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[ CAS No. 38226-86-7 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 38226-86-7
Chemical Structure| 38226-86-7
Structure of 38226-86-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 38226-86-7 ]

CAS No. :38226-86-7 MDL No. :MFCD30573905
Formula : C21H20O6 Boiling Point : -
Linear Structure Formula :- InChI Key :PPCHTBBOSVKORE-UHFFFAOYSA-N
M.W : 368.38 Pubchem ID :14583584
Synonyms :
β-Anhydroicaritin
Chemical Name :3,5-Dihydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-9,10-dihydro-4H,8H-pyrano[2,3-f]chromen-4-one

Calculated chemistry of [ 38226-86-7 ]

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 102.26
TPSA : 89.13 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.52
Log Po/w (XLOGP3) : 4.18
Log Po/w (WLOGP) : 3.98
Log Po/w (MLOGP) : 1.39
Log Po/w (SILICOS-IT) : 4.36
Consensus Log Po/w : 3.49

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.06
Solubility : 0.00318 mg/ml ; 0.00000863 mol/l
Class : Moderately soluble
Log S (Ali) : -5.76
Solubility : 0.000639 mg/ml ; 0.00000174 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.39
Solubility : 0.000151 mg/ml ; 0.00000041 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.74

Safety of [ 38226-86-7 ]

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:

Application In Synthesis of [ 38226-86-7 ]

* 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.

  • Downstream synthetic route of [ 38226-86-7 ]

