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Chemical Structure| 498-02-2
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Product Details of [ 498-02-2 ]

CAS No. :498-02-2 MDL No. :MFCD00008747
Formula : C9H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :DFYRUELUNQRZTB-UHFFFAOYSA-N
M.W : 166.17 Pubchem ID :2214
Synonyms :
Acetovanillone;Acetoguaiacone;NSC 209524;NSC 2146
Chemical Name :1-(4-Hydroxy-3-methoxyphenyl)ethanone

Calculated chemistry of [ 498-02-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.15
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.77
Log Po/w (XLOGP3) : 0.51
Log Po/w (WLOGP) : 1.6
Log Po/w (MLOGP) : 0.83
Log Po/w (SILICOS-IT) : 1.68
Consensus Log Po/w : 1.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.43
Solubility : 6.18 mg/ml ; 0.0372 mol/l
Class : Very soluble
Log S (Ali) : -1.06
Solubility : 14.6 mg/ml ; 0.0876 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.28
Solubility : 0.876 mg/ml ; 0.00527 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.36

Safety of [ 498-02-2 ]

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:

Applications of [ 498-02-2 ]

Apocynin (CAS: 498-02-2) can be used in the preparation of Bosutinib (SKI-606) (CAS: 380843-75-4). Bosutinib, a small molecule that inhibits BCR-ABL and src tyrosine kinases, is utilized for treating chronic myelogenous leukemia.

Application In Synthesis of [ 498-02-2 ]

* 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.

  • Upstream synthesis route of [ 498-02-2 ]
  • Downstream synthetic route of [ 498-02-2 ]

