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CAS No. : | 805245-41-4 | MDL No. : | MFCD25977137 |
Formula : | C44H45FO4Si | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FGVFROJJJDOTDT-RJBDQUNGSA-N |
M.W : | 684.91 | Pubchem ID : | 86268842 |
Synonyms : |
|
Num. heavy atoms : | 50 |
Num. arom. heavy atoms : | 30 |
Fraction Csp3 : | 0.27 |
Num. rotatable bonds : | 11 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 200.39 |
TPSA : | 36.92 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -3.59 cm/s |
Log Po/w (iLOGP) : | 6.04 |
Log Po/w (XLOGP3) : | 9.7 |
Log Po/w (WLOGP) : | 9.01 |
Log Po/w (MLOGP) : | 6.04 |
Log Po/w (SILICOS-IT) : | 8.18 |
Consensus Log Po/w : | 7.79 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | -9.92 |
Solubility : | 0.0000000832 mg/ml ; 0.0000000001 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -10.39 |
Solubility : | 0.0000000278 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
Log S (SILICOS-IT) : | -14.75 |
Solubility : | 0.0 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 7.63 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With n-butyllithium; N-fluorobis(benzenesulfon)imide In tetrahydrofuran; hexane at -78℃; for 1 h; | (3R,4R,6aR)-tert-Butyl-(5-fluoro-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yloxy)-diphenyl-silane (11) To a stirred solution of 10 (11.66 g, 14.71 mmol) and N-fluorobenzenesulfonimide (5.566 g, 17.65 mmol) in dry tetrahydrofuran (100 ml) was slowly added n-butyllithum (27.6 ml, 44.13 mmol, 1.6 M solution in hexanes) at -78° C. under nitrogen atmosphere and the reaction mixture was stirred at the same temperature for 1 hour. The mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by flash silica gel column chromatography (hexane:ethyl acetate=6:1) to afford 11 (7.35 g, 73percent) as a white solid; 1H NMR (400 MHz, CDCl3) δ 7.81-7.17 (m, 25H), 4.94 (t, J=7.2 Hz, 1H), 4.35 (m, 1H), 4.25 (m, 1H), 3.89 (t, J=12.0 Hz, 1H), 3.77 (t, J=12.0 Hz, 1H), 1.42 (s, 3H), 1.38 (s, 3H), 1.08 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With n-butyllithium; N-fluorobis(benzenesulfon)imide In tetrahydrofuran; hexane; n-heptane; tert-butyl methyl ether at -78℃; for 1.5 h; Inert atmosphere | n-Butyllithium (11 mL, 17.6 mmol, 1.6M solution in hexanes)was added dropwise to a cooled (78 °C) solution of 7 [9] (5.58 g,7.04 mmol) and N-fluorobenzenesulfonimide (3.33 g, 10.56 mmol)in anhydrous THF/tert-butyl methyl ether/n-heptane (3:1:1.5,90 mL total, 0.08 M) over a period of 1 h under N2. After stirring atthe same temperature for 30 min, the reaction mixture wasquenched with saturated aqueous NH4Cl (100 mL) and was dilutedwith EtOAc (100 mL). Then the layers were separated and theaqueous layer was extracted with EtOAc (2 x 50 mL). The combinedorganic layers were washed successively with H2O and brine, driedover anhydrous MgSO4, filtered, and evaporated. Finally, the residuewas purified by medium pressure liquid chromatography(silica gel, hexanes/EtOAc = 25/1) to give vinyl fluoride 8a (2.17 g,45percent), 8b (1.03 g, 22percent) and 8c (0.84 g, 18percent).8a: [α]D25-8.42 (c 0.19, MeOH); 1H NMR (400 MHz, CDCl3)δ 7.80 (d, J 6.6 Hz, 2 H), 7.72 (d, J 6.6 Hz, 2 H), 7.35-7.44 (m,13 H), 7.16-7.27 (m, 8 H), 4.93 (t, J = 6.6 Hz, 1 H), 4.34 (s, 1 H),3.22-3.25 (m, 1 H), 3.89 (d, J = 11.8 Hz, 1 H), 3.77 (d, J = 12.3 Hz,1 H), 1.44 (s, 3 H), 1.38 (s, 3 H), 1.07 (s, 9 H); 13C NMR (100 MHz,CDCl3) δ 157.3 (d, J = 288.0 Hz), 143.8, 136.0 (d, J = 23.1 Hz), 133.5 (d,J = 21.2 Hz), 129.7 (d, J = 4.9 Hz), 127.7, 127.5 (d, J = 9.2 Hz), 127.0,115.6 (d, J = 4.2 Hz), 111.8, 87.0, 78.6 (d, J = 8.8 Hz), 75.3 (d,J = 7.2 Hz), 71.0 (d, J = 18.9 Hz), 56.3, 29.5 (d, J = 29.8), 27.9, 27.2,26.7, 19.4; 19F NMR (376 MHz, CDCl3) δ -128.2; MS (ESI+) found707.2968 [calcd for C44H45FNaO4Si (M + Na)+ 707.2969]. |