[ 38226-86-7 ] Synthesis Path-Downstream   1~59

  • 3
  • [ 38226-86-7 ]
  • [ 74-88-4 ]
  • [ 55395-02-3 ]
  • 4
  • C39H50O20 [ No CAS ]
  • [ 38226-86-7 ]
  • 9
  • 3-O-L-rhamnose-7-O-β-glucose-8-prenyl-4'-methoxychrysin [ No CAS ]
  • [ 38226-86-7 ]
  • 10
  • [ 38226-86-7 ]
  • [ 1186604-08-9 ]
  • 11
  • [ 38226-86-7 ]
  • [ 1186604-09-0 ]
  • 12
  • [ 38226-86-7 ]
  • [ 124-63-0 ]
  • [ 1186604-07-8 ]
  • 13
  • [ 38226-86-7 ]
  • cycloicaritin-3-O-glucuronide [ No CAS ]
  • 14
  • [ 349-88-2 ]
  • [ 38226-86-7 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4,8,9,10-tetrahydropyrano[2,3-f]chromen-3-yl 4-fluorobenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.8% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 15
  • [ 2905-21-7 ]
  • [ 38226-86-7 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-9,10-dihydro-4H,8H-pyrano[2,3-f]chromen-3-yl 2-fluorobenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80.5% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 16
  • [ 777-44-6 ]
  • [ 38226-86-7 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4,8,9,10-tetrahydropyrano[2,3-f]chromen-3-yl 3-(trifluoromethyl)benzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.4% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 17
  • [ 2991-42-6 ]
  • [ 38226-86-7 ]
  • C28H23F3O8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.4% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 18
  • [ 38226-86-7 ]
  • [ 98-58-8 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4,8,9,10-tetrahydropyrano[2,3-f]chromen-3-yl 4-bromobenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.4% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 19
  • [ 38226-86-7 ]
  • [ 98-59-9 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4,8,9,10-tetrahydropyrano[2,3-f]chromen-3-yl 4-methylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.6% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 20
  • [ 15084-51-2 ]
  • [ 38226-86-7 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-9,10-dihydro-4H,8H-pyrano[2,3-f]chromen-3-yl 4-(tert-butyl)benzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.9% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 21
  • [ 38226-86-7 ]
  • [ 98-68-0 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4,8,9,10-tetrahydropyrano[2,3-f]chromen-3-yl 4-methoxybenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82.8% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 22
  • [ 23095-31-0 ]
  • [ 38226-86-7 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4,8,9,10-tetrahydropyrano[2,3-f]chromen-3-yl 3,4-dimethoxybenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.4% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 23
  • [ 63624-28-2 ]
  • [ 38226-86-7 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4,8,9,10-tetrahydropyrano[2,3-f]chromen-3-yl 2,4-dimethoxybenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.6% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 24
  • [ 16629-19-9 ]
  • [ 38226-86-7 ]
  • C25H22O8S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.1% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.2-(11-Chlorobenzofuro[3,2-b]quinolin-7-yloxy)-N,N-dimethy-lethanamine (2): Yellow solid; yield 0.2 g, 77.1 %; m. p. 218-219 C; 1 H NMR (400 MHz, DMSO-d6): δ 11.85 (s, 1H), 8.05 (d, J = 6.1 Hz, 1H), 7.82 (d, J = 8.9 Hz, 2H), 7.69 (d, J = 5.0 Hz, 1H), 7.09 - 7.04 (m, 1H), 6.99 (d, J = 8.9 Hz, 2H), 6.24 (s, 1H), 3.84 (s, 3H), 2.82 (t, J = 6.7 Hz, 2H), 1.85 (t, J = 6.6 Hz, 2H), 1.34 (s, 6H); APCI-MS m/z: 513 [M + H] + ; Anal. calcd. for C25H22O8S2. 2H2O: C, 58.36; H, 4.31. Found: C, 58.37; H, 4.32.
  • 25
  • [ 2766-74-7 ]
  • [ 38226-86-7 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4,8,9,10-tetrahydropyrano[2,3-f]chromen-3-yl 5-chlorothiophene-2-sulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.4% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 26
  • [ 55854-46-1 ]
  • [ 38226-86-7 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4,8,9,10-tetrahydropyrano[2,3-f]chromen-3-yl 5-bromothiophene-2-sulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88.6% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 27
  • [ 38226-86-7 ]
  • methyl 5-(chlorosulfonyl)thiophene-2-carboxylate [ No CAS ]
  • methyl-3-(((5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-4,8,9,10-tetrahydropyrano[2,3-f]chromen-3-yl)oxy)sulfonyl)thiophene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 28
