gestodene
Conditions | Yield |
---|---|
With hydrogenchloride In acetone at 20℃; for 0.75h; | 90% |
17α-ethynyl-18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5,15-estradien-17β-ol
gestodene
Conditions | Yield |
---|---|
Stage #1: 17α-ethynyl-18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5,15-estradien-17β-ol; 3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-17α-ethnyl-17β-hydroxy-18-methyl-10,15-estradiene With water; hydrogenchloride In acetone at 20℃; for 0.75h; Stage #2: With sodium hydrogencarbonate In water; acetone pH=7; Product distribution / selectivity; | 90% |
3-ethoxy-18-methyl-estra-3,5,15-trien-17-one
acetylenemagnesium bromide
gestodene
Conditions | Yield |
---|---|
Stage #1: 3-ethoxy-18-methyl-estra-3,5,15-trien-17-one; acetylenemagnesium bromide In tetrahydrofuran; 2-MeTHF at 20 - 25℃; for 2h; Stage #2: With hydrogenchloride In ethanol; water at 7 - 10℃; for 2h; | 80% |
17α-Ethinyl-3,3-ethylendithio-18-methyl-4,15-estradien-17β-ol
gestodene
Conditions | Yield |
---|---|
With calcium carbonate; methyl iodide In methanol; water for 20h; Heating; | 68% |
ethylene glycol
15α-Acetoxy-18-methyl-4-estren-3,17-dion
acetylene
gestodene
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF/hexane, -70 deg C, 10 min, 2.) -70 deg C, 1 h; Yield given. Multistep reaction; |
15α-Acetoxy-3-methoxy-18-methyl-3,5-estradien-17-on
acetylene
gestodene
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
13β-ethyl-gon-4-en-3,17-dione
gestodene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 90 percent / triethyl orthoformate; p-TsOH / CH2Cl2 / 3 h / 10 °C 2.1: t-BuOK / tetrahydrofuran / 0.17 h / 20 °C 2.2: tetrahydrofuran / 2 h / 20 °C 3.1: Et3N / xylene / 2.5 h / 140 °C 4.1: 94 percent / tetrahydrofuran / 2 h / 0 °C 5.1: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1: 90 percent / triethyl orthoformate; p-TsOH / CH2Cl2 / 3 h / 10 °C 2: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 - 20 °C 3: MCPBA / CH2Cl2 / 0.5 h / -78 °C 4: Et3N / xylene / 2.5 h / 140 °C 5: 94 percent / tetrahydrofuran / 2 h / 0 °C 6: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: 77.2 percent / mushroom Penicillium raistrickii (ATCC 10490) / H2O; various solvent(s) / 70 h / 30 °C 2: 96 percent / pyridine / 1 h View Scheme |
gestodene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 94 percent / tetrahydrofuran / 2 h / 0 °C 2: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme |
gestodene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: t-BuOK / tetrahydrofuran / 0.17 h / 20 °C 1.2: tetrahydrofuran / 2 h / 20 °C 2.1: Et3N / xylene / 2.5 h / 140 °C 3.1: 94 percent / tetrahydrofuran / 2 h / 0 °C 4.1: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 - 20 °C 2: MCPBA / CH2Cl2 / 0.5 h / -78 °C 3: Et3N / xylene / 2.5 h / 140 °C 4: 94 percent / tetrahydrofuran / 2 h / 0 °C 5: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme |
gestodene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: MCPBA / CH2Cl2 / 0.5 h / -78 °C 2: Et3N / xylene / 2.5 h / 140 °C 3: 94 percent / tetrahydrofuran / 2 h / 0 °C 4: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme |
gestodene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Et3N / xylene / 2.5 h / 140 °C 2: 94 percent / tetrahydrofuran / 2 h / 0 °C 3: 90 percent / aq. HCl / acetone / 0.75 h / 20 °C View Scheme |
15α-Hydroxy-18-methyl-4-estren-3,17-dion
gestodene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 96 percent / pyridine / 1 h View Scheme | |
Multi-step reaction with 3 steps 1: 96 percent / pyridine / 1 h 2: 84 percent / 4-CH3-C6H6-SO3H*C5H5N / 6 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: 98 percent / BF3*Et2O / methanol / Ambient temperature 2: pyridine / 3.5 h / 0 °C 3: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature 4: 1.) 15 percent BuLi / 1.) hexane, THF, 0 deg C, 2.) 30 min 5: 68 percent / CH3I, CaCO3 / methanol; H2O / 20 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: pyridine / 3.5 h / 0 °C 2: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature 3: 1.) 15 percent BuLi / 1.) THF/hexane, -70 deg C, 10 min, 2.) -70 deg C, 1 h View Scheme |
3,3-Ethylendithio-18-methyl-4,15-estradien-17-on
gestodene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) 15 percent BuLi / 1.) hexane, THF, 0 deg C, 2.) 30 min 2: 68 percent / CH3I, CaCO3 / methanol; H2O / 20 h / Heating View Scheme |
3,3-Ethylendithio-15α-hydroxy-18-methyl-4-estren-17-on
gestodene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pyridine / 3.5 h / 0 °C 2: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature 3: 1.) 15 percent BuLi / 1.) hexane, THF, 0 deg C, 2.) 30 min 4: 68 percent / CH3I, CaCO3 / methanol; H2O / 20 h / Heating View Scheme |
