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[ CAS No. 5060-82-2 ] {[proInfo.proName]}

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Chemical Structure| 5060-82-2
Chemical Structure| 5060-82-2
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Product Details of [ 5060-82-2 ]

CAS No. :5060-82-2 MDL No. :MFCD00075494
Formula : C11H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :UNFNRIIETORURP-UHFFFAOYSA-N
M.W : 174.20 Pubchem ID :853173
Synonyms :

Calculated chemistry of [ 5060-82-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.09
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.46
TPSA : 29.46 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) : 1.92
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 2.55
Log Po/w (MLOGP) : 2.17
Log Po/w (SILICOS-IT) : 2.48
Consensus Log Po/w : 2.27

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.83
Solubility : 0.259 mg/ml ; 0.00149 mol/l
Class : Soluble
Log S (Ali) : -2.48
Solubility : 0.572 mg/ml ; 0.00328 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.62
Solubility : 0.0416 mg/ml ; 0.000239 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 5060-82-2 ]

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 [ 5060-82-2 ]

* 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 [ 5060-82-2 ]
  • Downstream synthetic route of [ 5060-82-2 ]

[ 5060-82-2 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 582-17-2 ]
  • [ 77-78-1 ]
  • [ 3469-26-9 ]
  • [ 5060-82-2 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3272
[2] Tetrahedron, 1982, vol. 38, # 15, p. 2347 - 2354
  • 2
  • [ 67-56-1 ]
  • [ 582-17-2 ]
  • [ 3469-26-9 ]
  • [ 5060-82-2 ]
Reference: [1] Australian Journal of Chemistry, 1993, vol. 46, # 5, p. 731 - 737
  • 3
  • [ 582-17-2 ]
  • [ 77-78-1 ]
  • [ 5060-82-2 ]
YieldReaction ConditionsOperation in experiment
63.4% With potassium carbonate In acetonitrile for 1 h; Reflux General procedure: A mixture of 2-hydroxy-1-nitronaphthalene (500 mg,2.64 mmol), dimethyl sulfate (0.5 ml, 5.3 mmol), and K2CO3 (73.1 mg, 5.3 mmol) inacetonitrile (10 ml) was refluxed for 1hrs. The solvent was evaporated and the residue waspoured into water and extracted with ethyl acetate. The organic layer was washed with waterand brine and dried over anhydrous MgSO4 and concentrated in vacuo. The residue waspurified by column chromatography on silica gel with nhexane/ethyl acetate (15:1) as theeluent to obtain the product
30% With sodium hydroxide In dichloromethane; water at 20℃; for 2 h; Step A: Sodium hydroxide (20 ml, 1M) and dimethyl sulfate (15.0 ml, 158 mmol) were added dropwise to a solution of 2,7-dihydroxynaphthalene (6.6 g, 40 mmol) in dichloromethane (100 ml) and water (60 ml). Additional sodium hydroxide (20 ml, 1M) and dimethyl sulfate (15.0 ml, 158 mmol) were added and the resulting mixture was stirred at room temperature for 2 hours. The two phases were separated and the aqueous layer was extracted with dichloromethane twice. The combined organic extracts were washed with 1 M HCl, dried over magnesium sulfate and concentrated under vacuum. The crude material was purified by column chromatography (5:1 heptane/ethyl acetate) to give 2-hydroxy-7-methoxynaphthalene (2.1 g, 30percent, 100percent AUC HPLC): 1H NMR (300 MHz, CDCl3) δ 7.66-7.70 (m, 2H), 6.94-7.08 (m, 4H), 4.90 (s, 1H), 3.92 (s, 3H).
Reference: [1] Molecular Pharmacology, 2013, vol. 84, # 5, p. 726 - 735
[2] Patent: US2006/52378, 2006, A1, . Location in patent: Page/Page column 112
[3] Journal fuer Praktische Chemie (Leipzig), 1916, vol. <2> 94, p. 25
[4] Journal of medicinal chemistry, 1971, vol. 14, # 11, p. 1023 - 1026
