D-13β-ethyl-17β-hydroxy-3-methoxy-gona-2,5(10)-diene
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
Conditions | Yield |
---|---|
With sulfur trioxide pyridine complex In dimethyl sulfoxide; triethylamine Ambient temperature; | 85% |
With molecular sieve; aluminum isopropoxide; butanone In benzene for 12h; Heating; | 84% |
83% |
18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / NH3 liq., Li / propan-2-ol; tetrahydrofuran / -45 °C 2: 85 percent / Py*SO3 / dimethylsulfoxide; triethylamine / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: (i) LiNH2, liq. NH3, PhNH2, THF, (ii) AcOH, EtOH 2: Al(OiPr)3 / butan-2-one; benzene / Heating View Scheme | |
Multi-step reaction with 3 steps 1: ammonium chloride; ammonia / tetrahydrofuran; water; aniline 2: ammonia; lithium / tetrahydrofuran; ethanol; water View Scheme | |
Multi-step reaction with 3 steps 1: ammonium chloride; ammonia / tetrahydrofuran; water; aniline 2: ammonia; lithium / tetrahydrofuran; ethanol; water 3: water; cyclohexanone; toluene View Scheme |
2-Trimethylsilyl-1-(4-methoxy-2-methylphenyl)-2-propen-1-on
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) 80 percent NaH; 2.) 10 percent H2SO4 / 1.) DME, parrafin oil, 3.5 h, reflux; Et2O, -20 deg C, 30 min; 2.) MeOH, 24 h 3: 84 percent / mol. sieve, 2-butanone, aluminium isopropylate / benzene / 12 h / Heating View Scheme |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) 80 percent NaH; 2.) 10 percent H2SO4 / 1.) DME, parrafin oil, 3.5 h, reflux; Et2O, -20 deg C, 30 min; 2.) MeOH, 24 h 3: 84 percent / mol. sieve, 2-butanone, aluminium isopropylate / benzene / 12 h / Heating View Scheme |
13-Ethyl-3-methoxy-6,7:8,9-disecogona-1,3,5(10),7-tetraen-9,17-dion
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 84 percent / mol. sieve, 2-butanone, aluminium isopropylate / benzene / 12 h / Heating View Scheme |
13β-Aethyl-3-methoxy-gonapentaen-(1.3.5(10).8.14)-ol-(17β)-acetat
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: H2 / Pd-CaCO3 / benzene; tetrahydrofuran 2: KOH / methanol 3: (i) LiNH2, liq. NH3, PhNH2, THF, (ii) AcOH, EtOH 4: Al(OiPr)3 / butan-2-one; benzene / Heating View Scheme |
13β-ethyl-3-methoxygona-1,3,5(10)8-tetraen-17β-yl acetate
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: KOH / methanol 2: (i) LiNH2, liq. NH3, PhNH2, THF, (ii) AcOH, EtOH 3: Al(OiPr)3 / butan-2-one; benzene / Heating View Scheme |
D-13β-ethyl-17β-hydroxy-3-methoxy-gona-2,5(10)-diene
aluminum isopropoxide
sodium sulfate
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
Conditions | Yield |
---|---|
In water; cyclohexanone; toluene | |
In water; cyclohexanone; toluene |
(+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ammonia; lithium / tetrahydrofuran; ethanol; water View Scheme | |
Multi-step reaction with 2 steps 1: ammonia; lithium / tetrahydrofuran; ethanol; water 2: water; cyclohexanone; toluene View Scheme |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
DL-13β-ethyl-gon-5(10)-ene-3,17-dione
Conditions | Yield |
---|---|
With oxalic acid; silica gel In methanol; dichloromethane; water for 0.25h; Ambient temperature; | 92% |
With oxalic acid In dichloromethane; water for 0.333333h; Ambient temperature; | 87% |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
trimethylsilylacetylene
levonorgestrel
Conditions | Yield |
---|---|
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -40 - -20℃; for 1h; Inert atmosphere; Stage #2: 13β-ethyl-3-methoxygona-2,5(10)-diene-17-one In tetrahydrofuran; hexane at -40℃; for 1h; Inert atmosphere; Further stages; | 90% |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
ethylene glycol
13β-ethyl-3-methoxy-17,17-ethylenedioxy-gona-2,5(10)-diene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; orthoformic acid triethyl ester at 40℃; | 80% |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
acetylene
13β-ethyl-3-methoxy-17α-ethynyl-gona-2,5(10)-dien-17β-ol
Conditions | Yield |
---|---|