[ 498-02-2 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 100-39-0 ]
  • [ 498-02-2 ]
  • [ 1835-11-6 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In N,N-dimethyl-formamide at 40℃; A solution of 4-hydroxy-3- methoxyacetophenone (40 g, 240 mmol), benzyl bromide (31.4 ML, 260 mmol) and potassium carbonate (99.6 g, 360 mmol) in DMF (800 mL) was heated to 40 °C overnight. The solution was cooled to room temperature, poured over ice and the resultant solid was filtered. This material was washed with water and dried to give 1- (4-BENZYLOXY-3- methoxyphenyl) ethanone (61 g, 99 percent).
99% With potassium carbonate In N,N-dimethyl-formamide at 40℃; A solution of 4-hydroxy-3- methoxyacetophenone (40 g, 240 mmol), benzyl bromide (31.4 mL, 260 mmol) and potassium carbonate (99.6 g, 360 mmol) in DMF (800 mL) was heated to 40 °C overnight. The solution was cooled to room temperature, poured over ice and the resultant solid was filtered. This material was washed with water and dried to give l-(4-benzyloxy-3- methoxyphenyl)ethanone (61 g, 99 percent).
99% With potassium carbonate In N,N-dimethyl-formamide at 40℃; A solution of 4-hydroxy-3- methoxyacetophenone (40 g, 240 mmol), benzyl bromide (31.4 ML, 260 mmol) and potassium carbonate (99.6 g, 360 mmol) in DMF (800 mL) was heated to 40 °C overnight. The solution was cooled to room temperature, poured over ice and the resultant solid was filtered. This material was washed with water and dried to give 1- (4-BENZYLOXY-3- methoxyphenyl) ethanone (61 g, 99 percent).
98% With potassium carbonate In acetone for 48 h; Reflux The mixture of 31.62 g (190 mmol) 1-(4-hydroxy-3-methoxy-phenyl)-ethanone, 16.36g (118mmol) potassium carbonate, 0.5g potassium iodide, 400ml acetone and 33.15 g (190 mmol) ml benzyl bromide were refluxed for 2 days. The solventULA-P03071WO21 Application was evaporated, the residue was taken up in 400 ml of water. The precipitate was filtered, washed with 100 ml of sodium carbonate saturated aqueous solution and 2 x100 ml of water, then dried on air to give 47.8 g of product [A]. Yield 98percent.
98% With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 5 h; Step 1) 1-(4-Benzyloxy-3-methoxyphenyl)ethanone
A mixture of 4-hydroxy-3-methoxyacetophenone (40 g, 240 mmol), benzyl bromide (34.1 mL, 260 mmol) and potassium carbonate (50.0 g, 360 mmol) in DMF (800 mL) was stirred at 40° C. for 5 hours.
The reaction was cooled to room temperature and poured into a mixture of ice and water (2000 mL).
The solid was collected by filtration, washed with water and dried in vacuo to give the title compound as a white solid (60.66 g, 98percent).
MS (ESI, pos. ion) m/z: 257.2 [M+1].
1H NMR (400 MHz, CDCl3): δ 7.55-7.54 (d, J=2 Hz, 6H), 7.51-7.49 (dd, J=2.04 Hz, J=8.36 Hz, 1H), 7.45-7.43 (m, 2H), 7.40-7.36 (m, 2H), 7.34-7.32 (d, J=7.16 Hz, 1H), 6.90-6.88 (d, J=8.36 Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H), 2.55 (s, 3H).
97.7%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 0.166667 h;
Stage #2: at 40℃; for 4 h;
6.7g (40 mmol) of D1 are successively 16.6g(120mmol) of potassium carbonate, 30ml DMF was added to a 100ml pear-shaped bottle,After stirring at 40 degrees Celsius for 10 minutes, 5.2 ml (44 mmol) of D2 was added and the reaction was carried out at 40 degrees Celsius for 4 hours. Cool to room temperature, add ice water to the reaction flask, filter, wash,After drying, white powdery solid product D3 12g (39.1 mmol) was obtained with a yield of 97.7percent
96% With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2 h; A 100 mL dry flask was charged with acetovanillone (4.16 g, 0.025 mol) and anhydrous DMF (10 mL). Sodium hydride (1.05 g, 0.0263 mol, 60percent in mineral oil) was added and the reaction mixture was stirred at room temperature followed by the dropwise addition of benzyl bromide (3.1 mL, 0.0263 mol). The reaction was carried out at room temperature for 2 h, then poured into water. Ethyl acetate (150 mL) was used to extract out the compound and the organic layer was washed with water (2x100 mL), brine, dried over sodium sulfate, and concentrated to give the benzyl intermediate (6.21 g, 96percent), which was subsequently used without further purification.
96% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2 h; A 100 mL dry flask was charged with acetovanillone (4.16 g, 0.025 mol) and anhydrous DMF (10 mL). Sodium hydride (1.05 g, 0.0263 mol, 60percent in mineral oil) was added and the reaction mixture was stirred at it followed by the dropwise addition of benzyl bromide (3.1 mL, 0.0263 mol). The reaction was carried out at rt for 2 h, then poured into water. Ethyl acetate (150 mL) was used to extract out the compound and the organic layer was washed with water (2×100 mL), brine, dried over sodium sulfate, and concentrated to give the benzyl intermediate (6.21 g, 96percent), which was subsequently used without further purification.
96.5% With potassium carbonate In N,N-dimethyl-formamide at 40℃; A mixture of 109 (100.0 g, 601.68 mmol), benzyl bromide (79.0 mL, 649.81 mmol) and potassium carbonate (249.0 g, 1.8 mol) in N,N-dimethylformamide (2000 mL) was heated to 40° C. overnight. The solution was cooled to room temperature, poured into ice water (1500 mL) and stirred for 1 h. The resultant solid was filtered and washed by H2O (2×500 mL), dried to give 110 (148.8 g, yield=96.5percent) as a white solid.
95.31% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.25 h; Microwave irradiation 0.830 g (5 mmol) of acetovanillone (1), 1.026 g (6 mmol) of benzyl bromide, 0.828 g (6 mmol) of powdered potassium carbonate, and 10 mL of dimethyl formamide were added to a microwave accelerated reaction system (Milstone Ethos A, Italy).
After reacting for 15 min at 80 °C, the reaction mixture was poured into 30 mL of water and white precipitates appeared.
The precipitate was collected and washed with distilled water several times and then dried at room temperature under vacuum to give compound 2 in 95.31percent yield. 1H NMR (400 MHz, CDCl3): δ 2.57 (s, 3H, CH3), 3.95 (s, 3H, OCH3), 5.25 (s, 2H, CH2), 6.90-7.57 (m, 8H, aromatics); 13C NMR (100 MHz, CDCl3): δ 26.3 (CH3), 56.1 (OCH3), 70.8 (CH2), 112.2-152.3 (C, aromatics), 197.0 (C=O).
91%
Stage #1: With potassium carbonate In acetone at 20℃; for 0.5 h;
Stage #2: at 60℃; for 21 h;
In a 500 ml flask Solanaceae, 4-hydroxy-3-methoxy aminoacetophenone of 20. 8g (125mmol, 1. 0eq. ), 220 ml monohydroxyacetone, potassium carbonate 17. 4g (126mmol, 1. 0eq. ) Put, 30 minutes after stirring at room temperature, a benzyl bromide 18 ml (151mmol, 1. 2eq. ) Addition, reflux in time at 60 °C 21. After condensing, the purified water and adding 200 ml, extracted with chloroform (100 ml × 3), magnesium sulfate waterlessly org. layer by drying, filtering, concentrated, recrystallization (ethyl acetate 50 ml, Phenylbicyclohexane 1 ml, 60 °C), suction filtration, vacuum drying, a first crystal is obtained. Concentrating somas, recrystallization (ethyl acetate 5 ml, 60 °C), suction filtration, vacuum drying, a second crystal is obtained. The white crystal (compd. (I1)), yielding: 29. 2g (114mmol, 91percent)is obtained.
70.3% With potassium carbonate; potassium iodide In acetonitrile for 24 h; Reflux; Inert atmosphere To a solution of acetovanillone (33) (4.70 g, 28.3 mmol) in MeCN (60 mL) was added K2CO3 (8.05 g, 58.3 mmol) and KI (0.20 g, 1.2 mmol).
The mixture was stirred under N2 atmosphere and benzyl bromide (34) (4.0 mL, 34 mmol) was added dropwise.
The reaction mixture was reflux for 24 h and then cooled to 25° C., then resulting precipitate was filtered off.
The filtrate was evaporated and purified by column chromatography (SiO2, n-hexane: CH2Cl2=1:2) to give 30.
White solid; yield: 70.3percent; mp 87-88° C.; 1H-NMR (CDCl3. 200 MHz): δ 2.51 (s, 3H), 3.91 (s, 3H), 5.20 (s, 2H), 6.86 (d, J=8.2 Hz, 1H), 7.21-7.55 (m, 7H); 13C-NMR (CDCl3, 50 MHz): δ 26.19, 56.05, 70.79, 110.53, 112.13, 123.07, 127.18, 128.10, 128.68, 130.72, 136.28, 149.49, 152.41, 196.80; Anal. calcd for C16H16O3: C, 74.98; H, 6.29. Found: C, 75.02; H, 6.25.
594.5 g
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25 h;
Stage #2: at 20℃; for 4 h;
At room temperature, 400.0 g (2.41 mol) of 3-methoxy-4-hydroxyacetophenone II was added to 2 L of DMF. 997.7 g (7.23 mol) of anhydrous potassium carbonate was added. After stirring for 15 min, a solution of 430.2 g (2.53 mol) of benzyl bromide was added dropwise. Drop finished. Stir at room temperature for 4 h. The reaction solution was poured into 10 L of ice water. Filter. Obtained 594.5 g of a white solid.