  • C30H30O8 [ No CAS ]
  • [ 38226-86-7 ]
  • 29
  • C30H30O8 [ No CAS ]
  • [ 38226-86-7 ]
  • 30
  • C30H28O7 [ No CAS ]
  • [ 38226-86-7 ]
  • 31
  • C23H24O6 [ No CAS ]
  • [ 38226-86-7 ]
  • 32
  • [ 28610-31-3 ]
  • [ 38226-86-7 ]
  • 33
  • [ 28610-34-6 ]
  • [ 38226-86-7 ]
  • 34
  • [ 28610-35-7 ]
  • [ 77-78-1 ]
  • [ 38226-86-7 ]
YieldReaction ConditionsOperation in experiment
87% The product XIII (48 g, 0.1 mol) was dissolved in acetone (1000 ml), and 3 times the amount of anhydrous potassium carbonate (41.4 g, 0.3 mol) was added thereto, and 1.2 times the amount of dimethyl sulfate (15.1 g, 0.12 mol) was reacted. The liquid was heated to 60 C for 2 h, and then a solvent amount of methanol (1000 ml) was added thereto, and the reflux reaction was continued for 10 h. After completion of the reaction, the reaction solution was evaporated to dryness under reduced pressure, and ice water was added thereto with stirring, and adjusted to pH=6 with 0.5 M hydrochloric acid. Extract three times with dichloromethane (2L × 3), and combine the dichloro layers. Dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure to obtain through a silica gel column (petroleum ether / ethyl acetate = 30/1)) product XIV (32.0 g Icaritin dehydration), Yield 87%
  • 35
  • [ 480-66-0 ]
  • [ 38226-86-7 ]
  • 36
  • [ 90-24-4 ]
  • [ 38226-86-7 ]
  • 37
  • [ 83171-42-0 ]
  • [ 38226-86-7 ]
  • 38
  • C18H16Br2O6 [ No CAS ]
  • [ 38226-86-7 ]
  • 39
  • C18H17BrO6 [ No CAS ]
  • [ 38226-86-7 ]
  • 40
  • C25H22O8 [ No CAS ]
  • [ 38226-86-7 ]
  • 41
  • C25H22O8 [ No CAS ]
  • [ 38226-86-7 ]
  • 42
  • C27H26O10 [ No CAS ]
  • [ 38226-86-7 ]
  • 43
  • C32H34O10 [ No CAS ]
  • [ 38226-86-7 ]
  • 44
  • C32H34O10 [ No CAS ]
  • [ 38226-86-7 ]
  • 45
  • C28H24O7 [ No CAS ]
  • [ 38226-86-7 ]
  • 46
  • [ 118525-40-9 ]
  • [ 38226-86-7 ]
YieldReaction ConditionsOperation in experiment
92% With sulfuric acid; acetic acid; at 90℃; for 6h; 3L 80% glacial acetic acid and 900ml 5mol/LSulfuric acid is placed in an eggplant-shaped bottle,After stirring evenly,0.1 mol of product IX was added thereto,The temperature was raised to 90 C to reflux the reaction.TLC (petroleum ether: dichloromethane: methanol = 40:40:1)Tracking the reaction,The reaction was complete after about 6 hours.The reaction is over,After the reaction solution was cooled to room temperature, the pH was adjusted to 7-8 with a saturated sodium hydrogen carbonate solution.Let stand for an hour,A large amount of yellow solid precipitated,Filtering,The filter cake is washed three times with water and then dried at a low temperature.Product X (34 g, yield 92%).
92% With sulfuric acid; acetic acid; at 90℃; for 6h; (10) Dehydration:Mix 3L 80% glacial acetic acid with 900ml 5mol / LSulfuric acid is placed in an eggplant-shaped bottle,After mixing well,Add 0.1 mol of product IX to it,The temperature was raised to 90 C and the reaction was refluxed.TLC (petroleum ether: dichloromethane: methanol = 40: 40: 1) followed the reaction,The reaction was complete after about 6 hours.The reaction is over,After the reaction solution was cooled to room temperature, its pH was adjusted to 7-8 with a saturated sodium bicarbonate solution.Let stand for an hour,A large amount of yellow solids precipitated,Suction filtration,The filter cake was washed three times with water and dried at low temperature.The product X was obtained (34 g, yield 92%).
  • 47
  • [ 1458-98-6 ]
  • [ 38226-86-7 ]
  • C25H26O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93.3% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; (1)will6g (16.3mmol)Dehydrated icariinversusAfter mixing 80 mL of DMF, 3.38 g (24.5 mmol) of anhydrous potassium carbonate was added thereto.After stirring for 10 minutes, 1.97 mL (19.6 mmol) of 3-bromo-2-methylpropene was slowly added dropwise thereto.Plus,The reaction was carried out at room temperature.(2) TLC (petroleum ether: dichloromethane: methanol = 40:40:1) was followed for the reaction, and the reaction was completed after about 8 hours. After the reaction was completed, the reaction solution was poured into 500 mL of ice water, and the mixture was allowed to stand for one hour after stirring. A large amount of pale yellow solid was precipitated, suction filtered, and the filter cake was washed three times with water and then dried to obtain a crude product of YS-10. The crude product was passed through a silica gel column (petroleum ether: methylene chloride:methanol = 40:40:1) to afford YS-10 (6.4 g, yield 93.3%)
