7,17-Dioxoandrost-5-en-3-yl acetate

Base Information

• Chemical Name: 7,17-Dioxoandrost-5-en-3-yl acetate
• CAS No.: 1449-61-2
• Molecular Formula: C21H28O4
• Molecular Weight: 344.451
• European Community (EC) Number: 683-490-4
• NSC Number: 134911
• DSSTox Substance ID: DTXSID70932445
• Mol file: 1449-61-2.mol

Synonyms:7,17-Dioxoandrost-5-en-3-yl acetate;1449-61-2;Androst-5-en-3-ol-7,17-dione acetate;(10,13-dimethyl-7,17-dioxo-2,3,4,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-yl) acetate;NSC134911;7-Oxo-DHEA acetate;DTXSID70932445;AKOS004903478;PD063420;FT-0633552

Chemical Property of 7,17-Dioxoandrost-5-en-3-yl acetate

Chemical Property:

• Vapor Pressure: 2.32E-09mmHg at 25°C
• Melting Point: 184.5-187.5 °C
• Refractive Index: 1.548
• Boiling Point: 479.638 °C at 760 mmHg
• Flash Point: 209.21 °C
• PSA: 60.44000
• Density: 1.18 g/cm³
• LogP: 3.62900
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 344.19875937
• Heavy Atom Count: 25
• Complexity: 677

Purity/Quality:

99% ^*data from raw suppliers

7-KetoNaturalean ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCC2(C3CCC4(C(C3C(=O)C=C2C1)CCC4=O)C)C

Technology Process of 7,17-Dioxoandrost-5-en-3-yl acetate

There total 25 articles about 7,17-Dioxoandrost-5-en-3-yl acetate 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: 96.0%

5-androstene-3β-ol-7,17-dione (566-19-8) + acetic anhydride (108-24-7) → 3-O-acetyl-7-oxo-dehydroepiandrosterone (1449-61-2)

Guidance literature:

With toluene-4-sulfonic acid; for 0.0333333h; microwave irradiation;

DOI:10.1016/S0040-4020(03)00207-2

Reference yield: 93.7%

prasterone acetate (853-23-6) → 3-O-acetyl-7-oxo-dehydroepiandrosterone (1449-61-2)

Guidance literature:

With N-hydroxyphthalimide; sodium dichromate; chromium(III) perchlorate; In water; acetonitrile; at 20 ℃; for 48h; Product distribution / selectivity;

Reference yield: 91.0%

3β-acetoxy-5-androsten-17-one (853-23-6,5223-99-4,18462-31-2,33203-18-8,33855-01-5,104597-49-1) → 3β-acetoxy-androst-5-en-7,17-dione (1449-61-2)

Guidance literature:

With tert.-butylhydroperoxide; copper(l) iodide; In acetonitrile; at 5 - 50 ℃; for 22h;

upstream raw materials:

3β-acetoxy-5-androsten-17-one

prasterone acetate

3β-acetoxy-17-picolinylidene-androst-5-ene

3β-acetoxy-7α-azidoandrost-5-en-17-one

Downstream raw materials:

5α-Androstan-3,7,17-trion

Acetic acid (3S,8R,9S,10R,13S,14S,16R)-10,13-dimethyl-7,17-dioxo-16-phenylselanyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

3β-acetoxy-17a-oxo-androst-5-ene-7,17-dione

3-O-acetyl-7α-OH-DHEA

Refernces

• 1、 Salvador,E Melo,Campos Neves. "Copper-catalysed allylic oxidation of Δ5-steroids by t-butyl hydroperoxide". . p. 119 - 122. Retrieved 1997.
• 2、 Wang, Yi,Kuang, Yi,Zhang, Hongyang,Ma, Ruocheng,Wang, Yuanhua. "Recyclable Dirhodium(II) Catalyst Rh2(esp)2 for the Allylic Oxidation of Δ5-Steroids". . p. 4729 - 4736. Retrieved 2017.
• 3、 ?wizdor, Alina,Panek, Anna,Milecka-Tronina, Natalia. "Biohydroxylation of 7-oxo-DHEA, a natural metabolite of DHEA, resulting in formation of new metabolites of potential pharmaceutical interest". . p. 844 - 849. Retrieved 2016.
• 4、 Zhao, Qian,Qian, Chao,Chen, Xin-Zhi. "N-Hydroxyphthalimide catalyzed allylic oxidation of steroids with t-butyl hydroperoxide". . p. 1 - 6. Retrieved 2015.
• 5、 Li, Jide,Tang, Weiping,Ren, Demin,Xu, Jiaxi,Yang, Zhanhui. "Iridium-catalysed highly selective reduction-elimination of steroidal 4-en-3-ones to 3,5-dienes in water". supporting information. p. 2088 - 2094. Retrieved 2019/04/29.