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Chemical Structure| 6272-26-0
Chemical Structure| 6272-26-0
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Product Details of [ 6272-26-0 ]

CAS No. :6272-26-0 MDL No. :MFCD00068174
Formula : C8H6O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 150.13 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 6272-26-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.23
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) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : 1.12
Log Po/w (WLOGP) : 0.97
Log Po/w (MLOGP) : 0.12
Log Po/w (SILICOS-IT) : 1.69
Consensus Log Po/w : 1.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.88
Solubility : 1.98 mg/ml ; 0.0132 mol/l
Class : Very soluble
Log S (Ali) : -1.69
Solubility : 3.06 mg/ml ; 0.0204 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.98
Solubility : 1.56 mg/ml ; 0.0104 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 6272-26-0 ]

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 [ 6272-26-0 ]

* 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 [ 6272-26-0 ]
  • Downstream synthetic route of [ 6272-26-0 ]

[ 6272-26-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 6272-26-0 ]
  • [ 50551-63-8 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2013, vol. 61, # 10, p. 997 - 1001
  • 2
  • [ 13196-11-7 ]
  • [ 6272-26-0 ]
  • [ 1020947-92-5 ]
  • [ 23681-89-2 ]
YieldReaction ConditionsOperation in experiment
92% With ammonium chloride In tetrahydrofuran; hydrogenchloride; methanol; ethyl acetate Preparation 3
2,3-Dihydro-benzofuran-6-ol
6-Hydroxy-2H-benzofuran-3-one (3 g) was suspended in anhydrous tetrahydrofuran under an argon atmosphere and cooled to 0° C. Lithium aluminium hydride (20 ml of a 1M solution in tetrahydrofuran) was added dropwise over 10 min and the reaction allowed to reach room temperature over 2 hours.
The reaction was cooled to 0° C. and treated dropwise with saturated ammonium chloride solution.
Ethyl acetate (200 ml) was added and the mixture filtered through Celite. The ethyl acetate layer was separated, dried (MgSO4) and evaporated to dryness under reduced pressure.
The resulting mixture of 2,3-dihydro-benzofuran-3,6-diol and benzofuran-6-ol (approximately 1:1 by 250 MHz 1H NMR) was dissolved in a mixture of hydrochloric acid (200 ml, 5M aqueous solution) and methanol (300 ml) and palladium hydroxide (0.5 g) added.
The mixture was stirred under a hydrogen atmosphere for 3 hours then filtered through Celite.
The organics were removed by evaporation under reduced pressure and the resulting solution neutralised with concentrated anmmonia solution.
The product was extracted into dichloromethane.
The dichloromethane solution was dried (MgSO4) and evaporated to dryness under reduced pressure to yield the title compound (2.5 g, 92percent).
1H NMR (250 MHz, CDCl3) δ: 3.11 (2H, t, J=8.4 Hz), 4.57 (2H, t, J=8.4 Hz), 6.27-6.34 (2H, m), 6.92-7.02 (1H, m); m/z (API+): 139.1 (M+3H+).
Reference: [1] Patent: US6465493, 2002, B1,
  • 3
  • [ 6272-26-0 ]
  • [ 23681-89-2 ]
Reference: [1] Journal of the Chemical Society, 1950, p. 3206,3212
[2] Journal of the Chemical Society, 1950, p. 3206,3212
  • 4
  • [ 6272-26-0 ]
  • [ 13196-11-7 ]
  • [ 23681-89-2 ]
Reference: [1] Synthetic Communications, 2014, vol. 44, # 9, p. 1307 - 1313
  • 5
  • [ 6272-26-0 ]
  • [ 74-88-4 ]
  • [ 15832-09-4 ]
YieldReaction ConditionsOperation in experiment
63% With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 6 h; General procedure: To a stirred solution of compound 3 (5 g, 33 mmol) in DMF (20 mL) was added anhydrous potassium carbonate (13.84 g, 100 mmol), iodomethane (3.2 mL, 51 mmol) or 4-methoxybenzyl chloride (5.5 mL, 35 mmol) at 0°C. The reaction mixture was warmed slowly to r.t. and stirred for 6 h. The mixture was poured into water (100 mL) and extracted with ethyl acetate (3 × 100 mL). The combined organic layers were washed with water (2 × 300 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give compounds 5a and 5b.
Reference: [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6360 - 6366
[2] Tetrahedron Asymmetry, 2008, vol. 19, # 7, p. 788 - 795
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3226 - 3230
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4520 - 4523
[5] Patent: WO2005/73224, 2005, A2, . Location in patent: Page/Page column 86-87
[6] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 195 - 208
  • 6
  • [ 6272-26-0 ]
  • [ 77-78-1 ]
  • [ 15832-09-4 ]
YieldReaction ConditionsOperation in experiment
72.84% With potassium carbonate In acetone at 20℃; for 2 h; To a solution of 1-12 (1.5 g, 10 mmol) in acetone (7 ml) was added K2CO3 (2.073 g, 15 mmol), followed by the addition of dimethyl sulfate (1.387 g, 11 mmol). The mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and diluted with water. The aqueous layer was extracted with dichloromethane (3 * 50 ml), dried with Na2SO3, and evaporated to dryness to yield 2-12 as yellow solid which was used without further purification, 72.84percent yield. M.p. 116-118 °C (Lit. m.p. 102-103 °C); 1H NMR (CDCl3, 500 MHz): δ 7.57 (d, J = 8.6 Hz, H4), 6.65 (dd, J1 = 2 Hz, J2 = 8.6 Hz, H5), 6.55 (d, J = 2 Hz, H7), 4.63 (s, 2H), 3.89 (s, 3H). HRMS (TOF-ES) calcd for C9H9O3+ ([M+1]+): 165.0552, found 165.0535.
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 94, p. 195 - 210
[2] Organic and Biomolecular Chemistry, 2008, vol. 6, # 19, p. 3486 - 3496
  • 7
  • [ 6272-26-0 ]
  • [ 588703-29-1 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 3, p. 203 - 206
[2] Patent: WO2014/18748, 2014, A1,
[3] Patent: WO2008/141119, 2008, A2,
  • 8
  • [ 6272-26-0 ]
  • [ 1083168-69-7 ]
Reference: [1] Patent: WO2008/141119, 2008, A2,
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