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2322-77-2

Basic Information
CAS No.: 2322-77-2
Name: Methoxydienone
Article Data: 11
Molecular Structure:
Molecular Structure of 2322-77-2 (Methoxydienone)
Formula: C20H28O2
Molecular Weight: 300.441
Synonyms: METHOXYDIENONE;13-beta-Ethyl-3-methoxygona-2,5(10)-dien-17-one;(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;13-Ethyl-3-methoxy-gona-2,5(10;D(-)-18-METHYL-3-METHOXY-ESTRA-2,5(10)-DIEN-17-ONE;METHOXYDIENONE(13-BETA-ETHYL-3-METHOXYGONA-2,5(10)-DIEN-17-ONE);18-Methylestra-2,5(10)-dien-3-ol-17-one-3-methy ether;3-Methoxy-18-methylestra-2,5(10)-dien-17-one
EINECS: 219-034-4
Density: 1.09 g/cm3
Melting Point: ≥170oC
Boiling Point: 448 °C at 760 mmHg
Flash Point: 188.8 °C
Solubility: 270μg/L at 20℃
Appearance: White to Off-White Crystalline Powder
PSA: 26.30000
LogP: 4.80260
Synthetic route
14507-49-4

D-13β-ethyl-17β-hydroxy-3-methoxy-gona-2,5(10)-diene

2322-77-2

13β-ethyl-3-methoxygona-2,5(10)-diene-17-one

Conditions
ConditionsYield
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%
7443-72-3

18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol

2322-77-2

13β-ethyl-3-methoxygona-2,5(10)-diene-17-one

Conditions
ConditionsYield
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
75863-25-1

2-Trimethylsilyl-1-(4-methoxy-2-methylphenyl)-2-propen-1-on

2322-77-2

13β-ethyl-3-methoxygona-2,5(10)-diene-17-one

Conditions
ConditionsYield
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

(2R)-2-ethyl-3-vinyl-1-cyclopentanon

2322-77-2

13β-ethyl-3-methoxygona-2,5(10)-diene-17-one

Conditions
ConditionsYield
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
101025-85-8

13-Ethyl-3-methoxy-6,7:8,9-disecogona-1,3,5(10),7-tetraen-9,17-dion

2322-77-2

13β-ethyl-3-methoxygona-2,5(10)-diene-17-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 84 percent / mol. sieve, 2-butanone, aluminium isopropylate / benzene / 12 h / Heating
View Scheme
2911-81-1, 5941-86-6, 85760-97-0

13β-Aethyl-3-methoxy-gonapentaen-(1.3.5(10).8.14)-ol-(17β)-acetat

2322-77-2

13β-ethyl-3-methoxygona-2,5(10)-diene-17-one

Conditions
ConditionsYield
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
14507-47-2

13β-ethyl-3-methoxygona-1,3,5(10)8-tetraen-17β-yl acetate

2322-77-2

13β-ethyl-3-methoxygona-2,5(10)-diene-17-one

Conditions
ConditionsYield
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
14507-49-4

D-13β-ethyl-17β-hydroxy-3-methoxy-gona-2,5(10)-diene

555-31-7

aluminum isopropoxide

7757-82-6

sodium sulfate

2322-77-2

13β-ethyl-3-methoxygona-2,5(10)-diene-17-one

Conditions
ConditionsYield
In water; cyclohexanone; toluene
In water; cyclohexanone; toluene
3625-82-9

(+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene

2322-77-2

13β-ethyl-3-methoxygona-2,5(10)-diene-17-one

Conditions
ConditionsYield
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
2322-77-2

13β-ethyl-3-methoxygona-2,5(10)-diene-17-one

4222-96-2

DL-13β-ethyl-gon-5(10)-ene-3,17-dione

Conditions
ConditionsYield
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%
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Specification

 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