Stage #1: acetylene With potassium tert-butylate In tetrahydrofuran at -10 - 15℃; for 1h; Inert atmosphere; Stage #2: 13β-ethyl-3-methoxygona-2,5(10)-diene-17-one In tetrahydrofuran at -10 - 0℃; for 3h; | 75% |
(i) Li, H2NCH2CH2NH2, THF, (ii) aq. H2S; Multistep reaction; | |
Stage #1: 13β-ethyl-3-methoxygona-2,5(10)-diene-17-one; acetylene With potassium tert-butylate In tetrahydrofuran at -10 - 0℃; for 4h; Inert atmosphere; Stage #2: With sulfuric acid In tetrahydrofuran; water pH=5 - 6; |
Conditions | Yield |
---|---|
(i) Li, H2NCH2CH2NH2, THF, (ii) aq. HCl, MeOH; Multistep reaction; | |
With hydrogenchloride; lithium diisopropyl amide 1.) THF, 2.5 h; 2.) MeOH, 60-70 deg C, 3 h; Yield given. Multistep reaction; | |
With hydrogenchloride; lithium 1.) ethylenediamine, 1 h; 2.) THF, r.t., 2 h; 3.) MeOH, 45-50 degC, 45 min; Yield given. Multistep reaction; |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / HC(OEt)3, p-TsOH / 40 °C 2: 51 percent / oxalic acid, silica gel / CH2Cl2; methanol; H2O / 0.25 h / Ambient temperature View Scheme |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
DL-13β-ethyl-gona-4,9-diene-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 87 percent / oxalic acid on silica gel / CH2Cl2; H2O / 0.33 h / Ambient temperature 2: 57 percent / pyridinium bromide perbromide / pyridine / Ambient temperature View Scheme |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
(8S,13S,14S)-13-Ethyl-1,4,6,7,8,12,13,14,15,16-decahydro-2H-cyclopenta[a]phenanthrene-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 87 percent / oxalic acid on silica gel / CH2Cl2; H2O / 0.33 h / Ambient temperature 2: 57 percent / pyridinium bromide perbromide / pyridine / Ambient temperature 3: 95 percent / methanol / 2.5 h / 69 °C 4: 86percent HCOOH / 0.17 h / Ambient temperature View Scheme |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 87 percent / oxalic acid on silica gel / CH2Cl2; H2O / 0.33 h / Ambient temperature 2: 57 percent / pyridinium bromide perbromide / pyridine / Ambient temperature 3: 95 percent / methanol / 2.5 h / 69 °C 4: 86percent HCOOH / 0.17 h / Ambient temperature 5: O2, Et3N / methanol / 52 h / Ambient temperature 6: 80 percent / NaI, AcOH / methanol / 8 h / Ambient temperature 7: 45 percent / H2, pyridine / 5percent Pd/SrCO3 / 2 h / Ambient temperature View Scheme |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
DL-13β-ethyl-11β-hydroxy-gona-4,9-dien-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 87 percent / oxalic acid on silica gel / CH2Cl2; H2O / 0.33 h / Ambient temperature 2: 57 percent / pyridinium bromide perbromide / pyridine / Ambient temperature 3: 95 percent / methanol / 2.5 h / 69 °C 4: 86percent HCOOH / 0.17 h / Ambient temperature 5: O2, Et3N / methanol / 52 h / Ambient temperature 6: 80 percent / NaI, AcOH / methanol / 8 h / Ambient temperature View Scheme |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
(8S,11S,13S,14S)-13-Ethyl-11-hydroperoxy-1,6,7,8,11,12,13,14,15,16-decahydro-2H-cyclopenta[a]phenanthrene-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 87 percent / oxalic acid on silica gel / CH2Cl2; H2O / 0.33 h / Ambient temperature 2: 57 percent / pyridinium bromide perbromide / pyridine / Ambient temperature 3: 95 percent / methanol / 2.5 h / 69 °C 4: 86percent HCOOH / 0.17 h / Ambient temperature 5: O2, Et3N / methanol / 52 h / Ambient temperature View Scheme |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 87 percent / oxalic acid on silica gel / CH2Cl2; H2O / 0.33 h / Ambient temperature 2: 57 percent / pyridinium bromide perbromide / pyridine / Ambient temperature 3: 95 percent / methanol / 2.5 h / 69 °C View Scheme |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
D-17β-acetoxy-13β-ethyl-17α-ethynyl-gon-4-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) Li, H2NCH2CH2NH2, THF, (ii) aq. HCl, MeOH 2: collidine / Heating View Scheme | |
