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95716-70-4

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Basic Information
CAS No.: 95716-70-4
Name: (7a,17a)-17-Hydroxy-3-oxo-pregna-4,9(11)-diene-7,21-dicarboxylicacid g-lactone methyl ester
Article Data: 13
Molecular Structure:
Molecular Structure of 95716-70-4 ((7a,17a)-17-Hydroxy-3-oxo-pregna-4,9(11)-diene-7,21-dicarboxylicacid g-lactone methyl ester)
Formula: C24H30O5
Molecular Weight: 398.499
Synonyms: 7a-(Methoxycarbonyl)-9(11)D-canrenone;D9,11-Eplerenone;
Density: 1.24 g/cm3
Boiling Point: 580.2 °C at 760 mmHg
Flash Point: 251.7 °C
PSA: 69.67000
LogP: 3.91330
Related products
Synthetic route

17α-pregna-4-ene-7α,21-dicarboxylic acid-11α,17β-dihydroxy-3-oxo-γ-lactone-7-methyl ester

95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

Conditions
ConditionsYield
With phosphorus pentachloride; boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.166667h; Reagent/catalyst; Temperature;90.9%
192704-56-6

11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

Conditions
ConditionsYield
With hexafluoropropene-diethylamine adduct; diethyl-(pentafluoro-propenyl)-amine In chloroform at 30℃; for 30h; Solvent; Temperature; Reagent/catalyst;90%
Stage #1: 11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone With methanesulfonyl chloride; triethylamine In dichloromethane at 5℃; for 1h;
Stage #2: With formic acid; potassium formate; acetic anhydride at 70 - 95℃; for 5 - 9h;		77%
With 1H-imidazole; sulfuryl dichloride In tetrahydrofuran at -10 - 20℃; for 1.5h;71%
192704-58-8

methyl hydrogen 17α-hydroxy-11α-(methylsulfonyl)oxy-3-oxopregn-4-ene-7α,21-dicarboxylate, γ-lactone

95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

Conditions
ConditionsYield
With formic acid; potassium formate; acetic anhydride at 70 - 100℃; for 19h; Inert atmosphere;80%
With formic acid; potassium formate; acetic anhydride at 70 - 105℃; for 6.5h;1.9 g
Stage #1: methyl hydrogen 17α-hydroxy-11α-(methylsulfonyl)oxy-3-oxopregn-4-ene-7α,21-dicarboxylate, γ-lactone With Isopropenyl acetate; toluene-4-sulfonic acid at 90℃; for 5h;
Stage #2: With sodium acetate; acetic acid at 100℃; for 1h;		0.4 g
192704-56-6

11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

A

3-oxo-17α-pregn-4-ene-7α,9:21,17-dicarbolactone

B

192704-70-4

7-methyl hydrogen 17α-hydroxy-3-oxopregna-4,11-diene-7α,21-dicarboxylate, γ-lactone

C

95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

Conditions
ConditionsYield
Stage #1: 11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone With methanesulfonyl chloride; triethylamine In dichloromethane at 0℃; for 1.41667h;
Stage #2: With formic acid; potassium formate; acetic anhydride at 40 - 95℃; for 2h;		A 2.27 g
B 3.72 g
C 68.8%
Stage #1: 11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone With sulfuryl dichloride In tetrahydrofuran at -70℃; for 0.5h;
Stage #2: With 1H-imidazole In tetrahydrofuran at -70 - 20℃; for 2h;
Stage #1: 11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone With methanesulfonyl chloride; triethylamine In dichloromethane at -5 - 0℃; for 1.33333h;
Stage #2: With sodium acetate; acetic anhydride; acetic acid In dichloromethane at 55 - 135℃; for 1.5 - 2h;
...Expand
67-56-1

methanol

7a-(1,4-dicarbonylpentenyl)-9(11)-encanrenone

95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

Conditions
ConditionsYield
With ozone at -50℃;49.31%
186581-53-3, 908094-01-9

diazomethane

95716-74-8

17β-hydroxypregna-4,9(11)-dien-3-one-7α,21-dicarboxylic acid γ-lactone

95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

Conditions
ConditionsYield
In diethyl ether; dichloromethane for 0.166667h;2.7 g
77-78-1

dimethyl sulfate

95716-74-8

17β-hydroxypregna-4,9(11)-dien-3-one-7α,21-dicarboxylic acid γ-lactone

95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

Conditions
ConditionsYield
In water; acetone at 45℃; for 3h;50.94 g
With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate In dichloromethane; water at 20 - 25℃; for 11.5h;
Stage #1: dimethyl sulfate; 17β-hydroxypregna-4,9(11)-dien-3-one-7α,21-dicarboxylic acid γ-lactone In water; acetone at 45℃; for 3h;
Stage #2: With potassium hydrogencarbonate; triethylamine In water; acetone at 45℃; for 1h;
610785-40-5

