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[ CAS No. 552-41-0 ] {[proInfo.proName]}

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Chemical Structure| 552-41-0
Chemical Structure| 552-41-0
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Product Details of [ 552-41-0 ]

CAS No. :552-41-0 MDL No. :MFCD00008730
Formula : C9H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :UILPJVPSNHJFIK-UHFFFAOYSA-N
M.W : 166.17 Pubchem ID :11092
Synonyms :
2'-Hydroxy-4'-methoxyacetophenone;Peonol;NSC 401442

Calculated chemistry of [ 552-41-0 ]

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 : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : 1.98
Log Po/w (WLOGP) : 1.6
Log Po/w (MLOGP) : 0.83
Log Po/w (SILICOS-IT) : 1.68
Consensus Log Po/w : 1.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.36
Solubility : 0.733 mg/ml ; 0.00441 mol/l
Class : Soluble
Log S (Ali) : -2.58
Solubility : 0.434 mg/ml ; 0.00261 mol/l
Class : 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 : 1.28

Safety of [ 552-41-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P273-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 552-41-0 ]

* 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 [ 552-41-0 ]
  • Downstream synthetic route of [ 552-41-0 ]

[ 552-41-0 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 552-41-0 ]
  • [ 51864-08-5 ]
  • [ 23999-64-6 ]
YieldReaction ConditionsOperation in experiment
72% With acetylhydroxamic acid; sulfuric acid In acetonitrile at 80℃; for 0.2 h; Microwave irradiation General procedure: 2-Hydroxy acetophenone 4a (1.0 g, 7.4 mmol), acetohydroxamic acid (0.83 g, 11.0 mmol), acetonitrile (3 ml), and conc. H2SO4 (0.2 ml) were taken into a 10 ml pressure tube and subjected to microwave heating (CEM discover, 360 W, 80 °C, 25 psi) for 8 min. Next, the reaction mixture was diluted with ethyl acetate (3 ml) and to this; saturated sodium bicarbonate solution (5 ml) was added drop-wise. The mixture was extracted with ethyl acetate (2 .x. 10 ml) and the combined organic layer was washed with saturated NaCl solution, dried over anhy. Na2SO4, and concentrated under reduced pressure. Purification of the mixture by normal column chromatography (silica gel 60-120 mesh, ethyl acetate/hexane: 1:9) gave benzoxazole 5a (0.67 g, 70percent) in the form of a yellow oil and 2-hydroxy acetophenone oxime 6a (68 mg, 6percent, mp 104-107 °C) in the form of a white powder.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 46, p. 6103 - 6107
  • 2
  • [ 552-41-0 ]
  • [ 23999-64-6 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 17, p. 8657 - 8667
  • 3
  • [ 552-41-0 ]
  • [ 23999-64-6 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 23, p. 6300 - 6303
  • 4
  • [ 552-41-0 ]
  • [ 42327-52-6 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1988, # 6, p. 1570 - 1582
[2] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 11, p. 2098 - 2102
  • 5
  • [ 552-41-0 ]
  • [ 15832-09-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 4, p. 668 - 672
  • 6
  • [ 552-41-0 ]
  • [ 4637-24-5 ]
  • [ 5751-52-0 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: at 100℃; for 0.166667 h;
Stage #2: With hydrogenchloride In dichloromethane; water at 40℃; for 0.5 h;
Example 10A
7-methoxy-4H-1-benzopyran-4-one
1-(2-Hydroxy-4-methoxyphenyl)ethanone (47 g, 283 mmol) was dissolved in N,N-dimethylformamide dimethyl acetal (47 mL, 351 mmol), and the solution was heated to >100° C. in a sand bath for 10 minutes, at which point a solid mass had formed.
The flask was cooled to ambient temperature, and 200 mL of heptanes were added.
The solids were broken up with a spatula and collected by filtration with a frilled funnel.
The solid material was crushed with a pestle and then washed with heptanes.
The solid was then dried on the filter to give about 60 g of the crude intermediate.
This intermediate was dissolved in dichloromethane (1 L) and stirred with 150 mL of concentrated HCl at 40° C. for 30 minutes.
The flask was cooled to ambient temperature, and about 100 mL of water was added.
The layers were separated, and the aqueous layer was extracted with dichloromethane (2*100 mL).
The combined organic extracts were washed with saturated sodium bicarbonate (100 mL) and brine (100 mL) and dried over sodium sulfate.
The mixture was filtered, and the filtrate was concentrated in vacuo to give a solid.
The solid was then precipitated from 500 mL of 1:1 cyclopentyl methyl ether:heptanes to give the title compound (35 g, 70percent yield).
1H NMR (400 MHz, CDCl3) δ ppm 8.11 (d, J=8.9 Hz, 1H), 7.77 (d, J=6.0 Hz, 1H), 6.97 (dd, J=8.9, 2.4 Hz, 1H), 6.84 (d, J=2.4 Hz, 1H), 6.28 (d, J=6.0 Hz, 1H), 3.90 (s, 3H); MS(ESI+) m/z 176.9 (M+H)+.
70%
Stage #1: at 100℃; for 0.166667 h;
Stage #2: With hydrogenchloride In dichloromethane at 40℃; for 0.5 h;
