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[ CAS No. 53936-56-4 ] {[proInfo.proName]}

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Chemical Structure| 53936-56-4
Chemical Structure| 53936-56-4
Structure of 53936-56-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 53936-56-4 ]

CAS No. :53936-56-4 MDL No. :MFCD09970981
Formula : C11H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :GFBCWCDNXDKFRH-UHFFFAOYSA-N
M.W : 194.23 Pubchem ID :11745519
Synonyms :

Calculated chemistry of [ 53936-56-4 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.16
TPSA : 38.69 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) : 2.07
Log Po/w (XLOGP3) : 2.4
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 1.53
Log Po/w (SILICOS-IT) : 2.07
Consensus Log Po/w : 2.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.74
Solubility : 0.352 mg/ml ; 0.00181 mol/l
Class : Soluble
Log S (Ali) : -2.85
Solubility : 0.272 mg/ml ; 0.0014 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.46
Solubility : 0.667 mg/ml ; 0.00344 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.86

Safety of [ 53936-56-4 ]

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 [ 53936-56-4 ]

* 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 [ 53936-56-4 ]
  • Downstream synthetic route of [ 53936-56-4 ]

[ 53936-56-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 110-87-2 ]
  • [ 123-31-9 ]
  • [ 53936-56-4 ]
YieldReaction ConditionsOperation in experiment
52.7% With pyridinium p-toluenesulfonate In dichloromethane at 10 - 25℃; for 16 h; Inert atmosphere Under a nitrogen atmosphere, the compound (T-1) (19.1g, 227.0mmol) was dissolved in a p-toluenesulfonic acid pyridinium (PPTS) (5.7g, 22.7mmol) in dichloromethane (200ml) . After cooling to 10°C , the compound (T-7) (25.0g, 227.0mmol) was dropped slowly dichloromethane (100ml) solution. The reaction mixture is allowed to warm to 25°C. After stirring for 16 hours, poured into water (500ml). After the aqueous layer was extracted with dichloromethane, and the combined organic layer, water, saturated sodium hydrogen carbonate aqueous solution was washed successively with saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, the residue was purified by silica gel chromatography (volume ratio, toluene: ethyl acetate = 5: 1) to give the compound (T-8) (23.2g, 119.7mmol, 52.7 percent) was obtained.
43% Inert atmosphere Example 17 Step 1; To a reaction flask containing a mixture of hydroquinone (110 g, 1.0 mol), pTSA (9.5 g, 0.05 mol), and 1 L of diethyl ether was added DHP (84 g, 1.0 mol) over a period of 30 min with stirring under a nitrogen atmosphere. After stirring overnight with nitrogen bubbling, the solution was extracted twice with nitrogen-purged solutions of 22.5 g of NaOH in 300 mL of water (total: 1.12 mol). The combined aqueous NaOH solutions were extracted with 300 mL of diethyl ether and cooled to 0° C. with an ice bath. Sodium bicarbonate (5.0 g) was added, and the stirred solution was slowly acidified with 64 mL of acetic acid (1.12 mol). The resulting mixture was stored at -18° C. overnight and then allowed to warm up to 0° C. The precipitated product was washed three times with 300 mL of water and dried under vacuum. The yield was 84 g (43percent). NMR showed that the product had a structure consistent with 4-(tetrahydro-2H-pyran-2-yloxy) phenol.
Reference: [1] Canadian Journal of Chemistry, 2006, vol. 84, # 9, p. 1174 - 1179
[2] Patent: JP5978938, 2016, B2, . Location in patent: Paragraph 0149; 0154
[3] Journal of Materials Chemistry, 2012, vol. 22, # 48, p. 25011 - 25018
[4] Patent: US2009/326186, 2009, A1, . Location in patent: Page/Page column 64
[5] Angewandte Chemie - International Edition, 2013, vol. 52, # 16, p. 4356 - 4360[6] Angew. Chem., 2013, vol. 125, # 16, p. 4452 - 4456
[7] Patent: EP1990339, 2008, A1, . Location in patent: Page/Page column 13-14; 16-17
[8] Patent: EP1405850, 2004, A1, . Location in patent: Page 8; 13-14
[9] Journal of the Iranian Chemical Society, 2016, vol. 13, # 9, p. 1699 - 1712
  • 2
  • [ 53936-79-1 ]
  • [ 53936-56-4 ]
YieldReaction ConditionsOperation in experiment
100% With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃; for 3 h; Autoclave To a 1-liter autoclave, 56.3 g (198 mmol) of the compound (9-2), 2.8 g of a catalyst (5percent Pd/C), and 250 ml of ethanol were added. The resulting mixture was reacted at room temperature for 3 hours while the hydrogen pressure was maintained to be 0.4 MPa. After the catalyst had been removed by filtration, vacuum concentration was performed. Hereby, 38.5 g of the compound (9-3) was prepared (quantitative)
82% With aluminum oxide; hydrogen In ethyl acetate at 20℃; According to this procedure several other bases were tested (see table).
80% With hydrogen; calcium carbonate In ethyl acetate at 20℃; Example 2; Step 2; To a stirred solution of the product (30 g, 0.105 mol), calcium carbonate (2.79 g, 0.027 mol) and ethyl acetate (120 ml) was added palladium on carbon (3.6 g). The mixture was stirred at ambient temperature under hydrogen pressure until uptake of hydrogen ceased. The mixture was filtered and washed with ethyl acetate. The solvent was distilled off in vacuum. The evaporation residue was dissolved in alcohol (36 ml) and the product precipitated by the addition of water (144 ml). The slurry was cooled to 00C and stirred vigorously for 2 h. Precipitated product was filtered and washed with water, dried in vacuum to give 80percent of Deoxyarbutin with a purity of 99.8percent (area by HPLC).
80% With hydrogen; sodium carbonate In isopropyl alcohol at 20℃; According to this procedure several other bases were tested (see table).
80% With hydrogen; calcium carbonate In ethanol; ethyl acetate at 20℃; According to this procedure several other bases were tested (see table).
78% With hydrogen; calcium carbonate In ethanol at 20℃; According to this procedure several other bases were tested (see table).
77% With hydrogen; calcium carbonate In isopropyl alcohol at 20℃; According to this procedure several other bases were tested (see table).
4.1 g With pyridine; 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; ethanol at 50℃; for 8 h; In a pressure-resistant container, 6.7 g of the compound represented by the formula (I-1-4) 70 mL of tetrahydrofuran, 20 mL of ethanol, 10 mL of pyridine, 0.7 g of 5percent palladium carbon (containing 60percent of water) was added, 0.5 MPa, And the mixture was heated and stirred at 50 ° C. for 8 hours. The palladium was removed by filtration and the solvent was distilled off. Dissolve in ethyl acetate, add 1percent hydrochloric acid, Washed sequentially with water and brine. Purification was carried out by column chromatography (alumina, ethyl acetate) 4.1 g of a compound represented by the formula (I-1-5) was obtained.

