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CAS No.: | 2137-18-0 |
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Name: | Gestonorone |
Article Data: | 13 |
Molecular Structure: | |
Formula: | C20H28O3 |
Molecular Weight: | 316.441 |
Synonyms: | 17-Hydroxy-19-norpregn-4-ene-3,20-dione;17a-Hydroxy-19-norprogesterone;TX 045; |
EINECS: | 218-378-2 |
Density: | 1.17 g/cm3 |
Melting Point: | 222-224 °C |
Boiling Point: | 484.9 °C at 760 mmHg |
Flash Point: | 261.2 °C |
Appearance: | White or almost white crystalline powder |
PSA: | 54.37000 |
LogP: | 3.44830 |
17-alpha-Hydroxy-19-norprogesterone
Conditions | Yield |
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With iron; acetic acid at 60℃; for 3h; Reagent/catalyst; Temperature; | 97.97% |
20,20-ethanediyldioxy-3-methoxy-19-nor-pregna-2,5(10)-dien-17-ol
17-alpha-Hydroxy-19-norprogesterone
Conditions | Yield |
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With hydrogenchloride |
17α-hydroxy-3-methoxy-19-norpregna-1,3,5(10)-trien-20-one
17-alpha-Hydroxy-19-norprogesterone
Conditions | Yield |
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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 |
3-hydroxy-19-norpregna-1,3,5(10),16-tetraen-20-one
17-alpha-Hydroxy-19-norprogesterone
Conditions | Yield |
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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 |
16α,17α-epoxy-17-acetyl-Δ1,3,5(10)-estratriene
17-alpha-Hydroxy-19-norprogesterone
Conditions | Yield |
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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 |
16α,17-epoxy-3-methoxy-19-nor-pregna-1,3,5(10)-trien-20-one
17-alpha-Hydroxy-19-norprogesterone
Conditions | Yield |
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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 |
20,20-(ethylenedioxy)-3-methoxy-17α-hydroxy-19-norpregna-1,3,5(10)-triene
17-alpha-Hydroxy-19-norprogesterone
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 |
Conditions | Yield |
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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 |
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 |
17-alpha-Hydroxy-19-norprogesterone
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; water at 60℃; for 0.333333h; | 18.6 g |
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