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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
|
Chemical Name : | (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dichromen-7(7aH)-one |
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: |
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* 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 |
---|---|---|
35% | With iodine; sodium acetate; In ethanol; for 12.0h;Reflux; | Example 5 Preparation of 9,10-Dimethoxy-3,3-dimethyl-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7-(13H)-one (12) Sodium acetate (21 mg, 0.25 mmol) and I2 (290 mg, 1.14 mmol) were added to ethyl alcohol (2.0 mL) containing <strong>[522-17-8]deguelin</strong> (50 mg, 0.13 mmol) of Comparative Example 1 dissolved therein at room temperature. The mixture was refluxed for 12 hours, cooled down at room temperature, and extracted with EtOAc. The organic layer of the extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. Then, the obtained residue was crystallized in EtOAc:n-hexane=1:1 solution to give the compound 12 of Example 5 as a light-yellow solid (yield: 35percent, 17 mg). 1H-NMR (CDCl3, 500 MHz) delta 8.42 (s, 1H), 8.01 (d, 1H, J = 8.7 Hz), 6.84 (d, 1H, J = 8.7 Hz), 6.73 (d, 1H, J = 10.0 Hz), 6.52 (s, 1H), 5.70 (d, 1H, J = 8.7 Hz), 4.99 (s, 2H), 3.93 (s, 3H), 3.84 (s, 3H), 1.47 (s, 6H).; 13C-NMR (CDCl3, 125 MHz) delta 174.2, 157.1, 156.1, 151.0, 148.9, 146.2, 144.0, 130.5, 126.4, 118.4, 115.3, 114.6, 111.7, 110.5, 109.9, 109.0, 100.3, 77.7, 64.8, 56.2, 55.8, 28.1, 28.1; HRMS (FAB) Calcd for C23H20O6 (M+) : 392.1260, Found: 392.1263. |
35% | With iodine; sodium acetate; In ethanol; at 20℃; for 12.0h; | Sodium acetate (21 mg, 0.25 mmol) and I2 (290 mg, 1.14 mmol) were added to ethyl alcohol (2.0 mL) containing <strong>[522-17-8]deguelin</strong> (50 mg, 0.13 mmol) of Comparative Example 1 dissolved therein at room temperature. The mixture was refluxed for 12 hours, cooled down at room temperature, and extracted with EtOAc. The organic layer of the extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. Then, the obtained residue was crystallized in EtOAc: n-hexane=1:1 solution to give the compound 12 of Example 5 as a light-yellow solid (yield: 35percent, 17 mg). [0344] 1H-NMR (CDCl3, 500 MHz) delta 8.42 (s, 1H), 8.01 (d, 1H, J=8.7 Hz), 6.84 (d, 1H, J=8.7 Hz), 6.73 (d, 1H, J=10.0 Hz), 6.52 (s, 1H), 5.70 (d, 1H, J=8.7 Hz), 4.99 (s, 2H), 3.93 (s, 3H), 3.84 (s, 3H), 1.47 (s, 6H). [0345] 13C-NMR (CDCl3, 125 MHz) delta 174.2, 157.1, 156.1, 151.0, 148.9, 146.2, 144.0, 130.5, 126.4, 118.4, 115.3, 114.6, 111.7, 110.5, 109.9, 109.0, 100.3, 77.7, 64.8, 56.2, 55.8, 28.1, 28.1; [0346] HRMS (FAB) Calcd for C23H20O6 (M+): 392.1260. Found: 392.1263. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | 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) delta 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) delta 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% | 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) delta 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) delta 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. | |
Solid PhSe-Cl (185 mg, 0.972 mmol) is added to a cooled (-30° C.) solution of (-)-rot-2'enonic acid (350 mg, 0.884 mmol) in dichloromethane (10.5 mL). After completion of addition the reaction mixture is allowed to warm to room temperature over 2 h and continues to stir at room temperature for an additional hour. After three hours of total reaction time the reaction mixture is concentrated to yield a yellow oil. The crude material is dissolved in THF (10.5 mL) and cooled to 0° C. Hydrogen peroxide (30percent in water, 0.177 mL) is added. After completion