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[ CAS No. 16712-64-4 ] {[proInfo.proName]}

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Chemical Structure| 16712-64-4
Chemical Structure| 16712-64-4
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Product Details of [ 16712-64-4 ]

CAS No. :16712-64-4 MDL No. :MFCD00060070
Formula : C11H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :KAUQJMHLAFIZDU-UHFFFAOYSA-N
M.W : 188.18 Pubchem ID :85557
Synonyms :

Calculated chemistry of [ 16712-64-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.93
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 : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.29
Log Po/w (XLOGP3) : 1.78
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 2.02
Log Po/w (SILICOS-IT) : 1.84
Consensus Log Po/w : 1.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.59
Solubility : 0.483 mg/ml ; 0.00257 mol/l
Class : Soluble
Log S (Ali) : -2.61
Solubility : 0.466 mg/ml ; 0.00247 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.87
Solubility : 0.252 mg/ml ; 0.00134 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 16712-64-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16712-64-4 ]

* 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 [ 16712-64-4 ]
  • Downstream synthetic route of [ 16712-64-4 ]

[ 16712-64-4 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 64-17-5 ]
  • [ 16712-64-4 ]
  • [ 17295-12-4 ]
YieldReaction ConditionsOperation in experiment
99% at 0 - 20℃; for 72 h; Compound 161a:; 161aTo an ethanol solution (50 mL ) of 6-hydroxy-naphthalene-2-carboxylic acid (5.29 g, 28.0 mmol) was added thionyl chloride (6 mL ) at 0°C. The mixture was stirred at room temperature for 72h. Excess reagents were evaporated. The residue was dissolved in ethyl acetate (100 mL ). The ethyl acetate solution was washed with water (80 ml_), cold 1 M sodium bicarbonate (80 ml.) and brine (80 mL ). It was dried over Na2SO4 and concentrated to give the crude title compound in 99percent yield. 1H NMR (CDCI3): δ 8.53 (1 H, br s), 8.01 (1 H, dd, J=8.5, 1.7Hz), 7.86 (1 H, d, J=8.5Hz), 7.20-7.13 (2H, m), 4.43 (2H, q, J=7.3Hz), 1.43 (3H, t, J=7.1 Hz). LCMS (APCl): 217.1 (M+H+).
85% for 2 h; Reflux To the solution of 6-hydroxy-2-naphthaoic acid (10.0 g, 0.053 mol) dissolved in 100 mL of EtOH was added 2.0 mL of H2SO4, and this solution was refluxed for 2 h. The solution was cooled and neutralized with 0.5 M of aqueous NaOH. The solids were collected. The product isolated as white solids were obtained after recrystallization from ethanol. Yield 85percent. 1H NMR (300 MHz, CDCl3): δ 3.95 (s, 3H, -OCH3), 5.74 (s, 1H, Ar-OH), 7.15 (d, 2H, Ar-H, J=7.6 Hz), 7.67 (d, 1H, Ar-H, J=8.6 Hz), 7.83 (d, 1H, Ar-H, J=9.7 Hz), 7.98 (d, 1H, Ar-H, J=8.7 Hz), 8.51 (s, 1H, Ar-H). 13C NMR (75 MHz, CDCl3): δ 50.00, 109.31, 118.52, 125.31, 125.91, 126.53, 127.94, 130.72, 131.24, 136.43, 155.65, 167.00.
Reference: [1] Patent: WO2006/40646, 2006, A1, . Location in patent: Page/Page column 97
[2] Journal of Physical Chemistry A, 2016, vol. 120, # 33, p. 6563 - 6574
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 14, p. 3518 - 3536
[4] Molecular Crystals and Liquid Crystals, 2008, vol. 494, p. 282 - 292
[5] Tetrahedron, 2013, vol. 69, # 43, p. 9045 - 9055
[6] Journal of the American Chemical Society, 1950, vol. 72, p. 2112,2114
[7] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 13, p. 4279 - 4290
[8] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2019, vol. 210, p. 266 - 274
  • 2
  • [ 16712-64-4 ]
  • [ 17295-12-4 ]
Reference: [1] Patent: US2003/144329, 2003, A1,
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2465 - 2481
  • 3
  • [ 67-56-1 ]
  • [ 16712-64-4 ]
  • [ 77-76-9 ]
