroxy-19-norprogesterone

: 58652-20-3
nomegestrol acetate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: toluene-4-sulfonic acid / 24 h / 20 °C 2: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C 3: trichlorophosphate / -10 °C 4: sodium tetrahydroborate / methanol / 20 °C 5: 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 0.75 h / Reflux View Scheme

Gestonorone Specification

The Gestonorone , its cas register number is 2137-18-0. The IUPAC name about this chemicals is (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one . Following are the physical and chemical properties about it: (1)Index of Refraction: 1.564 ; (2)Molar Refractivity: 87.86 cm³ ; (3)Molar Volume: 270.1 cm³ ; (4)Surface Tension: 47.4 dyne/cm ; (5)Enthalpy of Vaporization: 86.45 kJ/mol ; (6)Vapour Pressure: 1.95E-11 mmHg at 25°C .This chemicals belongs to the Steroids.

The Gestonorone is a white or almost white crystalline powder.It is progesterone medicines, a major role in the hypothalamus and pituitary by inhibiting pituitary gonadotropin secretion, so that follicle-stimulating hormone and luteinizing hormone levels lower or disappear, inhibiting ovulation; on the endometrium are also strong inhibition, affecting Yunluan implantation. Used for emergency contraception, the strong by suppressing follicular development, inhibit or delay ovulation, influence endometrial development, interfering with implantation of different sectors to achieve the purpose of avoiding pregnancy.

This chemicals can be described computed from structure:
(1)Canonical SMILES: CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)O
(2)Isomeric SMILES: CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)O
(3)InChI: InChI=1S/C20H28O3/c1-12(21)20(23)10-8-18-17-5-3-13-11-14(22)4-6-15(13)16(17)7-9-19(18,20)2/h11,15-18,23H,3-10H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1
(4)InChIKey: GTFUITFQDGVJSK-XGXHKTLJSA-N

Product Name

Gestonorone

Synthetic route

Gestonorone Specification

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