Methyl 3,17-Dioxo-4-androsten-19-oate

Base Information

• Chemical Name: Methyl 3,17-Dioxo-4-androsten-19-oate
• CAS No.: 22256-03-7
• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.424
• DSSTox Substance ID: DTXSID10559953
• Nikkaji Number: J1.262.968K
• Wikidata: Q82442852
• Mol file: 22256-03-7.mol

Synonyms:22256-03-7;Methyl 3,17-Dioxo-4-androsten-19-oate;Methyl 3,17-dioxoandrost-4-en-19-oate;methyl (8S,9S,10S,13S,14S)-13-methyl-3,17-dioxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-10-carboxylate;Androst-4-en-19-oicacid, 3,17-dioxo-, methyl ester (6CI,7CI,8CI,9CI);DTXSID10559953;AKOS030241203;methyl (8S, 9S, 10S, 13S, 14S)-13-methyl-3, 17-dioxo-2, 6, 7, 8, 9, 11, 12, 14, 15, 16-decahydro-1H-cyclopenta[a]phenanthrene-10-carboxylate

Chemical Property of Methyl 3,17-Dioxo-4-androsten-19-oate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.554
• Boiling Point: 474.829°C at 760 mmHg
• Flash Point: 208.236°C
• PSA: 60.44000
• Density: 1.201g/cm³
• LogP: 3.24050
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 330.18310931
• Heavy Atom Count: 24
• Complexity: 648

Purity/Quality:

97% ^*data from raw suppliers

METHYL 3,17-DIOXO-4-ANDROSTEN-19-OATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CCC4=CC(=O)CCC34C(=O)OC
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=O)CC[C@]34C(=O)OC
• Uses: A methoxy hydroperoxide androstenedione derivative; analog of a potential aromatase intermediate

Technology Process of Methyl 3,17-Dioxo-4-androsten-19-oate

There total 8 articles about Methyl 3,17-Dioxo-4-androsten-19-oate 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: 89.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + androst-4-ene-3,17-dion-19-oic acid (4757-95-3) → 4-Androsten-19-oic-3,17-dione methyl ester (22256-03-7)

Guidance literature:

In diethyl ether;

DOI:10.1016/S0039-128X(99)00108-7

Reference yield: 12.0%

10β-(Z- and E-2-methoxyethylene)estr-4-ene-3,17-dione (111099-43-5,111099-44-6) → 4-Androsten-19-oic-3,17-dione methyl ester (22256-03-7) + (4R,5R,9S,10S,13S,14S)-13-Methyl-3,17-dioxo-tetradecahydro-20-oxa-cyclopropa[4,5]cyclopenta[a]phenanthrene-10-carbaldehyde

Guidance literature:

With pyridine; methanol; (AcO)2O; ozone; Yield given. Multistep reaction;

DOI:10.1039/c39860001651

Reference yield:

19-oxoandrostenedione (968-49-0) → 4-Androsten-19-oic-3,17-dione methyl ester (22256-03-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Fe(III)PFP(Cl), mCPBA / CH₂Cl₂ / 0.33 h / -78 °C

2: 0 °C

With Fe(III)PFP(Cl); 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ja00202a073

upstream raw materials:

diazomethane

androst-4-ene-3,17-dion-19-oic acid

(8R,9S,10S,13S,14S)-10-(Hydroperoxy-methoxy-methyl)-13-methyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione

10β-(Z- and E-2-methoxyethylene)estr-4-ene-3,17-dione

Refernces

• 1、 Templeton, John F.,Majgier-Baranowska, Helena,Marat, Kirk. "Steroid dimer formation: Metal reduction of methyl androst-4-ene-3,17-dion-19-oate". . p. 219 - 223. Retrieved 2000.
• 2、 Watanabe, Yoshihito,Ishimura, Yuzuru. "A Model Study on Aromatase Cytochrome P-450 Reaction: Transformation of Androstene-3,17,19-trione to 10β-Hydroxyestr-4-ene-3,17-dione". . p. 8047 - 8049. Retrieved 2007/10/02.