(6Alpha,11beta)-6,9-Difluoro-11,17,21-trihydroxypregna-1,4-diene-3,20-dione

C₂₁H₂₆F₂O₅CAS 806-29-1396.43 g/mol

Properties

Molecular formula: C₂₁H₂₆F₂O₅
Molar mass: 396.43 g/mol
Exact mass: 396.1748 Da
Melting point: 250–257 °C (decomposes)
logP: 1.60Crippen estimate
Polar surface area: 94.8 Å²
H-bond donors / acceptors: 3 / 5
Rotatable bonds: 2
Stereocentres: S, S, S, S, R, S, S, Rin SMILES atom order

Hazards

Not classified as hazardous under GHS. Aggregated from the ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Identifiers

CAS number

806-29-1

SMILES

C[C@]12C=CC(=O)C=C1[C@@H](F)C[C@H]1[C@@H]3CC[C@](O)(C(=O)CO)[C@@]3(C)C[C@H](O)[C@@]12F

InChIKey

ABUISBDTYAZRHY-RBKZJGKHSA-N

InChI

InChI=1S/C21H26F2O5/c1-18-5-3-11(25)7-14(18)15(22)8-13-12-4-6-20(28,17(27)10-24)19(12,2)9-16(26)21(13,18)23/h3,5,7,12-13,15-16,24,26,28H,4,6,8-10H2,1-2H3/t12-,13-,15-,16-,18-,19-,20-,21-/m0/s1

Characterization data

Calculated from the structure, in the form journals print them.

¹H NMR

Predicted ¹H NMR (400 MHz, CDCl₃) δ 6.68 (d, J = 10.0 Hz, 1H), 6.14 (s, 1H), 6.03 (d, J = 10.0 Hz, 1H), 5.24 (dt, J = 7.0 Hz, J(H,F) = 47.0 Hz, 1H), 4.56 (s, 2H), 4.34 (dt, J = 7.0 Hz, J(H,F) = 21.0 Hz, 1H), 2.07 (t, J = 7.0 Hz, 2H), 2.05 (m, J = 7.0 Hz, J(H,F) = 21.0 Hz, 2H), 2.00 (br s, 1H), 2.00 (br s, 1H), 2.00 (br s, 1H), 1.97 (m, J = 7.0 Hz, J(H,F) = 21.0 Hz, 1H), 1.79 (d, J = 7.0 Hz, 2H), 1.51 (m, J = 7.0 Hz, 1H), 1.51 (m, J = 7.0 Hz, 2H), 1.06 (s, 3H), 0.86 (s, 3H).

¹³C NMR

Predicted ¹³C NMR (101 MHz, CDCl₃) δ 208.7, 191.7, 156.2 (dd, J(C,F) = 20.0, 5.0 Hz), 150.5 (d, J(C,F) = 5.0 Hz), 126.0 (d, J(C,F) = 168.0 Hz), 118.8, 115.6 (d, J(C,F) = 5.0 Hz), 101.2, 86.1 (d, J(C,F) = 168.0 Hz), 77.4 (d, J(C,F) = 20.0 Hz), 71.4, 60.9 (dd, J(C,F) = 20.0, 5.0 Hz), 60.8, 59.3 (d, J(C,F) = 5.0 Hz), 54.2 (dd, J(C,F) = 20.0, 5.0 Hz), 42.4 (d, J(C,F) = 5.0 Hz), 31.9 (dd, J(C,F) = 20.0, 5.0 Hz), 31.8, 26.3, 16.0 (d, J(C,F) = 5.0 Hz), 13.6.

[M + H]+

[M + H]+ Calcd for C21H27F2O5 397.1821

[M + Na]+

[M + Na]+ Calcd for C21H26F2NaO5 419.1641

[M − H]−

[M − H]− Calcd for C21H25F2O5 395.1676

Elemental analysis

Anal. Calcd for C21H26F2O5: C, 63.63; H, 6.61.