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  • 2
  • [ 77-78-1 ]
  • [ 498-02-2 ]
  • [ 1835-11-6 ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6 h; Compound 18 (8.3 g, 50 mmol) was dissolved in DMF (50 mL) and then anhydrous K2CO3 (2.5 g) and benzyl chloride (6.3 g, 50 mmol) were added. The reaction mixture was stirred at 80 °C for 6 h. The resulting crude was dissolved in H2O and extracted with EtOAc and then was purified by silica gel column chromatography to obtain 19 (12 g, 94percent) as a white powder, m.p. 82-84 °C; IR (neat) νmax 2873, 1670, 1585, 1512, 1458, 115, 1350, 1276, 1215, 1145, 1076, 991, 871, 798, 748 cm-1; 1HNMR (300 MHz, CDCl3) δ 7.57-7.33 (7H, m), 6.90 (1H, d, J = 9.0 Hz), 5.23 (2H, s), 3.95 (3H, s), 2.55 (3H, s); 13CNMR (75 MHz, CDCl3) δ 196.6, 152.2, 149.3, 136.1, 130.5, 128.5, 127.9, 127.0, 122.9, 111.9, 110.3, 70.6, 55.8, 26.0; EIMS m/z (rel. int.): 256 [M]+ (39), 92 (26), 91 (100), 65 (24); HREIMS calcd for C16H16O3 [M]+ 256.1099, found 256.1096.
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 48, p. 371 - 378
  • 3
  • [ 100-44-7 ]
  • [ 498-02-2 ]
  • [ 1835-11-6 ]
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  • 4
  • [ 1397255-02-5 ]
  • [ 23795-02-0 ]
  • [ 498-02-2 ]
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  • 5
  • [ 1131-62-0 ]
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  • [ 498-02-2 ]
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  • 6
  • [ 613-70-7 ]
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  • [ 498-02-2 ]
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  • 7
  • [ 64-19-7 ]
  • [ 498-02-2 ]
  • [ 54771-60-7 ]
YieldReaction ConditionsOperation in experiment
100% With pyridine In tetrahydrofuran at 20℃; for 3 h; Reference Example 1. Preparat ion of intermedi ate (1) : 4-acetyl-2- methoxyphenyl acetate ( 1)<328>1<329><330> As shown in the above-descr ibed react ion formula, acetovani l lone(500mg , 3mM) di ssolved in 20 ml of THF was mixed wi th 0.5 ml of pyr idine and 0.6 ml of anhydrous acet ic acid. The mixture was st i rred for 3 hours at room <n="38"/>temperature. The resulting product was recovered with the extraction with diethylether and dried with anhydrous magnesium sulfate to remove remaining solvent. The remaining residue was performed to Silica gel column chromatography with a mobile phase (n-hexane:ethylacetate=4:l) to obtain white solid type of 4-acetyl-2-methoxyρhenyl acetate (1 ; 625mg).<331> <332> m.p.: 58.7 °C ;<333> 1H NMR (CDCl3) : δ ppm 7.60 (d, 1 H1 J = 1.8 Hz , H-3), 7.55 (dd, 1 H, J = 1.8, 8.2 Hz, H-5), 7.12 (d, 1 H, J = 8.2 Hz, H-6), 3.89 (s, 3 H, OCH3), 2.59 (s, 3 H, OCOCH3), 2.33 (s, 3 H, COCH3).
Reference: [1] Patent: WO2008/41826, 2008, A1, . Location in patent: Page/Page column 17; 35-36
  • 8
  • [ 108-24-7 ]
  • [ 498-02-2 ]
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[6] Patent: US2010/197685, 2010, A1, . Location in patent: Page/Page column 12-13
  • 9
  • [ 108-24-7 ]
  • [ 24332-96-5 ]
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  • [ 7404-35-5 ]
  • [ 141243-23-4 ]
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  • 10
  • [ 108-24-7 ]
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  • 11
  • [ 498-02-2 ]
  • [ 418759-58-7 ]
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  • 12
  • [ 498-02-2 ]
  • [ 175281-76-2 ]
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  • 13
  • [ 498-02-2 ]
  • [ 380844-49-5 ]
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  • 14
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  • [ 205448-31-3 ]
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