1-(2-Hydroxy-4-methoxyphenyl)ethanone (47 g, 283 mmol) was dissolved in N,N-dimethylformamide dimethyl acetal (47 mL, 351 mmol), and the solution was heated at >100° C. in a sand bath for 10 minutes, at which point a solid mass formed. The flask was cooled to ambient temperature, and 200 mL of heptanes were added. The solids were broken up with a spatula and collected by filtration with a fritted funnel. The solid material was crushed with a pestle and washed with heptanes. The solid was dried on the filter to give about 60 g of the crude intermediate. The intermediate was dissolved in dichloromethane (1 L) and stirred with 150 mL of concentrated HCl at 40° C. for 30 minutes. The flask was cooled to ambient temperature, and about 100 mL of water was added. The layers were separated, and the aqueous layer was extracted with dichloromethane (2×100 mL). The combined organic extracts were washed with saturated sodium bicarbonate (100 mL) and brine (100 mL) and dried over sodium sulfate. The mixture was filtered, and the filtrate was concentrated in vacuo to give a solid. The solid was taken into 500 mL of 1:1 cyclopentyl methyl ether:heptanes and the precipitate was collected to provide the title compound (35 g, 70percent yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.11 (d, J=8.9 Hz, 1H), 7.77 (d, J=6.0 Hz, 1H), 6.97 (dd, J=8.9, 2.4 Hz, 1H), 6.84 (d, J=2.4 Hz, 1H), 6.28 (d, J=6.0 Hz, 1H), 3.90 (s, 3H); MS(ESI+) m/z 176.9 (M+H)+.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 11, p. 2098 - 2102
[2] Patent: US2017/15675, 2017, A1, . Location in patent: Paragraph 0970
[3] Patent: US2017/305891, 2017, A1, . Location in patent: Paragraph 0735
  • 7
  • [ 552-41-0 ]
  • [ 109-94-4 ]
  • [ 5751-52-0 ]
Reference: [1] Chemische Berichte, 1917, vol. 50, p. 917
[2] Journal of Chemical Research, Miniprint, 1988, # 6, p. 1570 - 1582
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3174 - 3186
[4] Chemistry - An Asian Journal, 2015, vol. 10, # 3, p. 540 - 543
  • 8
  • [ 552-41-0 ]
  • [ 5751-52-0 ]
Reference: [1] Chemical Communications, 2012, vol. 48, # 24, p. 2985 - 2987
[2] Tetrahedron, 2012, vol. 68, # 47, p. 9777 - 9787
[3] European Journal of Medicinal Chemistry, 2013, vol. 62, p. 158 - 167
[4] Patent: WO2016/69757, 2016, A1,
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 4, p. 1436 - 1449
[6] Journal of Chemical Sciences, 2018, vol. 130, # 12,
  • 9
  • [ 552-41-0 ]
  • [ 122-51-0 ]
  • [ 5751-52-0 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 1, p. 74 - 77
  • 10
  • [ 552-41-0 ]
  • [ 5751-52-0 ]
  • [ 814257-48-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 11, p. 5293 - 5309
  • 11
  • [ 552-41-0 ]
  • [ 98232-51-0 ]
Reference: [1] Canadian Journal of Chemistry, 2004, vol. 82, # 5, p. 571 - 578
  • 12
  • [ 552-41-0 ]
  • [ 383-63-1 ]
  • [ 578-84-7 ]
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 13, p. 1436 - 1440
  • 13
  • [ 552-41-0 ]
  • [ 578-84-7 ]
Reference: [1] Journal of the Chemical Society, 1951, p. 3235,3238
  • 14
  • [ 552-41-0 ]
  • [ 100-52-7 ]
  • [ 22395-22-8 ]
YieldReaction ConditionsOperation in experiment
88% With pyrrolidine; iodine In dimethyl sulfoxide at 150℃; for 10 h; General procedure: 2'-Hydroxyacetophenone (1 mmol) and substituted aromatic aldehyde (1 mmol) were mixed together along with pyrrolidine (0.5 mmol) and iodine (0.05 mmol) in DMSO solvent (10 mL). The resulting mixture was then heated at 150 °C for the given time. After completion of reaction (monitored by TLC) the reaction mass was allowed to cool and diluted with ethyl acetate (20 mL). Resulting solution was then washed with water and saturated sodium thiosulfate solution followed by drying over anhydrous sodium sulfate and concentrating under reduced pressure to furnish the crude product. The residue obtained was purified by column chromatography using petroleum ether-ethyl acetate as an eluent to afford flavones (3a–r).
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 22, p. 3340 - 3343
[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 45, p. 13302 - 13306[3] Angew. Chem., 2015, vol. 127, # 45, p. 13500 - 13504,5
[4] Organic and Biomolecular Chemistry, 2011, vol. 9, # 20, p. 6930 - 6933
  • 15
  • [ 108-86-1 ]
  • [ 552-41-0 ]
  • [ 201230-82-2 ]
  • [ 22395-22-8 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 40, p. 12595 - 12598
  • 16
  • [ 552-41-0 ]
  • [ 22395-22-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1165 - 1167
[2] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7292 - 7297
[3] Chemical Communications, 2012, vol. 48, # 24, p. 2985 - 2987
[4] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 428 - 432
[5] RSC Advances, 2015, vol. 5, # 124, p. 102191 - 102203
[6] Drug Development Research, 2015, vol. 76, # 8, p. 450 - 462
[7] Patent: CN106083793, 2016, A,
[8] Medicinal Chemistry, 2018, vol. 14, # 2, p. 181 - 199
[9] Molecules, 2018, vol. 23, # 9,
  • 17
  • [ 552-41-0 ]
  • [ 98-88-4 ]
  • [ 22395-22-8 ]
Reference: [1] Synthesis, 1982, # 3, p. 221 - 222
  • 18
  • [ 552-41-0 ]
  • [ 528-48-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 16, p. 7598 - 7616
  • 19
  • [ 552-41-0 ]
  • [ 30992-63-3 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1984, vol. 34, # 8, p. 843 - 849
  • 20
  • [ 552-41-0 ]
  • [ 20784-60-5 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 29, p. 5346 - 5359
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