15α-Acetoxy-18-methyl-4-estren-3,17-dion
gestodene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 84 percent / 4-CH3-C6H6-SO3H*C5H5N / 6 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / ethanol / 1 h / 20 °C 2.1: toluene-4-sulfonic acid; orthoformic acid triethyl ester / 1 h / 20 °C 2.2: 2 h / 40 °C 3.1: tetrahydrofuran; 2-MeTHF / 2 h / 20 - 25 °C 3.2: 2 h / 7 - 10 °C View Scheme |
Methanesulfonic acid (8R,9S,10R,13S,14S,15S)-13-ethyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-15-yl ester
gestodene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature 2: 1.) 15 percent BuLi / 1.) THF/hexane, -70 deg C, 10 min, 2.) -70 deg C, 1 h View Scheme |
C22H32O4S3
gestodene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaOAc / pyridine; dimethylformamide / 20 h / Ambient temperature 2: 1.) 15 percent BuLi / 1.) hexane, THF, 0 deg C, 2.) 30 min 3: 68 percent / CH3I, CaCO3 / methanol; H2O / 20 h / Heating View Scheme |
15α-Acetoxy-3-methoxy-18-methyl-3,5-estradien-17-on
gestodene
Conditions | Yield |
---|---|
Product distribution / selectivity; |
Conditions | Yield |
---|---|
With oxalic acid; magnesium In tetrahydrofuran; methanol; water |
15α-acetoxy-3-ethoxy-18-methyl-estra-3,5-dien-17-one
gestodene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid; orthoformic acid triethyl ester / 1 h / 20 °C 1.2: 2 h / 40 °C 2.1: tetrahydrofuran; 2-MeTHF / 2 h / 20 - 25 °C 2.2: 2 h / 7 - 10 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: 15α-Acetoxy-18-methyl-4-estren-3,17-dion With hydrogenchloride; propylene glycol In 1,4-dioxane; 1,2-dimethoxyethane at -20℃; for 4h; Stage #2: With toluene-4-sulfonic acid; trimethyl orthoformate In methanol at 20℃; for 3h; Stage #3: acetylene Further stages; | 8.17 g |
gestodene
17α-Bromethinyl-17β-hydroxy-18-methyl-4,15-oestradien-3-on
Conditions | Yield |
---|---|
With N-Bromosuccinimide; silver nitrate In acetone for 0.25h; Ambient temperature; | 82% |
gestodene
17β-Hydroxy-17α-iodethinyl-18-methyl-4,15-oestradien-3-on
Conditions | Yield |
---|---|
With N-iodo-succinimide; silver nitrate In acetone for 0.25h; Ambient temperature; | 77% |
gestodene
Conditions | Yield |
---|---|
With hydrogenchloride at 80℃; for 2h; | 1.55 g |
gestodene
Conditions | Yield |
---|---|
With 4-pyrrolidin-1-ylpyridine In pyridine; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; propionic acid anhydride |
Conditions | Yield |
---|---|
With 4-pyrrolidin-1-ylpyridine In pyridine; water |
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane; acetone; benzene |
Conditions | Yield |
---|---|
In benzene |
gestodene
trifluoroacetic anhydride
Conditions | Yield |
---|---|
In dichloromethane; acetone; benzene |
gestodene
Conditions | Yield |
---|---|
With acetic anhydride In 2,3,5-trimethyl-pyridine; hydrogenchloride |
IUPAC Name: (8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one
Molecular Formula: C21H26O2
Molecular Weight: 310.43 g/mol
SMILES: C1[C@@]2([C@@H]([C@@H]3[C@@H]([C@@H]4C(=CC(=O)CC4)CC3)C1)C=C[C@]2(C#C)O)CC
InChI: InChI=1/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16?,17?,18?,19?,20?,21-/m0/s1
EINECS: 262-145-8
Classification Code: Contraceptive Agents; Contraceptive Agents, Female; Contraceptives, Oral; Contraceptives, oral, synthetic; Hormone; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Progestin; Progestins; Reproductive Control Agents; Reproductive Effect
Product Categories: Miscellaneous Biochemicals; Hormone; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids
Index of Refraction: 1.588
Molar Refractivity: 90.09 cm3
Molar Volume: 267.6 cm3
Polarizability: 35.71×10-24 cm3
Surface Tension: 49.7 dyne/cm
Density: 1.15 g/cm3
Flash Point: 196.9 °C
Enthalpy of Vaporization: 83.47 kJ/mol
Boiling Point: 462.7 °C at 760 mmHg
Melting Point: 190-192 °C
Vapour Pressure of Gestodene (CAS NO.60282-87-3): 1.66E-10 mmHg at 25 °C
Gestodene (CAS NO.60282-87-3) is used as orally active gestogen with progesterone-like profile of activity and is used as a contraceptive.
Gestodene (CAS NO.60282-87-3), its Synonyms are 13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregna-4,15-dien-20-yn-3-one ; 17-alpha-Ethinyl-13-ethyl-17-beta-hydroxy-4,15-gonadien-3-one ; Gestodeno ; Gestodenum ; 18,19-Dinorpregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17-alpha)- ; Pregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-18,19-dinor-, (17alpha)- . It is white crystalline solid.
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