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[ CAS No. 67604-48-2 ] {[proInfo.proName]}

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Chemical Structure| 67604-48-2
Chemical Structure| 67604-48-2
Structure of 67604-48-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 67604-48-2 ]

CAS No. :67604-48-2 MDL No. :
Formula : C15H12O5 Boiling Point : -
Linear Structure Formula :- InChI Key :FTVWIRXFELQLPI-UHFFFAOYSA-N
M.W : 272.25 Pubchem ID :932
Synonyms :
S-Dihydrogenistein;Salipurol;NSC 34875;NSC 11855;Naringenin

Calculated chemistry of [ 67604-48-2 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.13
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 71.57
TPSA : 86.99 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 2.52
Log Po/w (WLOGP) : 2.19
Log Po/w (MLOGP) : 0.71
Log Po/w (SILICOS-IT) : 2.05
Consensus Log Po/w : 1.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.49
Solubility : 0.0874 mg/ml ; 0.000321 mol/l
Class : Soluble
Log S (Ali) : -3.99
Solubility : 0.0277 mg/ml ; 0.000102 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.42
Solubility : 0.104 mg/ml ; 0.000382 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.01

Safety of [ 67604-48-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 67604-48-2 ]

* 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 [ 67604-48-2 ]

[ 67604-48-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 480-41-1 ]
  • [ 520-36-5 ]
YieldReaction ConditionsOperation in experiment
95% With sulfuric acid; iodine In dimethyl sulfoxide at 100℃; for 1.5h;
93% With pyridine; iodine for 4h; Heating;
66% With pyridine; iodine at 95℃; for 5h; Apigenin: Apigenin: A solution of naringenin (5.0 g, 18 mmol) and iodine (5.0 g,19 mmol) in pyridine (50 mL) was heated to 95 °C for 5 h. The mixturewas poured into ice water. The resulting precipitate was filtered,and then washed with water, dilute hydrochloric acid and saturatedsodium thiosulfate. Recrystallisation of the dried residue from ethanolafforded apigenin: 3.20 g; 66%; m.p. 345-350 °C (lit.23 344-346 °C).
65% With indium(III) bromide; silica gel at 130 - 140℃; for 2h;
With ethanol; iodine; sodium acetate
With sulfuric acid; iodine; dimethyl sulfoxide at 100℃; for 0.5h; Yield given;
25.8 g With trifluoroacetic anhydride; potassium iodide In dimethyl sulfoxide; N,N-dimethyl-formamide at 80℃; for 8h; 1-5 Example 1 In a clean and dry 500L reaction bottle, feed naringenin (content greater than 95%) 30g, DMF 100g, stir to dissolve, add 0.2g potassium iodide, and raise the temperature to 80 C, the mixed solution of 30 g of dimethyl sulfoxide and 0.3 g of trifluoroacetic anhydride was added dropwise, and the drop was completed in about 2 hours. After the dropwise addition, the heat preservation reaction is started, and the raw material is controlled in the liquid phase for 6 hours, and the raw material is less than 2%, and the reaction is stopped. After dropping to room temperature, ammonia water was added dropwise, and the reaction was continued for 1 h. Filtration, the filtrate was recovered under reduced pressure to obtain a black oil. Add 300g of 5% hydrochloric acid solution, continue to reflux for half an hour, filter by heat, and continue to wash the filter cake with hot water until neutral, to obtain crude apigenin. DMF was added to dissolve and clarify the crude product, and the solvent was recovered to one-half. Ethanol was added to beat, cooled, filtered, and dried to obtain light yellow apigenin 25.8g, with a content of 98%.
With pyridine; iodine at 90℃; for 24h; 4',5,7-Triacetoxyflavone (apigenin 4',5,7-triacetate, 1a) Naringenin (2f) was prepared from 2e according to the reported procedure8. To a solution of 2f (1.36 g, 5.00 mmol) in pyridine (7.5 mL) was added iodine (1.40 g, 5.51 mmol), and the mixture was stirred for 24 h at 90oC. To the mixture were added acetic anhydride (10 mL) and catalytic amount of 4-(N,N-dimethylamino)pyridine (DMAP), and further stirred for 6 h at 80oC. After cooling, the mixture was concentrated in vacuo and the residue was diluted with water. The precipitates were collected by filtration and dissolved in CHCl3. The resulting suspension was filtered to remove insoluble materials through a pad of Celite and washed with CHCl3. The filtrate and washings were combined and concentrated in vacuo. The residue was purified by silica gel column chromatography (50 g). Elution with hexane/CHCl3 (3:1 to 1:1) furnished 1a as a colorless solid (1.67 g, 80%).

  • 2
  • [ 480-41-1 ]
  • [ 480-41-1 ]
  • [ 480-41-1 ]
YieldReaction ConditionsOperation in experiment
With carbon dioxide; In methanol; at 20℃; under 90009.0 Torr;Resolution of racemate; The analysis was performed using a 4.6 mm 100 mm ChiralpakAD-H column (Chiral Technologies, West Chester, PA, USA)with 3 mm particle and 1000 A pore sizes. The flow rate was 4.0 mL/min with the outlet back pressure set to 120 bars. The sample wasdissolved in methanol at a concentration of 1 mg/1 mL, and theinjection volume was 2 mL. The composition of the mobile phaseconsisted of carbon dioxide and methanol with a gradient profile of10e60% methanol in 3.7 min. The column temperature was ambient room temperature. The MSD positive scan range was100e800 amu with source temperature at 450 C vaporization and325 C drying gas at a flow rate of 7 L/min. The capillary voltagewas2500 V with a corona current of 5 mA. Purification was performedusing a 21.1 mm 250 mm Chiralpak AD-H column (Chiral Technologies,West Chester, PA, USA) with 5 mm particle and 1000 Apore sizes. The flow rate was 70 mL/min with the outlet backpressure set to 150 bars. The sample was dissolved in methanol at aconcentration of 65 mg/mL, and the injection volume was 1.5 mL,stacked in 3.25-min intervals. The mobile phase consisted of carbondioxide and methanol at 50% (v/v), and the column temperaturewas set to 40 C.
  • 3
  • [ 520-36-5 ]
  • [ 480-41-1 ]
YieldReaction ConditionsOperation in experiment
91% With palladium 10% on activated carbon; hydrogen at 20℃; General procedure for the preparation of compounds 1-3 and 8 General procedure: To a solution of flavonoid (4 mmol) in dry tetrahydrofuran (15 mL) or N,N-dimethylformamide (15 mL) was added 20-400 mgof 10% Pd/C in a hydrogen atmosphere at room temperature. The resulted mixture was stirred for 3-6 h, and the catalyst was removed by filtration. Concentration under reduced pressure furnished a residue, which was purified over a silica gel column eluting with EtOAc-petroleum ether.
25% With palladium 10% on activated carbon; hydrogen
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