  • [ 17295-11-3 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride In water at 20 - 55℃; for 32 h; Example 1; Preparation of 6-{ l-[4-(3,3-dimethyl-2-oxobutoxy)-3-methylphenyl]-l- ethylpropyl }naphthalene-2-carboxylic acid; A. 6-Hydroxynaphthalene-2-carboxylic acid methyl ester; Treat a mixture of 6-hydroxy-2-naphthoic acid (4.45g, 23.6 mmol) in 2,2- dimethoxypropane (235 mL) with cone. HCl (24 mL) and then MeOH (60 mL). Stir tlie reaction at RT for 16 h and then at 55 0C for 16 h. Pour the reaction mixture into EtOAc (250 mL) and wash with brine (3 x 100 mL). Dry the organic layer over Na2SO4, concentrate the filtrate, and chromatograph the concentrated filtrate (0.5 kg silica gel, 5:95 to 15:85 EtOAc:hex) to give the title compound (4.77 g, quant). MS (ES) m/e 203 (M+l).
Reference: [1] Patent: WO2006/69153, 2006, A2, . Location in patent: Page/Page column 25
  • 4
  • [ 67-56-1 ]
  • [ 16712-64-4 ]
  • [ 17295-11-3 ]
YieldReaction ConditionsOperation in experiment
90% for 24 h; Reflux The solution of 6-hydroxy-2-naphthaoic acid (10.0g, 0.053mol) dissolved in CH3OH was slowly added 2.0mL of concentrated H2SO4 and the solution was refluxed for 24h. The solution was cooled to room temperature, and the solids as light brown solids were collected. The solids were purified by recrystallization from methanol. Yield 90percent. 1H NMR (500MHz, CDCl3): δ 3.95 (s, 3H, –OCH3), 5.74 (s, 1H, Ar–OH), 7.15 (d, 2H, Ar–H, J=7.62Hz), 7.67 (d, 1H, Ar–H, J=8.58Hz), 7.83 (d, 1H, Ar–H, J=9.69Hz), 7.98 (d, 1H, Ar–H, J=8.72Hz), 8.51 (s, 1H, Ar–H). 13C NMR (125MHz, CDCl3): δ 50.0, 109.3, 118.5, 125.3, 125.9, 126.5, 127.9, 130.7, 131.2, 136.4, 155.6, 167.0.
84% for 8 h; Heating / reflux A solution of 15.7 g (83.4 mmol) of 6-hydroxy-2-naphthoic acid is refluxed for 8 hours in a mixture of 160 ml of methanol and 8 ml of concentrated sulphuric acid. After cooling, the product precipitates out. After filtration and washing with isopropyl ether, 14.1 g of methyl 6-hydroxynaphthalene-2-carboxylate are obtained in the form of a beige-coloured solid in a yield of 84percent.
80% for 2 h; Reflux The solution of 6-hydroxy-2-naphthaoic acid (10.0 g, 0.053 mol) dissolved in 100 mL of CH3OH was added 2.0 mL of concentrated H2SO4, and the mixture was refluxed for 2 h.The solution was neutralized with dilute aqueous NaOH(aq). The solids were collected, andt he priduct isolated as white solids were obtained after recrystallization from CH3OH. Yield 80percent.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 7, p. 1560 - 1568
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 23, p. 7486 - 7494
[3] ChemMedChem, 2010, vol. 5, # 9, p. 1577 - 1593
[4] Tetrahedron, 2013, vol. 69, # 21, p. 4226 - 4235
[5] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 10, p. 1403 - 1408
[6] Patent: WO2004/52840, 2004, A1, . Location in patent: Page 33
[7] Tetrahedron, 2012, vol. 68, # 36, p. 7331 - 7337
[8] Journal of Medicinal Chemistry, 1997, vol. 40, # 8, p. 1186 - 1194
[9] Organic Letters, 2017, vol. 19, # 7, p. 1808 - 1811
[10] Synthetic Communications, 2012, vol. 42, # 17, p. 2526 - 2539
[11] MedChemComm, 2014, vol. 5, # 8, p. 1247 - 1253
[12] Letters in Drug Design and Discovery, 2011, vol. 8, # 1, p. 26 - 31
[13] Journal of Medicinal Chemistry, 2001, vol. 44, # 18, p. 2869 - 2878
[14] Journal of the American Chemical Society, 2010, vol. 132, # 32, p. 11288 - 11305
[15] Journal of Medicinal Chemistry, 2013, vol. 56, # 3, p. 761 - 780
[16] Journal of Organic Chemistry, 2014, vol. 79, # 15, p. 7132 - 7140
[17] Journal of Medicinal Chemistry, 2015, vol. 58, # 2, p. 560 - 576
[18] Carbohydrate Research, 2017, vol. 446-447, p. 76 - 84
[19] Patent: JP2018/2689, 2018, A, . Location in patent: Paragraph 0075; 0076
  • 5
  • [ 16712-64-4 ]
  • [ 17295-11-3 ]
Reference: [1] Patent: US6087304, 2000, A,
[2] Patent: US5773421, 1998, A,
[3] Patent: US5061399, 1991, A,
  • 6
  • [ 16712-64-4 ]
  • [ 77-78-1 ]
  • [ 17295-11-3 ]
Reference: [1] Patent: WO2003/104178, 2003, A1, . Location in patent: Page 70-71
  • 7
  • [ 7664-93-9 ]
  • [ 16712-64-4 ]
  • [ 17295-11-3 ]
Reference: [1] Patent: US2003/134885, 2003, A1,
  • 8
  • [ 16712-64-4 ]
  • [ 101752-05-0 ]
  • [ 17295-11-3 ]
Reference: [1] Patent: US6069149, 2000, A,
  • 9
  • [ 16712-64-4 ]
  • [ 78119-82-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 666 - 680
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