88% (11) Introduction of propylene group: After mixing 0.1 mol of product X with 500 ml of dimethylformamide, 0.15 mol of anhydrous potassium carbonate was added thereto, and after stirring for 10 minutes, a 0.12 mol-fold amount of slowly3-Bromo-2-methylpropene was added and allowed to react at room temperature. TLC (petroleum ether: dichloromethane: methanol = 40: 40: 1) followed the reaction, and the reaction was complete after about 8 hours. After the reaction was completed, the reaction solution was poured into 500 mL of ice water, and the mixture was allowed to stand for one hour after stirring. A large amount of light yellow solid precipitated, filtered with suction, the filter cake was washed with water three times, and dried to obtain a crude YS-10 product. The crude product was passed through a silica gel column (petroleum ether: dichloromethane: methanol = 40: 40: 1) to obtain the product XI, namely YS-10 (37 g, yield 88%).
  • 48
  • [ 64-18-6 ]
  • [ 118525-40-9 ]
  • [ 38226-86-7 ]
YieldReaction ConditionsOperation in experiment
93.3% for 20h;Reflux; A solution of icaritin (3 g, 8.2 mmol) in formic acid (50 mL) was stirred at reflux for 20 h. The reaction solution was then poured into crashed ice. The solid thus collected by filtration to give the title compound (3, 2.8 g, 93.3%) as yellow powder. M.p.221-222 (lit. 223, Akai et al., 1935). 1H NMR (400 MHz, CHCl3) δ = 11.47 (s, 1H, 5-OH), 8.17 (d, J = 8.7 Hz, 2H, Ar-H), 7.03 (d, J = 8.7 Hz, 2H, Ar-H), 6.64 (s, 1H, 3-OH), 6.24 (s, 1H, Ar-H), 3.88 (s, 3H, CH3O), 2.89 (t, J = 6.8 Hz, 2H, CH2-CH2-C(CH3)2), 1.88 (t, J = 6.8 Hz, 2H, CH2-CH2-C(CH3)2), 1.37 (s, 6H, (CH3)2).
  • 55
  • [ 38226-86-7 ]
  • [ 77-78-1 ]
  • [ 55395-01-2 ]
YieldReaction ConditionsOperation in experiment
95% A solution of compound 2 (100 mg, 0.27 mmol) and K2CO3 (75 mg, 0.54 mmol) in acetone (2 ml) was stirred at room temperature for 10 minutes. Dimethyl sulfate (1 equ.) was added dropwise to the suspension within 10 minutes. The reaction was heated to reflux for 6 hours. After cooling to room temperature, the solvent was completely evaporated under reduced pressure. The residue was diluted in dichloromethane and water. The separated organic layer was dried over MgSO4. The solvent was completely evaporated under reduced pressure to obtain compound 3 (95%).
95% A mixture of 3,5-dihydroxy-2-(4-methoxyphenyl)-7,8-(2, 2-dimethyl-2H-pyran)-4H-chromen-4-one (100 mg, 0.27 mmol) and K2CO3 (75 mg, 0.54 mmol) in acetone (2 ml) was stirred at room temperature for 10 min. To the suspension was added dimethyl sulfate (0.026 ml, 1 equ.) drop-wise in 10 min. The reaction was heated to reflux for 6h. After being cooled to room temperature, the solvent was evaporated completely under reduced pressure. The residue was diluted in DCM and water. The separated organic layer was dried over MgSO4. The solvent was evaporated completely under reduced pressure to afford the title compound,5-hydroxy-3-methoxy-2-(4-methoxyphenyl)-7,8-(2,2-dimethyl-2H-pyran)-4H-chromen-4-one (4, 95%). 1H NMR (400 MHz, CDCl3) δ = 12.36 (s, 1H, OH), 8.08 (d, J = 9.1 Hz, 2H, Ar-H), 7.00 (d, J = 9.1 Hz, 2H, Ar-H), 6.21 (s, 1H, Ar-H), 3.85 (d, J = 14.6 Hz, 6H, 2CH3O), 2.83 (t, J = 6.8 Hz, 2H, CH2-CH2-C(CH3)2), 1.84 (t, J = 6.8 Hz, 2H, CH2-CH2-C(CH3)2), 1.34 (s, 6H, (CH3)2). 13C NMR (101 MHz, CDCl3) δ = 178.7 (C=O), 161.5 (C=C), 160.0 (C=C), 159.4 (C=C), 155.1 (C=C), 153.7 (C=C), 139.0 (C=C), 129.9 (2C, C=C), 123.2 (C=C), 114.1 (2C, C=C), 105.7 (C=C), 99.9 (C=C), 99.5 (C=C), 75.9 (C(CH3)2), 60.1 (CH3O), 55.4 (CH3O), 31.7 (CH2-CH2-C(CH3)2), 26.6 (2C, C(CH3)2), 16.3 (CH2-CH2-C(CH3)2).
  • 56
  • [ 64-18-6 ]
  • [ 55929-05-0 ]
  • [ 38226-86-7 ]
YieldReaction ConditionsOperation in experiment
93.3% for 20h;Reflux; A solution of Icaritin (3 g, 8.2 mmol) in formic acid (50 mL) was stirred and refluxed for 20 h. Then the reaction solution was poured into crushed ice. The solid was collected by filtration to obtain the title compound (2, 2.8 g, 93.3%) as a yellow powder.
  • 57
  • [ 38226-86-7 ]
  • C25H27BrO6 [ No CAS ]
  • 58
  • [ 38226-86-7 ]
  • C27H32O6 [ No CAS ]
  • 59
  • [ 38226-86-7 ]
  • C24H25BrO6 [ No CAS ]
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 38226-86-7 ]

