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CAS No. : | 522-17-8 | MDL No. : | MFCD01740600 |
Formula : | C23H22O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ORDAZKGHSNRHTD-UXHICEINSA-N |
M.W : | 394.42 | Pubchem ID : | 107935 |
Synonyms : |
(-)-Deguelin;(-)-cis-Deguelin;(−)-cis-Deguelin
|
Num. heavy atoms : | 29 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.35 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 106.98 |
TPSA : | 63.22 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.06 cm/s |
Log Po/w (iLOGP) : | 3.86 |
Log Po/w (XLOGP3) : | 3.72 |
Log Po/w (WLOGP) : | 3.9 |
Log Po/w (MLOGP) : | 1.93 |
Log Po/w (SILICOS-IT) : | 4.11 |
Consensus Log Po/w : | 3.5 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.8 |
Solubility : | 0.00621 mg/ml ; 0.0000157 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.74 |
Solubility : | 0.00719 mg/ml ; 0.0000182 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.97 |
Solubility : | 0.00042 mg/ml ; 0.00000106 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.67 |
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 |
---|---|---|
61% | Stage #1: With Phenylselenyl chloride In dichloromethane at -30 - 20℃; for 3.16667 h; Inert atmosphere Stage #2: With dihydrogen peroxide In tetrahydrofuran; water at 0℃; |
Comparative Example 1: Preparation of (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one (Deguelin) Phenylselenyl chloride (68 mg, 0.35 mmol) was added to anhydrous CH2Cl2 solution (4.0 mL) containing the compound 8 (128 mg, 0.32 mmol) prepared in Example 1 at -30°C under argon atmosphere, followed by stirring for 10 minutes with maintaining the temperature at -30°C. The temperature was raised to room temperature with stirring for 2 hours, and then additional stirring was performed for 1 more hour. The solvent was eliminated from the reaction mixture under reduced pressure and the obtained residue was dissolved in THF (4.0 mL), to which hydrogen peroxide (30percent in water, 0.06 mL) was added 0°C. The reaction mixture was stirred until the temperature of the mixture reached to room temperature, during which the reaction was monitored with TLC. EtOAc (8.0 mL) and water (4.0 mL) were added thereto. The organic layer was separated, washed with 5percent NaHCO3 aqueous solution and brine, dried over MgSO4, filtered, and then concentrated. The obtained non-purified residue was purified by flash column chromatography (EtOAc:n-hexane=1:2) to give deguelin as a light-yellow solid (yield: 61percent, 78 mg). 1H-NMR (CDCl3, 400 MHz) δ 7.72 (d, 1H, J = 8.7 Hz), 6.77 (s, 1H), 6.62 (d, 1H, J = 10.0 Hz), 6.43 (s, 1H), 6.43 (d, 1H, J = 8.7 Hz), 5.53 (d, 1H, J = 10.0 Hz), 4.89 (m, 1H), 4.61 (dd, 1H, J = 12.0, 3.1 Hz), 4.17 (d, 1H, J = 12.0 Hz), 3.82 (d, 1H, J = 4.1 Hz), 3.78 (s, 3H), 3.75 (s, 3H), 1.43 (s, 3H), 1.36 (s, 3 H) ; 13C-NMR (CDCl3, 100 MHz) δ 189.2, 160.0, 156.9, 149.4, 147.4, 143.8, 128.6, 128.5, 115.7, 112.7, 111.4, 110.4, 109.1, 104.7, 100.9, 77.6, 72.4, 66.2, 56.3, 55.8, 44.3, 28.4, 28.1; HRMS (FAB) Calcd for C23H23O6 (M+H+) : 395.1495, Found: 395.1495. |
61% | Stage #1: With Phenylselenyl chloride In dichloromethane at -30 - 20℃; for 3 h; Inert atmosphere Stage #2: With dihydrogen peroxide In tetrahydrofuran at 0 - 20℃; |
Phenylselenyl chloride (68 mg, 0.35 mmol) was added to anhydrous CH2Cl2 solution (4.0 mL) containing the compound 8 (128 mg, 0.32 mmol) prepared in Example 1 at −30° C. under argon atmosphere, followed by stirring for 10 minutes with maintaining the temperature at −30° C. The temperature was raised to room temperature with stirring for 2 hours, and then additional stirring was performed for 1 more hour. The solvent was eliminated from the reaction mixture under reduced pressure and the obtained residue was dissolved in THF (4.0 mL), to which hydrogen peroxide (30percent in water, 0.06 mL) was added 0° C. The reaction mixture was stirred until the temperature of the mixture reached to room temperature, during which the reaction was monitored with TLC. EtOAc (8.0 mL) and water (4.0 mL) were added thereto. The organic layer was separated, washed with 5percent NaHCO3 aqueous solution and brine, dried over MgSO4, filtered, and then concentrated. The obtained non-purified residue was purified by flash column chromatography (EtOAc:n-hexane=1:2) to give deguelin as a light-yellow solid (yield: 61percent, 78 mg). [0584] 1H-NMR (CDCl3, 400 MHz) δ 7.72 (d, 1H, J=8.7 Hz), 6.77 (s, 1H), 6.62 (d, 1H, J=10.0 Hz), 6.43 (s, 1H), 6.43 (d, 1H, J=8.7 Hz), 5.53 (d, 1H, J=10.0 Hz), 4.89 (m, 1H), 4.61 (dd, 1H, J=12.0, 3.1 Hz), 4.17 (d, 1H, J=12.0 Hz), 3.82 (d, 1H, J=4.1 Hz), 3.78 (s, 3H), 3.75 (s, 3H), 1.43 (s, 3H), 1.36 (s, 3H); [0585] 13C-NMR (CDCl3, 100 MHz) δ 189.2, 160.0, 156.9, 149.4, 147.4, 143.8, 128.6, 128.5, 115.7, 112.7, 111.4, 110.4, 109.1, 104.7, 100.9, 77.6, 72.4, 66.2, 56.3, 55.8, 44.3, 28.4, 28.1; [0586] HRMS (FAB) Calcd for C23H23O6 (M+H+): 395.1495. Found: 395.1495. |