21-Hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate

Base Information

• Chemical Name: 21-Hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate
• CAS No.: 23460-76-6
• Molecular Formula: C23H28 O4
• Molecular Weight: 368.473
• European Community (EC) Number: 245-674-9
• DSSTox Substance ID: DTXSID20178013
• Nikkaji Number: J228.970I
• Wikidata: Q83048351
• Mol file: 23460-76-6.mol

Synonyms:23460-76-6;21-Hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate;EINECS 245-674-9;SCHEMBL8999936;DTXSID20178013;3,20-Dioxopregna-4,9(11),16-triene-21-ol acetate;21-acetoxypregna-4(5),9(11),16(17)-triene-3,20-dione

Chemical Property of 21-Hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate

Chemical Property:

• Vapor Pressure: 2.65E-11mmHg at 25°C
• Melting Point: 124-125 °C(Solv: acetone (67-64-1); ligroine (8032-32-4))
• Boiling Point: 529.6°Cat760mmHg
• Flash Point: 230.4°C
• PSA: 60.44000
• Density: 1.19g/cm³
• LogP: 4.10690
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 368.19875937
• Heavy Atom Count: 27
• Complexity: 814

Purity/Quality:

99.9% ^*data from raw suppliers

21-Hydroxypregna-4,9(11),16-triene-3,20-dione21-Acetate ^*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)CCC43C)C
• Isomeric SMILES: CC(=O)OCC(=O)C1=CC[C@@H]2[C@@]1(CC=C3[C@H]2CCC4=CC(=O)CC[C@@]43C)C
• Uses: 21-Hydroxypregna-4,9(11),16-triene-3,20-dione 21-Acetate is derived from Hydrocortisone 21-Acetate (Hydrocortisone EP Impurity C) (H714620), which is a glucocorticoid.

Technology Process of 21-Hydroxypregna-4,9(11),16-triene-3,20-dione 21-acetate

There total 17 articles about 21-Hydroxypregna-4,9(11),16-triene-3,20-dione 21-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: 99.0%

anecortave (7753-60-8) → 21-acetoxy-pregna-4,9(11),16-triene-3,20-dinone (23460-76-6)

Guidance literature:

anecortave; With N-chloro-succinimide; In N,N-dimethyl-formamide; at -15 ℃; for 1.5h; Inert atmosphere;

With sulfur dioxide; In N,N-dimethyl-formamide; at -10 ℃; for 0.5h; Inert atmosphere;

Reference yield: 78.0%

C21H25ClO2 + acetic anhydride (108-24-7) → 21-Acetoxypregna-4,9(11),16-trien-3,20-dion (23460-76-6)

Guidance literature:

With potassium acetate; In N,N-dimethyl-formamide; at 110 ℃; for 3h; Inert atmosphere;

Reference yield: 70.0%

9α-chloro-21-acetoxy-17α-(3-iodobenzoyloxy)-4-pregnene-3,20-dione (74176-89-9) → 21-acetoxy-pregna-4,9(11),16-triene-3,20-dinone (23460-76-6)

Guidance literature:

upstream raw materials:

acetic anhydride

Androstadien-(4,9,⁽¹¹⁾)-dion-3,17

21-acetoxy-11α-(toluene-4-sulfonyloxy)-pregna-4,16-diene-3,20-dione

21-Hydroxypregna-4,9⁽¹¹⁾,16-triene-3,20-dione

Downstream raw materials:

21-Acetoxy-1,4,9⁽¹¹⁾,16-pregnatetraen-3,20-dion

(8S,9R,10S,11S,13S,14S)-9-Fluoro-11-hydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15-dodecahydro-cyclopenta[a]phenanthren-3-one

halcinonide

16α-17-[(1-methylethylidene)bis(oxy)]-11β,21-dihydroxy-9-fluoro-4-ene-pregna-3,20-dione

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、 -. "Preparation method of halcinonide and derivative thereof". Paragraph 0110-0112; 0120; 0123. . Retrieved 2018/03/26.