of addition the reaction mixture continues to stir at 0° C. for one hour and then stirs at room temperature overnight. The next day the reaction mixture is diluted with diethyl ether. The organic layer is separated and washed with 5percent NaHCO3 (2.x.), dried over Na2SO4 and concentrated to yield (6aS, 12aS)-deguelin as a yellow amorphous solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid; trimethyl orthoformate; In methanol; at 20℃;Heating / reflux; | Synthesis of (6aS)-<strong>[522-17-8]deguelin</strong> enol ether To a solution of <strong>[522-17-8]deguelin</strong> (245 mg, 0.622 mmol) in methanol (20 ml) is added p-TsOH monohydrate (118.3 mg, 0.622 mmol) and trimethyl orthoformate (68.14 muL, 0.622 mmol). After completion of addition the reaction mixture is heated to reflux for 8 h and then continues to stir at room temperature overnight. The next day the reaction mixture is diluted with water. The aqueous layer is extracted with ethyl acetate. Combined organic layers are washed with sat. NaHCO3, dried over Na2SO4 and concentrated to yield (6aS)-<strong>[522-17-8]deguelin</strong> enol ether as a yellow amorphous solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium thiomethoxide; In N,N-dimethyl acetamide; at 80℃; for 26.0h; | Synthesis of (6aS,12aS)-2-0-desmethyl<strong>[522-17-8]deguelin</strong> (6aS, 12aS)-Deguelin (251 mg, 0.638 mmol) and sodium methanethiolate (125 mg, 1.78 mmol) are dissolved in 4 ml of N,N-dimethylacetamide and heated at 80° C. for 26 h. The reaction mixture is diluted to 50 ml with water and extracted with dichloromethane. The aqueous layer is then acidified with 5percent HCl and extracted again with dichloromethane. All of the organic layers are dried over Na2SO4, concentrated, and purified using silica gel chromatography (100percent dichloromethane to 30percent acetone in dichloromethane) to yield (6aS,12aS)-2-0-desmethyl<strong>[522-17-8]deguelin</strong>. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium tetrahydroborate; In methanol; at 0℃; for 0.5h; | Manufacturing Example 43: Preparation of (7S,7aR,13aS)-9,10-Dimethoxy-3,3-dimethyl-7,7a,13,13a-tetrahydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7-ol (14) NaBH4 (43 mg, 1.13 mmol) was added to methanol (10.0 mL) containing <strong>[522-17-8]deguelin</strong> (300 mg, 0.76 mmol) dissolved therein at 0°C, followed by stirring for 30 minutes. The mixture was cooled down with water. The mixture was extracted with diethyl ether. The organic layer was washed with brine, dried over MgSO4, and concentrated. Then, the obtained residue was purified by flash column chromatography (EtOAc:n-hexane=1:1) to give the compound 14 of Manufacturing Example 43 as a white solid (yield: 100percent, 300 mg). 1H-NMR (CDCl3, 400 MHz) delta 6.99 (d, 1H, J = 8.2 Hz), 6.68 (s, 1H), 6.64 (d, 1H, J = 10.0 Hz), 6.47 (s, 1H), 6.41 (d, 1H, J = 8.2 Hz), 5.56 (d, 1H, J = 10.0 Hz), 4.80 (m, 2H), 4.57 (d, 1H, J = 10.0 Hz), 4.21 (m, 1H), 3.84 (s, 3H), 3.82 (s, 3H), 3.36 (t, 1H, J = 4.9 Hz), 1.41 (s, 3H), 1.39 (s, 3H); 13C-NMR (CDCl3, 100 MHz) delta 154.3, 149.6, 149.4, 147.9, 143.8, 130.0, 129.1, 116.4, 113.6, 111.3, 109.8, 109.5, 108.7, 100.7, 76.0, 69.1, 66.3, 65.0, 56.5, 55.8, 37.9, 27.8, 27.7; HRMS (FAB) Calcd for C23H24O6 (M+H+) : 396.1560, Found: 396.1562. |