Multi-step reaction with 4 steps 1: tetrahydrofuran; water 2: hydrogenchloride / methanol; water; ethyl acetate; benzene 3: pyridine; acetic anhydride 4: hydrogenchloride; potassium hydroxide; sodium hydrogencarbonate / tetrahydrofuran; methanol View Scheme |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
dl-13-ethyl-17α-ethynyl-3,17-dihydroxygona-3,5-diene, diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) Li, H2NCH2CH2NH2, THF, (ii) aq. HCl, MeOH 2: Py / 160 °C View Scheme | |
Multi-step reaction with 3 steps 1: tetrahydrofuran; water 2: hydrogenchloride / methanol; water; ethyl acetate; benzene 3: pyridine; acetic anhydride View Scheme |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
magnesium sulfate
13β-ethyl-3-methoxy-17α-ethynyl-gona-2,5(10)-dien-17β-ol
Conditions | Yield |
---|---|
In tetrahydrofuran; water |
ethyl bromide
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
1-propynylmagnesium bromide
13β-ethyl-3-methoxy-17α-propynyl-gona-2,5(10)-dien-17β-ol
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran; methanol; water | |
With magnesium In tetrahydrofuran; methanol; water |
1,1-Dichloroethylene
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
lithium chloroacetylide
17α-chloroethynyl-13-ethyl-3-methoxygona-2,5(10)-dien-17β-ol
Conditions | Yield |
---|---|
With methyllithium In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate | |
With methyllithium In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
13β-ethyl-gon-4-en-3,17-dione
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydrogencarbonate In methanol; water; ethyl acetate | |
With hydrogenchloride; sodium hydrogencarbonate In methanol; water; ethyl acetate |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
13β-ethyl-3-methoxy-17α-ethynyl-gona-2,5(10)-dien-17β-ol
Conditions | Yield |
---|---|
In tetrahydrofuran; water |
13β-ethyl-3-methoxygona-2,5(10)-diene-17-one
13β-Ethyl-3-methoxy-17α-allyl-gona-2,5(10)-dien-17β-ol
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran; methanol; water; allyl bromide | |
With magnesium In tetrahydrofuran; methanol; water; allyl bromide | |
With magnesium In tetrahydrofuran; methanol; water; allyl bromide |
The Gona-2,5(10)-dien-17-one,13-ethyl-3-methoxy-, with the cas registry number 2322-77-2, has the IUPAC name of (8R,9S,13S,14S)-13-ethyl-3-methoxy-4,6,7,8,9,11,12,14,15,
16-decahydro-1H-cyclopenta[a]phenanthren-17-one. This is a kind of crystal compound and is usually used as the intermediate of 18-methylnorethindrone and ethyl norgestrienonum.
The physical properties of this chemical are as follows: (1)ACD/LogP: 4.31; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.31; (4)ACD/LogD (pH 7.4): 4.31; (5)ACD/BCF (pH 5.5): 1119.35; (6)ACD/BCF (pH 7.4): 1119.35; (7)ACD/KOC (pH 5.5): 5297.24; (8)ACD/KOC (pH 7.4): 5297.24; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 26.3; (13)Index of Refraction: 1.551; (14)Molar Refractivity: 87.41 cm3; (15)Molar Volume: 273.9 cm3; (16)Polarizability: 34.65 ×10-24 cm3; (17)Surface Tension: 40.9 dyne/cm; (18)Density: 1.09 g/cm3; (19)Flash Point: 188.8 °C; (20)Enthalpy of Vaporization: 70.65 kJ/mol; (21)Boiling Point: 448 °C at 760 mmHg; (22)Vapour Pressure: 3.21E-08 mmHg at 25°C; (23)Exact Mass: 300.20893; (24)MonoIsotopic Mass: 300.20893; (25)Topological Polar Surface Area: 26.3; (26)Heavy Atom Count: 22; (27)Formal Charge: 0; (28)Complexity: 556.
The production method is as below: Firstly, deoxidate 3-methoxy-18-methyl-1,3,5 (10) and 8-estragonatetren-17-one with potassium borohydrate to produce 3-methoxy-18-methyl2,5(10)estragonadien-17-ol; Secondly oxidate it with cyclohexanone-isopropanol aluminium, and then you could obtain this chemical.
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CCC12CCC3C(C1CCC2=O)CCC4=C3CC=C(C4)OC
(2)Isomeric SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3CC=C(C4)OC
(3)InChI: InChI=1S/C20H28O2/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/h5,16-18H,3-4,6-12H2,1-2H3/t16-,17-,18+,20+/m1/s1
(4)InChIKey: PQMRKLSVUBRLLQ-XSYGEPLQSA-N
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