Conditions | Yield |
---|---|
With sodium carbonate; trifluoroacetic anhydride In benzene for 0.5h; Ambient temperature; | 96.5% |
Stage #1: acetic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 20℃; for 0.5h; Inert atmosphere; Stage #2: norethisterone With dmap In chloroform for 18h; Inert atmosphere; Reflux; | 93% |
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; | 91.6% |
In trifluoroacetic acid | 90% |
With benzenesulfonyl chloride In pyridine for 48h; | 79% |
Conditions | Yield |
---|---|
With pyridine; dmap In 1,2-dichloro-ethane at 0℃; | 92% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 50℃; | 91% |
scandium tris(trifluoromethanesulfonate) In acetonitrile | 86% |
With dmap In toluene at 80 - 90℃; for 3h; | 28 g |
Conditions | Yield |
---|---|
With tetrahydrofuran; potassium hydroxide | |
With hydrogenchloride |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: methanol.KOH; THF View Scheme | |
Multi-step reaction with 2 steps 1: acetic anhydride; toluene-4-sulfonic acid 2: tetrahydrofuran; methanol View Scheme |
Conditions | Yield |
---|---|
In tetrahydrofuran; methanol | |
In tetrahydrofuran; methanol |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: ammonium chloride; lithium / tetrahydrofuran; ethanol; ammonia; water 2: aluminum isopropoxide; sodium sulfate / methanol; water; cyclohexanone; toluene 3: 1,4-dioxane; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ISOPROPYLAMIDE 4: hydrogenchloride / methanol; water 5: acetic anhydride; toluene-4-sulfonic acid 6: tetrahydrofuran; methanol View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aluminum isopropoxide; sodium sulfate / methanol; water; cyclohexanone; toluene 2: 1,4-dioxane; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ISOPROPYLAMIDE 3: hydrogenchloride / methanol; water 4: acetic anhydride; toluene-4-sulfonic acid 5: tetrahydrofuran; methanol View Scheme |
3-methoxyestra-2,5(10)-dien-17-one
norethisterone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1,4-dioxane; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ISOPROPYLAMIDE 2: hydrogenchloride / methanol; water 3: acetic anhydride; toluene-4-sulfonic acid 4: tetrahydrofuran; methanol View Scheme |
3-methoxy-19-nor-17βH-pregna-2,5(10)-dien-20-yn-17-ol
norethisterone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / methanol; water 2: acetic anhydride; toluene-4-sulfonic acid 3: tetrahydrofuran; methanol View Scheme |
3-ethoxy-17α-ethynyl-19-desmethylpregna-3,5-diene-17β-ol
norethisterone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / acetone; water / 10 °C 2: dmap; pyridine / 1,2-dichloro-ethane / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride / acetone; water / 10 °C 2: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride / acetone; water / 10 °C 2: dmap; triethylamine / dichloromethane / 50 °C View Scheme |
norethisterone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C 2: dmap; pyridine / 1,2-dichloro-ethane / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C 2: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C 2: dmap; triethylamine / dichloromethane / 50 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pyridine hydrochloride / 30 °C 2: potassium tert-butylate / acetone / 0 °C 3: hydrogenchloride / tetrahydrofuran; water / 50 °C 4: dmap; pyridine / 1,2-dichloro-ethane / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: pyridine hydrochloride / 30 °C 2: potassium tert-butylate / acetone / 0 °C 3: hydrogenchloride / tetrahydrofuran; water / 50 °C 4: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: pyridine hydrochloride / 30 °C 2: potassium tert-butylate / acetone / 0 °C 3: hydrogenchloride / tetrahydrofuran; water / 50 °C 4: dmap; triethylamine / dichloromethane / 50 °C View Scheme |
3-methoxy-19-norandrosta-3,5-dien-17-one
