9-Fluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate

Base Information

• Chemical Name: 9-Fluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate
• CAS No.: 1250-85-7
• Molecular Formula: C23H27 F O5
• Molecular Weight: 402.463
• European Community (EC) Number: 215-006-0
• DSSTox Substance ID: DTXSID90154546
• Nikkaji Number: J217.080I
• Wikidata: Q83021802
• Mol file: 1250-85-7.mol

Synonyms:1250-85-7;EINECS 215-006-0;9-Fluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate;[2-[(8S,9R,10S,11S,13S,14S)-9-fluoro-11-hydroxy-10,13-dimethyl-3-oxo-7,8,11,12,14,15-hexahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;C23H27FO5;21-Acetoxy-9alpha-fluoro-11beta-hydroxypregna-1,4,16-triene-3,20-dione;Pregna-1,4,16-triene-3,20-dione, 21-(acetyloxy)-9-fluoro-11-hydroxy-, (11beta)-;SCHEMBL6323667;DTXSID90154546;C23-H27-F-O5;AKOS030254767;21-acetoxy-9alpha-fluoro-11beta-hydroxy-pregna-1,4,16-triene-3,20-dione;21-Acetyloxy-9-fluoro-11beta-hydroxypregna-1,4,16-triene-3,20-dione

Chemical Property of 9-Fluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate

Chemical Property:

• Melting Point: 215-220 °C
• Boiling Point: 550.1°Cat760mmHg
• PKA: 13.13±0.70(Predicted)
• Flash Point: 286.5°C
• PSA: 80.67000
• Density: 1.28g/cm³
• LogP: 3.02570
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 402.18425212
• Heavy Atom Count: 29
• Complexity: 886

Purity/Quality:

98%Min ^*data from raw suppliers

21-Acetoxy-9α-fluoro-11β-hydroxypregna-1,4,16-triene-3,20-dione ^*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(C3(C2CCC4=CC(=O)C=CC43C)F)O)C
• Isomeric SMILES: CC(=O)OCC(=O)C1=CC[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)O)C
• Uses: 21-Acyloxycorticosteroid derivative. Antiinflammatory.

Technology Process of 9-Fluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate

There total 7 articles about 9-Fluoro-11beta,21-dihydroxypregna-1,4,16-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: 84.5%

1,4-pregnane-9α-fluoro-11β,17α,21-triol-3,20-dione 17,21-diacetate (39987-51-4) → 9α-Fluoro-11β,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate (1250-85-7)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 100 ℃; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

Reference yield:

isoflupredone (338-95-4) → 9α-Fluoro-11β,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate (1250-85-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 7.2 g / PPTS / dimethylformamide; benzene / Heating

2: 4.7 g / 2percent AcOH / dimethylformamide; methanol / Ambient temperature

3: 3.4 g / pyridine / Ambient temperature

4: 1.48 g / AcOK / dimethylformamide / Heating

With pyridine; potassium acetate; pyridinium p-toluenesulfonate; acetic acid; In methanol; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0039-128X(97)00020-2

Reference yield:

Acetic acid (8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11-hydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester (3793-90-6) → 9α-Fluoro-11β,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate (1250-85-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.4 g / pyridine / Ambient temperature

2: 1.48 g / AcOK / dimethylformamide / Heating

With pyridine; potassium acetate; In N,N-dimethyl-formamide;

DOI:10.1016/S0039-128X(97)00020-2

upstream raw materials:

1,4-pregnane-9α-fluoro-11β,17α,21-triol-3,20-dione 17,21-diacetate

isoflupredone

isoflupredone acetate

Acetic acid (8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11-hydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester

Downstream raw materials:

triamcinolone acetonide

(11β,16α)-21-acetyloxy-9-fluoro-11,16,17-trihydroxypegna-1,4-diene-3,20-dione

Acetic acid 2-((1S,3R,4aS,4bS,10aS,10bR,11S,12aS)-10b-fluoro-11-hydroxy-1,3-dimethoxy-10a,12a-dimethyl-8-oxo-3,4,4a,4b,5,6,8,10a,10b,11,12,12a-dodecahydro-1H-2-oxa-chrysen-1-yl)-2-oxo-ethyl ester

methyl 9α-fluoro-11β,21-dihydroxy-3,20-dioxo-pregna-1,4-diene-16α-carboxylate