Cas no 910-99-6 (Pregna-1,4,9(11)-triene-3,20-dione,21-(acetyloxy)-17-hydroxy-16-methyl-, (16b)-)

Pregna-1,4,9(11)-triene-3,20-dione,21-(acetyloxy)-17-hydroxy-16-methyl-, (16b)- structure
910-99-6 structure
Product Name:Pregna-1,4,9(11)-triene-3,20-dione,21-(acetyloxy)-17-hydroxy-16-methyl-, (16b)-
CAS No:910-99-6
MF:C24H30O5
MW:398.492007732391
CID:808470
Update Time:2023-11-06

Pregna-1,4,9(11)-triene-3,20-dione,21-(acetyloxy)-17-hydroxy-16-methyl-, (16b)- Chemical and Physical Properties

Names and Identifiers

    • Pregna-1,4,9(11)-triene-3,20-dione,21-(acetyloxy)-17-hydroxy-16-methyl-, (16b)-
    • 17,21-dihydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione 21-acetate
    • 17-Hydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione 21-acetate
    • (16β)-21-(Acetyloxy)-17-hydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione (ACI)
    • Pregna-1,4,9(11)-triene-3,20-dione, 17,21-dihydroxy-16β-methyl-, 21-acetate (6CI, 7CI, 8CI)
    • Inchi： 1S/C24H30O5/c1-14-11-20-18-6-5-16-12-17(26)7-9-22(16,3)19(18)8-10-23(20,4)24(14,28)21(27)13-29-15(2)25/h7-9,12,14,18,20,28H,5-6,10-11,13H2,1-4H3/t14-,18+,20-,22-,23-,24-/m0/s1
    • InChI Key： AAPZMQVULRVUEU-NZDAKWCRSA-N
    • SMILES： C[C@@]12[C@@](O)(C(=O)COC(=O)C)[C@@H](C)C[C@H]1[C@@H]1CCC3=CC(C=C[C@]3(C)C1=CC2)=O

Computed Properties

  • Exact Mass: 398.209324
  • Monoisotopic Mass: 398.209324
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 29
  • Rotatable Bond Count: 4
  • Complexity: 880
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 6
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 80.7

Experimental Properties

  • Density: 1.22
  • Boiling Point: 560°C at 760 mmHg
  • Flash Point: 189.6°C
  • Refractive Index: 1.58

Pregna-1,4,9(11)-triene-3,20-dione,21-(acetyloxy)-17-hydroxy-16-methyl-, (16b)- Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: (SP-4-2)-Chlorotris(triphenylphosphine)rhodium
Reference
Convenient access to 16-methylene and 16β-methyl corticosteroids by a novel transformation of geminal bis(phenylsulfinyl) intermediates
Boivin, Jean; Chauvet, Christine; Zard, Samir Z., Tetrahedron Letters, 1992, 33(34), 4913-16

Production Method 2

Reaction Conditions
1.1 Reagents: Sodium acetate Solvents: Dimethylformamide ;  1 h, rt; rt → 35 °C; 1 h, 35 °C; 35 °C → 62 °C; 2 h, 58 - 62 °C; 62 °C → rt
Reference
Method for preparation of Betamethasone and its derivative
, China, , ,

Production Method 3

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Acetic acid ,  Dimethylformamide ;  rt → 90 °C; 0.5 h, 85 - 90 °C; 90 °C → 60 °C; 1 h, 50 - 60 °C; 60 °C → 20 °C
1.2 Solvents: Acetone ,  Dimethylformamide ;  1 h, rt; 2 h, reflux
1.3 Reagents: Water ;  1 h, cooled
Reference
Synthesis improvement in betamethasone
Huang, Yun; Wan, Neng; Ding, Ying; Xiao, Fang-qing, Zhongnan Yaoxue, 2014, 12(9), 880-881

Pregna-1,4,9(11)-triene-3,20-dione,21-(acetyloxy)-17-hydroxy-16-methyl-, (16b)- Raw materials

Pregna-1,4,9(11)-triene-3,20-dione,21-(acetyloxy)-17-hydroxy-16-methyl-, (16b)- Preparation Products

Pregna-1,4,9(11)-triene-3,20-dione,21-(acetyloxy)-17-hydroxy-16-methyl-, (16b)- Related Literature

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