norethisterone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium tert-butylate / acetone / 0 °C 2: hydrogenchloride / tetrahydrofuran; water / 50 °C 3: dmap; pyridine / 1,2-dichloro-ethane / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium tert-butylate / acetone / 0 °C 2: hydrogenchloride / tetrahydrofuran; water / 50 °C 3: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium tert-butylate / acetone / 0 °C 2: hydrogenchloride / tetrahydrofuran; water / 50 °C 3: dmap; triethylamine / dichloromethane / 50 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium 2-methylpropan-2-olate / tetrahydrofuran / 20 °C 2: hydrogenchloride / acetone; water / 10 °C 3: dmap; pyridine / 1,2-dichloro-ethane / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium 2-methylpropan-2-olate / tetrahydrofuran / 20 °C 2: hydrogenchloride / acetone; water / 10 °C 3: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium 2-methylpropan-2-olate / tetrahydrofuran / 20 °C 2: hydrogenchloride / acetone; water / 10 °C 3: dmap; triethylamine / dichloromethane / 50 °C View Scheme |
norethisterone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium ethoxide / toluene / 50 °C 2: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C 3: dmap; pyridine / 1,2-dichloro-ethane / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium ethoxide / toluene / 50 °C 2: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C 3: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium ethoxide / toluene / 50 °C 2: sulfuric acid / water; 2-methyltetrahydrofuran / 0 °C 3: dmap; triethylamine / dichloromethane / 50 °C View Scheme |
norethisterone acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / tetrahydrofuran; water / 50 °C 2: dmap; pyridine / 1,2-dichloro-ethane / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride / tetrahydrofuran; water / 50 °C 2: dmap; dicyclohexyl-carbodiimide / chloroform / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride / tetrahydrofuran; water / 50 °C 2: dmap; triethylamine / dichloromethane / 50 °C View Scheme |
norethisterone acetate
17β-acetoxy-21,21-dibromo-19-nor-17α-pregn-4-ene-3,20-dione
Conditions | Yield |
---|---|
With water; N-bromoacetamide In tert-butyl alcohol for 4h; Ambient temperature; | 96% |
norethisterone acetate
Conditions | Yield |
---|---|
With silver nitrate In tetrahydrofuran | 81% |
norethisterone acetate
3,21-dioxo-19-norpregna-4,17(20)-dien-20-yl acetate
Conditions | Yield |
---|---|
With oxygen; potassium tetrabromopalladate In 1,2-dimethoxyethane; water at 65℃; for 3h; | 80% |
Conditions | Yield |
---|---|
With copper(I) phenylacetylenide; copper acetylacetonate; triethylamine; copper(l) chloride In tetrahydrofuran at 25℃; for 16h; Irradiation; Inert atmosphere; | 78% |
norethisterone acetate
methyl 3-azidobenzoate
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 8h; Inert atmosphere; | 75% |
para-diiodobenzene
norethisterone acetate
1,4-bis(19-nor-17α-ethynyltestosterone-17β-acetate)benzene
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 4h; Sonogashira coupling; Inert atmosphere; Reflux; | 71% |
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 8h; Inert atmosphere; | 70% |
norethisterone acetate
17,17a-dimethyl-D-homogona-4,13,15,17(17a)-tetraen-3-one
Conditions | Yield |
---|---|
With formic acid at 90℃; for 1h; Heating; | 60% |
methyl 4-azidobenzoate
norethisterone acetate
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 8h; Inert atmosphere; | 60% |
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 8h; Inert atmosphere; | 55% |
norethisterone acetate
2-azido-benzoic acid methyl ester
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 8h; Inert atmosphere; | 50% |
2-azidobenzoic acid
norethisterone acetate
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 8h; Inert atmosphere; | 45% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 10h; Sonogashira coupling; Inert atmosphere; Reflux; | 43% |
norethisterone acetate
N-bromoacetamide
17-acetoxy-19-nor-17βH-pregn-4-ene-3,20-dione
Conditions | Yield |
---|---|
With tert-butyl alcohol und Erwaermen des Reaktionsprodukts mit Zink, Essigsaeure und Natriumacetat; |
Conditions | Yield |
---|---|
(i) HC(OEt)3, TsOH, EtOH, THF, (ii) /BRN= 1730975/, benzene; Multistep reaction; |
Conditions | Yield |
---|---|
(i) HC(OEt)3, TsOH, EtOH, THF, (ii) /BRN= 1731686/, benzene; Multistep reaction; |
Conditions | Yield |
---|---|
(i) HC(OEt)3, TsOH, EtOH, THF, (ii) /BRN= 1900556/, benzene; Multistep reaction; |
norethisterone acetate
Conditions | Yield |
---|---|