Aryls

Chemical Structure| 2034-65-3

[ 2034-65-3 ]

3,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Similarity: 0.90

Chemical Structure| 6665-69-6

[ 6665-69-6 ]

3,5-Dihydroxy-2-phenyl-4H-chromen-4-one

Similarity: 0.90

Chemical Structure| 26964-29-4

[ 26964-29-4 ]

3,5,7-Trimethoxy-2-phenyl-4H-chromen-4-one

Similarity: 0.89

Chemical Structure| 6889-78-7

[ 6889-78-7 ]

3-Hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Similarity: 0.88

Chemical Structure| 14919-49-4

[ 14919-49-4 ]

3-Hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Similarity: 0.88

Ethers

Chemical Structure| 26964-29-4

[ 26964-29-4 ]

3,5,7-Trimethoxy-2-phenyl-4H-chromen-4-one

Similarity: 0.89

Chemical Structure| 6889-78-7

[ 6889-78-7 ]

3-Hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Similarity: 0.88

Chemical Structure| 263365-51-1

[ 263365-51-1 ]

2-(2,4-Dimethoxyphenyl)-3-hydroxy-7-methoxy-4H-chromen-4-one

Similarity: 0.88

Chemical Structure| 7245-02-5

[ 7245-02-5 ]

3-Methoxy-2-phenyl-4H-chromen-4-one

Similarity: 0.87

Chemical Structure| 93176-00-2

[ 93176-00-2 ]

3-Hydroxy-6-methoxy-2-phenyl-4H-chromen-4-one

Similarity: 0.87

Alcohols

Chemical Structure| 2034-65-3

[ 2034-65-3 ]

3,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Similarity: 0.90

Chemical Structure| 6665-69-6

[ 6665-69-6 ]

3,5-Dihydroxy-2-phenyl-4H-chromen-4-one

Similarity: 0.90

Chemical Structure| 6889-78-7

[ 6889-78-7 ]

3-Hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Similarity: 0.88

Chemical Structure| 577-85-5

[ 577-85-5 ]

3-Hydroxy-2-phenyl-4H-chromen-4-one

Similarity: 0.88

Chemical Structure| 14919-49-4

[ 14919-49-4 ]

3-Hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

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Ketones

Chemical Structure| 2034-65-3

[ 2034-65-3 ]

3,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Similarity: 0.90

Chemical Structure| 6665-69-6

[ 6665-69-6 ]

3,5-Dihydroxy-2-phenyl-4H-chromen-4-one

Similarity: 0.90

Chemical Structure| 26964-29-4

[ 26964-29-4 ]

3,5,7-Trimethoxy-2-phenyl-4H-chromen-4-one

Similarity: 0.89

Chemical Structure| 6889-78-7

[ 6889-78-7 ]

3-Hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Similarity: 0.88

Chemical Structure| 14919-49-4

[ 14919-49-4 ]

3-Hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Similarity: 0.88

Related Parent Nucleus of
[ 38226-86-7 ]

Other Aromatic Heterocycles

Chemical Structure| 2034-65-3

[ 2034-65-3 ]

3,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Similarity: 0.90

Chemical Structure| 6665-69-6

[ 6665-69-6 ]

3,5-Dihydroxy-2-phenyl-4H-chromen-4-one

Similarity: 0.90

Chemical Structure| 26964-29-4

[ 26964-29-4 ]

3,5,7-Trimethoxy-2-phenyl-4H-chromen-4-one

Similarity: 0.89

Chemical Structure| 6889-78-7

[ 6889-78-7 ]

3-Hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Similarity: 0.88

Chemical Structure| 14919-49-4

[ 14919-49-4 ]

3-Hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Similarity: 0.88