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[ CAS No. 10242-08-7 ] {[proInfo.proName]}

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Chemical Structure| 10242-08-7
Chemical Structure| 10242-08-7
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Product Details of [ 10242-08-7 ]

CAS No. :10242-08-7 MDL No. :MFCD00079771
Formula : C10H8O4 Boiling Point : -
Linear Structure Formula :- InChI Key :XZELWEMGWISCTP-UHFFFAOYSA-N
M.W : 192.17 Pubchem ID :288638
Synonyms :

Calculated chemistry of [ 10242-08-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.67
TPSA : 59.67 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) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.7
Log Po/w (XLOGP3) : 2.38
Log Po/w (WLOGP) : 2.14
Log Po/w (MLOGP) : 0.8
Log Po/w (SILICOS-IT) : 1.74
Consensus Log Po/w : 1.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.257 mg/ml ; 0.00133 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.102 mg/ml ; 0.000532 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.79
Solubility : 0.311 mg/ml ; 0.00162 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.2

Safety of [ 10242-08-7 ]

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 [ 10242-08-7 ]

* 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.

  • Upstream synthesis route of [ 10242-08-7 ]
  • Downstream synthetic route of [ 10242-08-7 ]

[ 10242-08-7 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 50551-56-9 ]
  • [ 10242-08-7 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydroxide In 1,4-dioxane at 20℃; for 2 h; Under ice-cooling,2-hydroxy-5-methoxybenzaldehyde (3.0g, 20mmol) and anhydrous K2CO3 (3.3g,23.4mmol) (50ml) was dissolved in DMF, was slowly added dropwise ethylbromoacetate (3.3g, 20mmol). After dropping Bi, 0 ° C was stirred for 30min,then at 60 ° C in an oil bath, the reaction 12h. The reaction solution waspoured into ice water, over Filtered, the solid was dissolved in chloroform,dried over anhydrous Na2SO4, filtered, and spin dry the solvent, by silica gelcolumn chromatography, To give 3.24 g of a yellow solid (75percent yield), which was dissolved indioxane (30ml) was added 1N hydrogen Sodium hydroxide solution (15ml), stirredat room temperature 2h, the dioxane was evaporated to dryness, the residualliquid was poured into ice water, washed with diethyl Washed with methylenechloride, adjusting the PH value to 2, the solid was collected by filtration 2.68g (92percent yield), whichwas dissolved in methylene Dioxane (50ml), was added DIC (1.51g, 11.98mmol),after stirring at room temperature 1h, was added DMAP (0.24g, 1.96 mmol) anddimethyl hydroxyethyl phosphonate (1.84g, 10.95mmol), heated to reflux after6h, water and saturated brine The reaction solution was washed with water,dried over anhydrous magnesium sulfate, filtered and evaporated to dryness,ethyl acetate - petroleum ether system recrystallized To (dimethoxyphosphoryl)ethyl 5-methoxybenzofuran-2-carboxylate 3.67g (77percent yield), which was Was dissolved indichloromethane (50ml), was added trimethylsilyl bromide (9.85g, 64.8mmol) atroom temperature was stirred for 3h, with Quench with methanol, evaporated todryness to give the product 5-methoxy-benzofuran-2-carboxylic acid ethyl esterphosphono 2.38 g (yield, 74percent).
Reference: [1] Patent: CN103130705, 2016, B, . Location in patent: Paragraph 0201-0203
[2] Journal of Medicinal Chemistry, 1984, vol. 27, # 5, p. 570 - 576
[3] Journal of Materials Chemistry, 2001, vol. 11, # 11, p. 2759 - 2772
[4] Patent: US2009/29976, 2009, A1, . Location in patent: Page/Page column 18
  • 2
  • [ 672-13-9 ]
  • [ 10242-08-7 ]
Reference: [1] Journal of Materials Chemistry, 2001, vol. 11, # 11, p. 2759 - 2772
[2] Journal of Medicinal Chemistry, 1984, vol. 27, # 5, p. 570 - 576
[3] Patent: CN103130705, 2016, B,
[4] Angewandte Chemie - International Edition, 2018, vol. 57, # 21, p. 6242 - 6246[5] Angew. Chem., 2018, vol. 130, p. 6350 - 6354,5
  • 3
  • [ 672-13-9 ]
  • [ 685-87-0 ]
  • [ 10242-08-7 ]
Reference: [1] Biochemical Journal, 1957, vol. 66, p. 188,191
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 872
  • 4
  • [ 1447608-52-7 ]
  • [ 10242-08-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 21, p. 6242 - 6246[2] Angew. Chem., 2018, vol. 130, p. 6350 - 6354,5
  • 5
  • [ 10242-08-7 ]
  • [ 56172-36-2 ]
YieldReaction ConditionsOperation in experiment
100% With boron tribromide In dichloromethane at -78 - 20℃; for 4 h; Step 1:
Preparation of 2-carboxy-5-hydroxybenzofuran.
2-Carboxy-5-methoxybenzofuran (1.0 g, 5.2 mmol) was dissolved in anhydrous dichloromethane (25 ml) and cooled to -78° C. A 1 M solution of borontribromide (15.6 ml) in dichloromethane was added slowly.
The reaction mixture was allowed to warm to ambient temperature under an atmosphere of nitrogen, and stirred 4 hours.
The solution was quenched with aqueous ammonium chloride (20 ml) and extracted with ethyl acetate.
The aqueous layer was washed with water and dried over sodium sulfate. 0.9 g (100percent) of crude product was obtained. 1H NMR(CD3OD) δ=6.84 (dd, 1H), 6.95 (d, 1H), 7.17 (s, 1H), 7.32 (d, 1H).
Reference: [1] Patent: US2005/26969, 2005, A1, . Location in patent: Page/Page column 12
[2] Patent: WO2008/157270, 2008, A1, . Location in patent: Page/Page column 74-75
  • 6
  • [ 10242-08-7 ]
  • [ 93885-41-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 5, p. 570 - 576
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