(i) MeNH2, MeOH, (ii) aq. Ca(OCl)2, NH3, OTs; Multistep reaction; |
norethisterone acetate
trichloroacetic acid anhydride
17β-Acetoxy-17α-ethinyl-3-trichloracetoxy-Δ3.5-oestradien
chloroform
norethisterone acetate
17α-Aethinyl-6-formyl-3-chlor-19-nor-Δ3.5-androstadien-17β-ol-acetat
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide; trichlorophosphate In Trichloroethylene |
norethisterone acetate
17α-Ethinyl-3-chlor-19-nor-Δ3,5-androstadien-17β-ol-acetat
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide; trichlorophosphate In chloroform; Trichloroethylene |
norethisterone acetate
21-hydroxy-19-norpregna-4,16-diene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent / O2 / K2[PdBr4] / H2O; 1,2-dimethoxy-ethane / 3 h / 65 °C 2: 80 percent / DBU / ethyl acetate / 60 °C 3: 85 percent / K2CO3; water / methanol; tetrahydrofuran / 0.25 h / 20 °C View Scheme |
norethisterone acetate
16α,17α,21-trihydroxy-19-norpregn-4-ene-3,20-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 80 percent / O2 / K2[PdBr4] / H2O; 1,2-dimethoxy-ethane / 3 h / 65 °C 2: 80 percent / DBU / ethyl acetate / 60 °C 3: 85 percent / K2CO3; water / methanol; tetrahydrofuran / 0.25 h / 20 °C 4: 55 percent / OsO4 / pyridine View Scheme | |
Multi-step reaction with 4 steps 1: 80 percent / O2 / K2[PdBr4] / H2O; 1,2-dimethoxy-ethane / 3 h / 65 °C 2: 80 percent / DBU / ethyl acetate / 60 °C 3: 85 percent / formic acid; KMnO4 / acetone; H2O / 0 °C 4: 84 percent / K2CO3; water / methanol; tetrahydrofuran / 0.25 h / 20 °C View Scheme |
norethisterone acetate
3,20-dioxo-19-norpregna-4,16-dien-21-yl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / O2 / K2[PdBr4] / H2O; 1,2-dimethoxy-ethane / 3 h / 65 °C 2: 80 percent / DBU / ethyl acetate / 60 °C View Scheme | |
Multi-step reaction with 3 steps 1: 96 percent / N-bromoacetamide, water / 2-methyl-propan-2-ol / 4 h / Ambient temperature 2: 98 percent / trimethyl phosphite / nitromethane / 1 h / Ambient temperature 3: 63 percent / dimethylformamide / 2 h / 120 °C View Scheme |
IARC Cancer Review: Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 (1979),p. 441.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 (1974),p. 179.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.
1. Introduction of 19-Norethindrone acetate
19-Norethindrone acetate is one kind of white or almost white crystalline. The IUPAC name of this chemical is [(8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate. We can also call it "Norethindrone Acetate". It belongs to Active Pharmaceutical Ingredients;Acetylenes;Biochemistry;Functionalized Acetylenes;Hydroxyketosteroids;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;Steroid and Hormone. Solubility: Insoluble in cold water, hot water. Besides, it should be stored in a closed cool and dry place.
2. Properties of 19-Norethindrone acetate
Physical properties about 19-Norethindrone acetate are:
(1)ACD/LogP: 3.99; (2)ACD/LogD (pH 5.5): 3.99; (3)ACD/LogD (pH 7.4): 3.99; (4)ACD/BCF (pH 5.5): 632.47; (5)ACD/BCF (pH 7.4): 632.47; (6)ACD/KOC (pH 5.5): 3520.35; (7)ACD/KOC (pH 7.4): 3520.35; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 43.37 Å2; (11)Index of Refraction: 1.555; (12)Molar Refractivity: 95.13 cm3; (13)Molar Volume: 296.1 cm3; (14)Polarizability: 37.71×10-24cm3; (15)Surface Tension: 46.1 dyne/cm; (16)Density: 1.14 g/cm3; (17)Flash Point: 197.1 °C; (18)Enthalpy of Vaporization: 71.43 kJ/mol; (19)Boiling Point: 454.7 °C at 760 mmHg; (20)Vapour Pressure: 1.87E-08 mmHg at 25°C.
3. Structure Descriptors of 19-Norethindrone acetate
(1)SMILES: O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)OC(=O)C)[C@@H]2CC3)C)CC4
(2)InChI: InChI=1/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1
(3)InChIKey: IMONTRJLAWHYGT-ZCPXKWAGBE
(4)Std. InChI: InChI=1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1
(5)Std. InChIKey: IMONTRJLAWHYGT-ZCPXKWAGSA-N
4. Physical Properties of 19-Norethindrone acetate
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 161.5 | deg C | EXP | |
log P (octanol-water) | 3.990 | (none) | EST | |
Water Solubility | 5.35 | mg/L | 25 | EXP |
Atmospheric OH Rate Constant | 1.10E-10 | cm3/molecule-sec | 25 | EST |
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