100% | With sodium tetrahydroborate; In methanol; at 0℃; for 0.5h; | NaBH4 (43 mg, 1.13 mmol) was added to methanol (10.0 mL) containing <strong>[522-17-8]deguelin</strong> (300 mg, 0.76 mmol) dissolved therein at 0° C., followed by stirring for 30 minutes. The mixture was cooled down with water. The mixture was extracted with diethyl ether. The organic layer was washed with brine, dried over MgSO4, and concentrated. Then, the obtained residue was purified by flash column chromatography (EtOAc:n-hexane=1:1) to give the compound 14 of Manufacturing Example 43 as a white solid (yield: 100percent, 300 mg). [0319] 1H-NMR (CDCl3, 400 MHz) delta 6.99 (d, 1H, J=8.2 Hz), 6.68 (s, 1H), 6.64 (d, 1H, J=10.0 Hz), 6.47 (s, 1H), 6.41 (d, 1H, J=8.2 Hz), 5.56 (d, 1H, J=10.0 Hz), 4.80 (m, 2H), 4.57 (d, 1H, J=10.0 Hz), 4.21 (m, 1H), 3.84 (s, 3H), 3.82 (s, 3H), 3.36 (t, 1H, J=4.9 Hz), 1.41 (s, 3H), 1.39 (s, 3H); [0320] 13C-NMR (CDCl3, 100 MHz) delta 154.3, 149.6, 149.4, 147.9, 143.8, 130.0, 129.1, 116.4, 113.6, 111.3, 109.8, 109.5, 108.7, 100.7, 76.0, 69.1, 66.3, 65.0, 56.5, 55.8, 37.9, 27.8, 27.7; [0321] HRMS (FAB) Calcd for C23H24O6 (M+H+): 396.1560. Found: 396.1562. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With hydroxylamine hydrochloride; sodium hydroxide; In ethanol; at 60℃; for 2.0h;Inert atmosphere; | A solution containing <strong>[522-17-8]deguelin</strong> (1.0 equiv, 15 mg, 38 mumol), hydroxylamine hydrochloride (10 equiv, 26 mg, 0.4 mmol), sodium hydroxide (10 equiv, 15 mg, 0.4 mmol) and H2O (15 muL) in EtOH (1 mL) was heated at 60 °C for 2 h. The reaction was then neutralized by adding 10percent aqueous HCl solution (1.0 mL) and water (1.0 mL). The aqueous layer was extracted with EtOAc (3 .x. 2.0 mL) and the combined organic layers were dried over Na2SO4 and filtered. The solvent was concentrated under reduced pressure and the residue was purified by column chromatography (SiO2, from 70/30 petroleum ether/EtOAc to 100percent EtOAc) to afford oxime 6 (10 mg, 67percent) as a foam. 1H NMR (400 MHz, CDCl3, 23 °C): delta 9.82 (s, OH), 7.52 (d, J = 8.6 Hz, 1H), 6.70 (s, 1H), 6.70 (d, J = 10.0 Hz, 1H), 6.47 (d, J = 8.6 Hz, 1H), 6.44 (s, 1H) 5.58 (d, J = 10.0 Hz, 1H), 4.98 (d, J = 9.0 Hz, 1H), 4.78 (d, J = 9.0, 1H), 4.59 (d, J = 12.0 Hz, 1H), 4.07 (d, J = 12.0 Hz, 1H), 3.77 (s, 3H), 3.60 (s, 3H), 1.43 (s, 3H), 1.41 (s, 3H) ppm; 13C NMR (100 MHz, acetone-d6, 23 °C): delta 163.7, 157.5, 155.6, 151.7, 151.5, 146.0, 132.0, 131.0, 117.9, 114.8, 111.5, 111.4, 109.8, 108.8, 103.9, 81.5, 78.4, 65.9, 57.5, 57.0, 46.7, 29.2, 29.0 ppm. |
26 mg | With pyridine; hydroxylamine hydrochloride; at 70℃; | Example 16 Preparation of (7aR,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one oxime (23) Hydroxylamine hydrochloride (14 mg, 0.19 mmol) was added to anhydrous pyridine (1.0 mL) containing <strong>[522-17-8]deguelin</strong> (25 mg, 0.063 mmol) prepared in Comparative Example 1. The reaction temperature was increased to 70°C. While monitoring with TLC, the reaction mixture was stirred until the reaction was completed. The mixture was cooled down with water (0.5 mL), followed by extraction with CH2Cl2. The organic layer of the extract was washed with 2 N-HCl aqueous solution, water, and brine stepwise. The solvent was eliminated under reduced pressure and the residue was dried over MgSO4, filtered, and concentrated. Then, the obtained residue was purified by flash column chromatography (EtOAc:n-hexane=1:2) to give the compound 23 of Example 16 as a white solid (26 mg). 1H-NMR (CDCl3, 500 MHz) delta 8.26 (br, 1H), 7.59 (d, 1H, J = 8.7 Hz), 6.62 (m, 2H), 6.41 (s, 1H), 6.37 (d, 1H, J = 8.7 Hz), 5.49 (d, 1H, J = 10.0 Hz), 4.84 (d, 1H, J = 3.2 Hz), 4.61 (dd, 1H, J = 12.0, 2.4 Hz), 4.48 (m, 1H), 4.24 (d, 1H, J = 12.0 Hz), 3.79 (s, 3H), 3.72 (s, 3H), 1.39 (s, 3H), 1.34 (s, 3H); 13C-NMR (CDCl3, 125 MHz) delta155.7, 151.6, 151.3, 149.3, 147.7, 143.6, 128.6, 124.5, 116.2, 112.2, 110.7, 109.8, 108.2, 106.2, 100.6, 76.5, 69.6, 66.8, 56.4, 55.8, 31.6, 28.1, 27.8; HRMS (FAB) Calcd for C23H23NO6 (M+): 409.1525, Found: 409.1513. |
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