17β-hydroxy-7α-(5'-methyl-2'-furyl)-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone

95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium acetate; dibromantin / acetone; H2O / -10 °C
2.1: aq. HCl / CH2Cl2 / 2.5 h / 20 °C
3.1: O3/O2 / CH2Cl2; propan-2-ol / 0.17 h / -55 °C
3.2: dimethylsilfide / CH2Cl2; propan-2-ol / 0.83 h / 20 °C
4.1: 0.865 mg / H2O2; KHCO3 / H2O; methanol / 16 h / 20 °C
5.1: 50.94 g / acetone; H2O / 3 h / 45 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium acetate; dibromantin / acetone; H2O / -10 °C
2.1: O3/O2; H2O / CH2Cl2; propan-2-ol / 0.04 h / -55 °C
2.2: dimethylsilfide / CH2Cl2; propan-2-ol / 0.75 h / 20 °C
2.3: 86.1 percent / H2O2; KHCO3 / H2O; methanol / 15 h / 20 °C
3.1: 50.94 g / acetone; H2O / 3 h / 45 °C
View Scheme
Multi-step reaction with 5 steps
1.1: O3/O2 / CH2Cl2; methanol / -78 °C
1.2: O2; trimethylphosphite / 1 h / 20 °C
2.1: 1.40 g / aq. HCl / 0.33 h / 20 °C
3.1: O3/O2 / CH2Cl2 / -78 - 20 °C
4.1: H2O2; KHCO3 / H2O / 1.5 h / 20 °C
5.1: 50.94 g / acetone; H2O / 3 h / 45 °C
View Scheme

C25H32O6

95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.865 mg / H2O2; KHCO3 / H2O; methanol / 16 h / 20 °C
2: 50.94 g / acetone; H2O / 3 h / 45 °C
View Scheme
610785-44-9

17β-hydroxy-7α-(2'-hydroperoxy-2'-methoxyacetyl)-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone

95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2O2; KHCO3 / H2O / 1.5 h / 20 °C
2: 50.94 g / acetone; H2O / 3 h / 45 °C
View Scheme
Raw Materials
192569-17-8
192704-56-6
95716-71-5
77-78-1
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  • (7a,17a)-17-Hydroxy-3-oxo-pregna-4,9(11)-diene-7,21-dicarboxylicacid g-lactone methyl ester

  • Casno:

    95716-70-4

    (7a,17a)-17-Hydroxy-3-oxo-pregna-4,9(11)-diene-7,21-dicarboxylicacid g-lactone methyl ester

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Specification

The (7a,17a)-17-Hydroxy-3-oxo-pregna-4,9(11)-diene-7,21-dicarboxylicacid g-lactone methyl ester is an organic compound with the formula C24H30O5. The systematic name of this chemical is methyl (7R,10S,13S,17R)-10,13-dimethyl-3,5'-dioxo-spiro[2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,2'-tetrahydrofuran]-7-carboxylate. With the CAS registry number 95716-70-4, it is also named as Eplerenone Intermediate. The product's category is Intermediate of Eplerenone.

The other characteristics of (7a,17a)-17-Hydroxy-3-oxo-pregna-4,9(11)-diene-7,21-dicarboxylicacid g-lactone methyl ester can be summarized as: (1)ACD/LogP: 2.37; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.37; (4)ACD/LogD (pH 7.4): 2.37; (5)ACD/BCF (pH 5.5): 37.2; (6)ACD/BCF (pH 7.4): 37.2; (7)ACD/KOC (pH 5.5): 463.21; (8)ACD/KOC (pH 7.4): 463.21; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 69.67 Å2; (13)Index of Refraction: 1.576; (14)Molar Refractivity: 106.11 cm3; (15)Molar Volume: 320.6 cm3; (16)Polarizability: 42.06×10-24 cm3; (17)Surface Tension: 49.5 dyne/cm; (18)Density: 1.24 g/cm3; (19)Flash Point: 251.7 °C; (20)Enthalpy of Vaporization: 86.79 kJ/mol; (21)Boiling Point: 580.2 °C at 760 mmHg; (22)Vapour Pressure: 1.87E-13 mmHg at 25°C.

People can use the following data to convert to the molecule structure. 
1. SMILES:C[C@]12CCC(=O)C=C1C[C@H](C3C2=CC[C@]4(C3CC[C@@]45CCC(=O)O5)C)C(=O)OC
2. InChI:InChI=1/C24H30O5/c1-22-8-4-15(25)12-14(22)13-16(21(27)28-3)20-17(22)5-9-23(2)18(20)6-10-24(23)11-7-19(26)29-24/h5,12,16,18,20H,4,6-11,13H2,1-3H3/t16-,18?,20?,22+,23+,24-/m1/s1
3. InChIKey:GWEKWJOSBYDYDP-CQPWOFQEBB