  • 4
  • [ 582-17-2 ]
  • [ 74-88-4 ]
  • [ 5060-82-2 ]
YieldReaction ConditionsOperation in experiment
37% With potassium carbonate In acetone at 0 - 20℃; [0709] To a mixture of naphthalene-2,7-diol (25 g, 156.08 mmol) and K2CO3 (32.3 g, 232.02 mmol) in acetone (300 ml) was added iodomethane (22.2 g, 156.41 mmol) dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature. The solids were filtered off and the filtrate was concentrated under vacuum to give a residue, which was purified by silica gel column chromatography using 1percent-10percent ethyl acetate in petroleum ether to afford 7-methoxynaphthalen-2-ol as a light yellow solid (10 g, 37percent). (ES, m/z): [M+H]+ 175.1; 1H NMR (400 MHz, DMSO-d6): δ 9.65 (s, 1H), 7.65 (d, J=8.8 Hz, 2H), 6.79 (dd, J=13.6, 1.6 Hz, 2H), 6.92-6.89 (m, 2H), 3.84 (s, 3H).
Reference: [1] Patent: US2014/142114, 2014, A1, . Location in patent: Paragraph 0708; 0709
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 25, p. 4665 - 4675
[3] Journal of Organic Chemistry, 1981, vol. 46, p. 4988 - 4991
  • 5
  • [ 1018073-52-3 ]
  • [ 5060-82-2 ]
Reference: [1] Patent: EP2098509, 2009, A1, . Location in patent: Page/Page column 70
  • 6
  • [ 104945-00-8 ]
  • [ 58933-29-2 ]
  • [ 5060-82-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 11, p. 2258 - 2259[2] Zhurnal Organicheskoi Khimii, 1985, vol. 21, # 11, p. 2468 - 2469
  • 7
  • [ 1614-84-2 ]
  • [ 5060-82-2 ]
Reference: [1] Tetrahedron, 1994, vol. 50, # 5, p. 1327 - 1340
  • 8
  • [ 4133-34-0 ]
  • [ 5060-82-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 5, p. 731 - 736
  • 9
  • [ 582-17-2 ]
  • [ 77-78-1 ]
  • [ 3469-26-9 ]
  • [ 5060-82-2 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3272
[2] Tetrahedron, 1982, vol. 38, # 15, p. 2347 - 2354
  • 10
  • [ 67-56-1 ]
  • [ 582-17-2 ]
  • [ 3469-26-9 ]
  • [ 5060-82-2 ]
Reference: [1] Australian Journal of Chemistry, 1993, vol. 46, # 5, p. 731 - 737
  • 11
  • [ 58933-28-1 ]
  • [ 5060-82-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1976, vol. 24, # 2, p. 220 - 223
  • 12
  • [ 5060-82-2 ]
  • [ 4003-89-8 ]
Reference: [1] Chemische Berichte, 1924, vol. 57, p. 1738
  • 13
  • [ 5060-82-2 ]
  • [ 116230-30-9 ]
YieldReaction ConditionsOperation in experiment
19%
Stage #1: With bromine; triphenylphosphine In acetonitrile for 2 h; Reflux
Stage #2: at 250℃; Sealed tube
  Triphenylphosphine (500 mg, 2.9 mmol) was dissolved in   MeCN (5 mL), and   bromine (0.15 mL, 2.9 mmol) was added at 0 °C whilst stirring. The solution was allowed to warm up to rt, and   7-methoxy-naphthalen-2-ol, 44 (490 mg, 2.8 mmol) was added portionwise. The solution was refluxed for 2 h, and the solvent removed in vacuo. The residue was heated to 250 °C in a sealed tube overnight. After cooling to rt, the residue was purified by chromatography using a stepped gradient of 10–20percent   EtOAc in   heptane to yield   45 as a beige solid. Yield: 120 mg (19percent). 1H NMR (CDCl3), δ: 5.17 (br, 1H, OH), 7.06 (d, J = 2.5, 1H, ArH), 7.11 (dd, J = 8.7, 2.4, 1H, ArH), 7.40 (dd, J = 8.7, 2.0, 1H, ArH), 7.63 (d, J = 8.9, 1H, ArH), 7.72 (d, J = 8.9, 1H, ArH), 7.84 (s, 1H, ArH). LC–MS: Rf = 2.01 min; m/z 221/223 ([M+H]+, 100).
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1284 - 1304
  • 14
  • [ 5060-82-2 ]
  • [ 130200-58-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 22, p. 7434 - 7445
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 10, p. 3586 - 3604
[3] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 3, p. 561 - 566
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