6-alpha-Fluoro-isoflupredone

Base Information

• Chemical Name: 6-alpha-Fluoro-isoflupredone
• CAS No.: 806-29-1
• Molecular Formula: C21H26F2O5
• Molecular Weight: 396.431
• Hs Code.: 2937210000
• European Community (EC) Number: 212-360-8
• NSC Number: 77021
• UNII: MR5YQC763Y
• DSSTox Substance ID: DTXSID501160438
• Nikkaji Number: J193.187C
• ChEMBL ID: CHEMBL1967506
• Mol file: 806-29-1.mol

Synonyms:806-29-1;6-alpha-Fluoro-isoflupredone;NSC77021;(6S,8S,9R,10S,11S,13S,14S,17R)-6,9-Difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one;6alpha,9alpha-difluoroprednisolone;(6S,8S,9R,10S,11S,13S,14S,17R)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one;EINECS 212-360-8;NSC 77021;NSC-77021;6alpha,9-Difluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione;C21H26F2O5;(6alpha,11beta)-6,9-difluoro-11,17,21-trihydroxypregna-1,4-diene-3,20-dione;6-alpha-Fluoroisoflupredone;MLS002701913;C21-H26-F2-O5;6a-Fluoro-isoflupredone;6--Fluoro-isoflupredone;MR5YQC763Y;6alpha,9-Difluoroprednisolone;SCHEMBL3765700;CHEMBL1967506;6.alpha.,9-Difluoroprednisolone;DTXSID501160438;AKOS025402049;AC-3529;6.alpha.,9.alpha.-Difluoroprednisolone;AS-59362;NCI60_041694;CS-0199244;A854253;Q-101390;Pregna-1,20-dione, 6.alpha.,9-difluoro-11.beta.,17,21-trihydroxy-;Pregna-1,4-diene-3,20-dione, 6alpha,9-difluoro-11beta,17,21-trihydroxy-;Pregna-1,20-dione, 6,9-difluoro-11,17,21-trihydroxy-, (6.alpha.,11.beta.)-;Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,17,21-trihydroxy-, (6alpha,11beta)-

Chemical Property of 6-alpha-Fluoro-isoflupredone

Chemical Property:

• Vapor Pressure: 2.79E-15mmHg at 25°C
• Melting Point: 250-257 °C (decomp)
• Refractive Index: 1.586
• Boiling Point: 568.3 °C at 760 mmHg
• PKA: 11.96±0.70(Predicted)
• Flash Point: 297.5 °C
• PSA: 94.83000
• Density: 1.39 g/cm³
• LogP: 1.59770
• Storage Temp.: 2-8°C
• Solubility.: Dioxane (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 396.17483025
• Heavy Atom Count: 28
• Complexity: 809

Purity/Quality:

98%,99%, ^*data from raw suppliers

6α,?9α-?Difluoroprednisolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC(C3(C(C1CCC2(C(=O)CO)O)CC(C4=CC(=O)C=CC43C)F)F)O
• Isomeric SMILES: C[C@]12C[C@@H]([C@]3([C@H]([C@@H]1CC[C@@]2(C(=O)CO)O)C[C@@H](C4=CC(=O)C=C[C@@]43C)F)F)O
• Uses: 6α,9α-Difluoroprednisolone has shown to increase metastases and increase glucocorticoid activity in C57/BL6 mice.

Technology Process of 6-alpha-Fluoro-isoflupredone

There total 4 articles about 6-alpha-Fluoro-isoflupredone 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:

21-acetoxy-6α,9-difluoro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione (52-70-0) → 6α,9-difluoro-11β,17,21-trihydroxy-pregna-1,4-diene-3,20-dione (806-29-1)

Guidance literature:

With potassium hydrogencarbonate;

Reference yield:

21-acetoxy-9,11β-epoxy-6α-fluoro-17-hydroxy-9β-pregna-1,4-diene-3,20-dione (3802-45-7) → 6α,9-difluoro-11β,17,21-trihydroxy-pregna-1,4-diene-3,20-dione (806-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1: HF

2: aqueous methanol.KHCO₃

With hydrogen fluoride; potassium hydrogencarbonate;

Reference yield:

→ 6α,9α-Difluor-16α-methyl-1,4-pregnadien-11β,17α,21-triol-3,20-dion (806-29-1,60864-55-3)

Guidance literature:

9,11-Epoxid-21-trimethylacetat, 1) HF, 2) NH3;

upstream raw materials:

21-acetoxy-6α,9-difluoro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione

21-acetoxy-9,11β-epoxy-6α-fluoro-17-hydroxy-9β-pregna-1,4-diene-3,20-dione

Downstream raw materials:

(6α,11β)-6,9-difluoro-11,21-dihydroxy-3,20-dioxopregna-1,4-dien-17-yl 4-(benzyloxy)benzoate