3,20-Dioxopregna-1,4,9(11),16-tetraen-21-yl acetate

Base Information

• Chemical Name: 3,20-Dioxopregna-1,4,9(11),16-tetraen-21-yl acetate
• CAS No.: 37413-91-5
• Molecular Formula: C23H26O4
• Molecular Weight: 366.457
• European Community (EC) Number: 253-497-3
• DSSTox Substance ID: DTXSID60190855
• Nikkaji Number: J260.764F
• Wikidata: Q72472882
• ChEMBL ID: CHEMBL2348787
• Mol file: 37413-91-5.mol

Synonyms:1,4,9(11),16-Pregnatetraene-21-ol-3,20-Dione-21-Acetate(3TR);Pregna-1,4,9(11),16-tetraene-3,20-dione,21-hydroxy-, acetate (6CI,7CI);21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione;Tetraene Acetate;

Chemical Property of 3,20-Dioxopregna-1,4,9(11),16-tetraen-21-yl acetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 173-175°C
• Refractive Index: 1.585
• Boiling Point: 534.568 °C at 760 mmHg
• Flash Point: 233.008 °C
• PSA: 60.44000
• Density: 1.211 g/cm³
• LogP: 3.88290
• Storage Temp.: Refrigerator
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 366.18310931
• Heavy Atom Count: 27
• Complexity: 856

Purity/Quality:

98% ^*data from raw suppliers

21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C1=CCC2C1(CC=C3C2CCC4=CC(=O)C=CC43C)C
• Isomeric SMILES: CC(=O)OCC(=O)C1=CC[C@@H]2[C@@]1(CC=C3[C@H]2CCC4=CC(=O)C=C[C@@]43C)C

Technology Process of 3,20-Dioxopregna-1,4,9(11),16-tetraen-21-yl acetate

There total 22 articles about 3,20-Dioxopregna-1,4,9(11),16-tetraen-21-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: 98.8%

pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (4380-55-6) → 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (37413-91-5)

Guidance literature:

pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate; With pyridine; N-chloro-succinimide; at -15 ℃; for 1h; Inert atmosphere;

With sulfur dioxide; at -10 ℃; for 0.5h; Inert atmosphere;

Reference yield: 83.5%

prednisolone 21-acetate (52-21-1) → 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (37413-91-5)

Guidance literature:

prednisolone 21-acetate; With pyridine; N-chloro-succinimide; at -15 - 20 ℃; for 0.416667h; Inert atmosphere;

With sulfur dioxide; for 1h; Inert atmosphere;

Reference yield: 61.0%

21-Acetoxypregna-4,9(11),16-trien-3,20-dion (23460-76-6) → 21-Acetoxy-1,4,9(11),16-pregnatetraen-3,20-dion (37413-91-5)

Guidance literature:

With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; at 100 ℃; for 6h;

upstream raw materials:

Androstadien-(4,9,⁽¹¹⁾)-dion-3,17

21-Acetoxypregna-4,9⁽¹¹⁾,16-trien-3,20-dion

21-acetoxy-pregna-4,9⁽¹¹⁾,16-triene-3,20-dinone

2,4,6-trimethyl-pyridine

Downstream raw materials:

16α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione-21-acetate

2-oxo-2-((8S,10S,13S,14S,16R,17S)-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)ethyl acetate

17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate

triamcinolone acetonide

Refernces

• 1、 Huy, Luu D.,Diep, Nguyen T.,Vu, Tran K.,Savinova, Tatiana S.,Donova, Marina V.. "An efficient procedure for the synthesis of 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione". . p. 225 - 231. Retrieved 2020/04/27.
• 2、 -. "Method for preparing tetraene acetate". Paragraph 0021-0023; 0026; 0029; 0032; 0035; 0038. . Retrieved 2019/01/07.