Estradiene dione-3-keta

Base Information

• Chemical Name: Estradiene dione-3-keta
• CAS No.: 5571-36-8
• Molecular Formula: C20H26O3
• Molecular Weight: 314.425
• Hs Code.: 2932999099
• European Community (EC) Number: 427-230-8,611-306-4
• UNII: 2RAF5TL6V2
• DSSTox Substance ID: DTXSID30427741
• Nikkaji Number: J675.511I
• Wikidata: Q63395993
• Mol file: 5571-36-8.mol

Synonyms:5571-36-8;Estradiene dione-3-keta;Estra-5(10),9(11)-diene-3,17-dione 3-Ethylene Ketal;(8S,13S,14S)-13-Methyl-1,2,6,7,8,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17(4H)-one;Ethylene deltenone;EC 427-230-8;(8S,13S,14S)-13-methylspiro[1,2,4,6,7,8,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,2'-1,3-dioxolane]-17-one;3,3-(Ethylenedioxy)estra-5(10),9(11)-dien-17-one;cyclic 3-(1,2-ethanediylacetale)-estra-5(10),9(11)-diene-3,17-dione;MFCD08062585;(8S,13S,14S)-13-Methyl-1,4,6,7,8,12,13,14,15,16-decahydrospiro(cyclopenta(a)phenanthrene-3,2'-(1,3)dioxolan)-17(2H)-one;(8S,13S,14S)-13-methyl-1,4,6,7,8,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17(2H)-one;3-Ethylene dioxy-17-oxo estra-5(10), 9(11)-diene;3-Ethylene dioxy-17-oxo-13-methyl estra-5(10)9(11)-diene;2RAF5TL6V2;SCHEMBL1173789;DTXSID30427741;XUOQKQRMICQUQC-AOIWGVFYSA-N;BCP13464;STL556506;AKOS015840140;AKOS016011499;CS-W007969;GS-3157;AC-28722;E0918;A870115;Q-102805;3,3-ethylenedioxyestra-5(10), 9(11)-dien-17-one;3,3-ethylenedioxyestra-5(10),9(11)-diene-17-one;3-Ethylenedioxy-estra-5(10), 9(11)-dien-17-one;Q63395993;3,3-(Ethylenedioxy)estra-5(10),9(11)-diene-17-one;3,3-ethylenedioxy-estra-5(10),9(11)-diene-17-one;3-Ethylene dioxy-17-oxo estra-5 (10), 9(11)-diene;cyclic3-(1,2-ethanediylacetale)-estra-5(10),9(11)-diene-3,17-dione;Estra-5(10),9(11)-diene-3,17-dione, cyclic 3-(1,2-ethanediyl acetal);Spiro[1,3-dioxolan-2,3'-estra-5'(10'),9'(11')-dien]-17'-one;Spiro[1,3-dioxolan-2,3?-estra-5?(10?),9?(11?)-dien]-17?-one;(10'S,11'S,15'S)-15'-methylspiro[1,3-dioxolane-2,5'-tetracyclo[8.7.0.0?,?.0??,??]heptadecane]-1'(17'),2'(7')-dien-14'-one;(10'S,11'S,15'S)-15'-methylspiro[1,3-dioxolane-2,5'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-1'(17'),2'(7')-dien-14'-one

Chemical Property of Estradiene dione-3-keta

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 1.12E-09mmHg at 25°C
• Melting Point: 152-154 °C
• Refractive Index: 1.582
• Boiling Point: 488.1 °C at 760 mmHg
• Flash Point: 241.2 °C
• PSA: 35.53000
• Density: 1.2 g/cm³
• LogP: 3.93550
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Sparingly, Heated, Sonicated), Methanol (Slightly)
• Water Solubility.: 903μg/L at 25℃
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 314.18819469
• Heavy Atom Count: 23
• Complexity: 623

Purity/Quality:

99% ^*data from raw suppliers

Estra-5(10),9(11)-diene-3,17-dione 3-Ethylene Ketal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC=C3C(C1CCC2=O)CCC4=C3CCC5(C4)OCCO5
• Isomeric SMILES: C[C@]12CC=C3[C@H]([C@@H]1CCC2=O)CCC4=C3CCC5(C4)OCCO5
• Uses: Mifepristone intermediate; antiprogestational antiglucocorticoid antagonist steroidal spirooxazole.

Technology Process of Estradiene dione-3-keta

There total 4 articles about Estradiene dione-3-keta which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.3%

(8S,13S,14S,17S)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol (53303-91-6) → ethylene deltenone (5571-36-8)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; for 0.25h; Ambient temperature;

DOI:10.1021/jm00089a024

Reference yield:

17β-hydroxyestra-4,9-dien-3-one (6218-29-7) → ethylene deltenone (5571-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / H₂SO₄ / benzene; CH₂Cl₂ / 2.5 h / Heating

2: 99.3 percent / N-methylmorpholine N-oxide, (nC₃H₇)4NRuO₄ / CH₂Cl₂ / 0.25 h / Ambient temperature

With tetrapropylammonium perruthennate; sulfuric acid; 4-methylmorpholine N-oxide; In dichloromethane; benzene;

DOI:10.1021/jm00089a024

Reference yield:

4,9-Androstadiene-3,17-dione (5173-46-6) → ethylene deltenone (5571-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / tetrahydrofuran; methanol / -10 °C

2: 1.) (EtO)3CH, pTsOH, 2.) pyridinium chlorochromate / 2.) CH₂Cl₂

With sodium tetrahydroborate; toluene-4-sulfonic acid; orthoformic acid triethyl ester; pyridinium chlorochromate; In tetrahydrofuran; methanol;

DOI:10.1016/S0960-894X(97)00397-1

upstream raw materials:

(8S,13S,14S,17S)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol

ethylene glycol

4,9-Androstadiene-3,17-dione

17β-hydroxyestra-4,9-dien-3-one

Downstream raw materials:

(5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one

3,3-(ethylenedioxy)-5β,10β-epoxyestra-9(11)-ene-17-one

11β-[4-(N,N-Dimethylamino)phenyl]-17β-nitroestra-4,9-dien-3-one

C₂₈H₃₂O₃

Refernces

• 1、 Liu,Carlson,Katzenellenbogen. "Synthesis of high affinity fluorine-substituted ligands for the androgen receptor. Potential agents for imaging prostatic cancer by positron emission tomography". . p. 2113 - 2129. Retrieved 2007/10/02.