Reference: [1] Patent: US2017/260150, 2017, A1, . Location in patent: Paragraph 0146; 0148
[2] Patent: WO2006/134124, 2006, A1, . Location in patent: Page/Page column 7
[3] Patent: WO2006/134124, 2006, A1, . Location in patent: Page/Page column 7
[4] Patent: WO2006/134124, 2006, A1, . Location in patent: Page/Page column 7
[5] Patent: WO2006/134124, 2006, A1, . Location in patent: Page/Page column 7
[6] Patent: WO2006/134124, 2006, A1, . Location in patent: Page/Page column 7
[7] Patent: WO2006/134124, 2006, A1, . Location in patent: Page/Page column 7
[8] Patent: JP2018/35126, 2018, A, . Location in patent: Paragraph 0153; 0156
  • 3
  • [ 134142-87-3 ]
  • [ 53936-56-4 ]
Reference: [1] New Journal of Chemistry, 2002, vol. 26, # 10, p. 1273 - 1276
  • 4
  • [ 36637-44-2 ]
  • [ 53936-56-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 13, p. 3353 - 3357[2] Angew. Chem., 2014, vol. 126, # 13, p. 3421 - 3425,5
  • 5
  • [ 110-87-2 ]
  • [ 123-31-9 ]
  • [ 2139-44-8 ]
  • [ 53936-56-4 ]
Reference: [1] Canadian Journal of Chemistry, 2005, vol. 83, # 8, p. 1120 - 1123
[2] Journal of Organometallic Chemistry, 2005, vol. 690, # 17, p. 3865 - 3877
  • 6
  • [ 103-16-2 ]
  • [ 53936-56-4 ]
Reference: [1] Patent: US2017/260150, 2017, A1,
[2] Patent: JP2018/35126, 2018, A,
  • 7
  • [ 110-87-2 ]
  • [ 53936-56-4 ]
Reference: [1] Patent: US2017/260150, 2017, A1,
[2] Patent: JP2018/35126, 2018, A,
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