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[ CAS No. 13494-10-5 ] {[proInfo.proName]}

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Chemical Structure| 13494-10-5
Chemical Structure| 13494-10-5
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Product Details of [ 13494-10-5 ]

CAS No. :13494-10-5 MDL No. :MFCD03424392
Formula : C8H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :HEJLFBLJYFSKCE-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :6429110
Synonyms :

Calculated chemistry of [ 13494-10-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.68
TPSA : 57.53 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 : Yes
Log Kp (skin permeation) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 1.56
Log Po/w (WLOGP) : 1.3
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : 1.19
Consensus Log Po/w : 1.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.2 mg/ml ; 0.00787 mol/l
Class : Soluble
Log S (Ali) : -2.38
Solubility : 0.637 mg/ml ; 0.00419 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.57
Solubility : 4.13 mg/ml ; 0.0272 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.04

Safety of [ 13494-10-5 ]

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

Application In Synthesis of [ 13494-10-5 ]

* 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 [ 13494-10-5 ]
  • Downstream synthetic route of [ 13494-10-5 ]

[ 13494-10-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 38480-94-3 ]
  • [ 13494-10-5 ]
YieldReaction ConditionsOperation in experiment
76% With boron tribromide In methanol; dichloromethane; ethyl acetate 18G 2',3'-Dihydroxyacetophenone
A solution of 2',3'-dimethoxyacetophenone (4.85 g, 26.9 mmol) in dichloromethane (100 ml) was added at -70° C. with a 1M boron tribromide solution in dichloromethane (68 ml).
The mixture was left to cool, keeping stirring for 2.5 hours at room temperature, then added with methanol (70 ml), left under stirring for 1 h, thereafter evaporated to dryness.
The residue was dissolved in ethyl acetate (250 ml), washed with 2percent NaHCO3 (1*30 ml), dried and the solvent was evaporated off, to obtain a crude which was purified by crystallization in methanol, thereby obtaining 3.10 g of the title compound as a yellow solid (76percent yield).
1 H N.M.R. (300 MHz, CDCl3) δ ppm: 2.61 (s, 3H); 7.05-6.77 (t, 1H); 7.02 (dd, 1H); 7.36 (dd, 1H).
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 1, p. 183 - 192
[2] Patent: US5990142, 1999, A,
[3] Chemische Berichte, 1913, vol. 46, p. 4019
[4] Chemische Berichte, 1913, vol. 46, p. 4019
[5] Journal of the American Chemical Society, 2005, vol. 127, # 29, p. 10371 - 10387
  • 2
  • [ 120-80-9 ]
  • [ 64-19-7 ]
  • [ 13494-10-5 ]
YieldReaction ConditionsOperation in experiment
10.4% With boron trifluoride diethyl etherate In diethyl ether at 25℃; for 0.025 h; Microwave irradiation To a solution of 1,2-dihydroxybenzene (28)(2.0 g, 18.2 mmol) in AcOH (1.3 g, 21.7 mmol) was added boron trifluoride diethyl ether (98percent in Et2O, 2 mL).
The mixture was reacted under microwave irradiation (300 W) for 1.5 min and then cooled to 25° C.
The reaction mixture was dissolved in dichoromethane (10 mL) and H2O (about 20 mL).
The organic lay was washed with 10percent NaHCO3 and then with water, dried over MgSO4 and concentrated.
The crude was purified by column chromatography (SiO2, CH2Cl2) to give 30.
Yellow solid; yield: 10.4percent; mp 76-77° C.; 1H-NMR (CDCl3,200 MHz): δ 2.58 (s, 3H), 5.79 (s, 1H), 6.79 (t, J=8.0 Hz, 1H), 7.10 (d, J=8.0 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 12.45 (s, 1H); 13C-NMR (CDCl3, 50 MHz): δ 26.73, 118.79, 119.52, 120.39, 121.44, 145.40, 149.50, 205.08; Anal. calcd for C8H8O3: C, 63.15; H, 5.30. Found: C, 63.10; H, 5.33.
4% at 20 - 100℃; for 1 h; Inert atmosphere To a stirred solution of pyrocatechol 1 (70 g, 636.36 mmol) in HOAc (45.8 mL, 763.64 mmol) at RT under an inert atmosphere, was added SnC14 (30 mL, 254.54 mmol). The mixture was heated to 100 °C for 1 h. The mixture was diluted with water (1 L) and CH2C12 (500 mL), stirred for 30 mm, then filtered through a pad of celite eluting with CH2C12 (500 mL). The organic layer was separated, dried (Na2SO4), filtered and concentrated. The crude was purified (silica gel; eluting 10percent EtOAc/hexanes) to afford compound 2 (3.5 g, 4percent) as a pale green solid.‘H NIVIR (500IVIHz, DMSO-d6): 12.00 (br s, 1H), 9.38 (br s, 1H), 7.35 (m, 1H), 7.05 (m, 1H), 6.77 (m, 1H), 2.62 (s, 3H); LC-MS (ESI): m/z 150.9 (M - Hf).
Reference: [1] Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 2, p. 284 - 287
[2] Patent: US2012/15908, 2012, A1, . Location in patent: Page/Page column 16-17
[3] Patent: WO2017/15221, 2017, A1, . Location in patent: Paragraph 00387
  • 3
  • [ 703-98-0 ]
  • [ 13494-10-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 5, p. 547 - 554
  • 4
  • [ 6848-73-3 ]
  • [ 13494-10-5 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 29, p. 10371 - 10387
[2] Chemische Berichte, 1913, vol. 46, p. 4019
  • 5
  • [ 635-67-6 ]
  • [ 13494-10-5 ]
Reference: [1] Journal of Fluorine Chemistry, 2014, vol. 160, p. 77 - 81
  • 6
  • [ 86-51-1 ]
  • [ 13494-10-5 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 29, p. 10371 - 10387
  • 7
  • [ 5653-62-3 ]
  • [ 13494-10-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 5, p. 547 - 554
  • 8
  • [ 2848-25-1 ]
  • [ 13494-10-5 ]
Reference: [1] Australian Journal of Chemistry, 1985, vol. 38, # 4, p. 605 - 614
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