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[ CAS No. 578-67-6 ] {[proInfo.proName]}

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Chemical Structure| 578-67-6
Chemical Structure| 578-67-6
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Product Details of [ 578-67-6 ]

CAS No. :578-67-6 MDL No. :MFCD00006792
Formula : C9H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :GYESAYHWISMZOK-UHFFFAOYSA-N
M.W : 145.16 Pubchem ID :135441757
Synonyms :
Quinolin-5(1H)-one

Calculated chemistry of [ 578-67-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.77
TPSA : 33.12 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) : -5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.39
Log Po/w (XLOGP3) : 1.85
Log Po/w (WLOGP) : 1.94
Log Po/w (MLOGP) : 1.19
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 1.68

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.58
Solubility : 0.383 mg/ml ; 0.00264 mol/l
Class : Soluble
Log S (Ali) : -2.17
Solubility : 0.989 mg/ml ; 0.00682 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.1
Solubility : 0.115 mg/ml ; 0.000791 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.12

Safety of [ 578-67-6 ]

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 [ 578-67-6 ]

* 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 [ 578-67-6 ]
  • Downstream synthetic route of [ 578-67-6 ]

[ 578-67-6 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 333383-80-5 ]
  • [ 580-20-1 ]
  • [ 578-67-6 ]
Reference: [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
  • 2
  • [ 611-34-7 ]
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YieldReaction ConditionsOperation in experiment
64%
Stage #1: With sodium hydrogen sulfate In water for 36 h; Reflux
Stage #2: for 8 h; Reflux
5-(2,2,2-Trifluoroethoxy)quinoline (I-E)
To a stirred solution of amine 5-aminoquinoline (5.0 g, 34.67 mmol) in H2O (100 mL) was added sodium bisulfate (NaHSO3; 25.2 g, 242.1 mmol) at RT, and the mixture was stirred at reflux temperature for 36 h.
The resulting solution was cooled to RT, NaOH (9.7 g, 242.5 mmol) was added, and the mixture was stirred at reflux temperature for 8 h.
After completion of the reaction (monitored by TLC), the reaction mixture was cooled to RT and the pH was adjusted to 7.0 with 6 Normal (N) hydrochloride acid (HCl).
The precipitate was filtered, washed with H2O, and dried under high vacuum to obtain the desired alcohol M (3.2 g, 22.04 mmol, 64percent) as pale-yellow solid. 1H NMR (500 MHz, CDCl3): δ 8.92 (s, 1H), 8.58 (d, J=8.5 Hz, 1H), 7.71 (d, J=8.5 Hz, 1H), 7.53 (t, J=8.0 Hz, 1H), 7.41 (dd, J=8.5, 4.5 Hz, 1H), 6.88 (d, J=7.5 Hz, 1H), 6.10 (br s, 1H). MS (ESI): m/z 146 [M+H]+.
56% With sulfuric acid; acetic acid; sodium nitrite In water at 0℃; for 5.5 h; Inert atmosphere; Reflux 5-aminoquinoline (15.0 g, 104.0 mmol) was dissolved in a solvent of acetic acid / water / sulfuric acid (8: 1: 1, v / v / v, 130 mL) under an argon atmosphere, and a solution of sodium nitrite (8.6 g, 124.8 mmol) dissolved therein. After the reaction mixture was stirred at 0 °C for 30 minutes, 10percent sulfuric acid solution (780 mL) was boiled, slowly added to the reaction solution, The mixture was refluxed for 5 hours, The completion of the reaction was confirmed by TLC (hexane: ethyl acetate = 2: 1). The reaction mixture was cooled to room temperature, and a saturated solution of sodium hydrogencarbonate (250 mL) was added thereto, followed by extraction with ethyl acetate (10 X 400 mL). The organic solvent layer was washed with a saturated solution of sodium chloride (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The concentrate was separated and purified by column chromatography (hexane: ethyl acetate = 2: 1) to obtain the desired compound (8.5 g, 56percent yield).
Reference: [1] Patent: US2012/329802, 2012, A1, . Location in patent: Page/Page column 25-26
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3307 - 3312
[3] Patent: KR101778938, 2017, B1, . Location in patent: Paragraph 0147-0148; 0155; 0160-0162
[4] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 47, p. 431
[5] Journal of the American Chemical Society, 1946, vol. 68, p. 1562
[6] Monatshefte fuer Chemie, 1884, vol. 5, p. 532
[7] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 47, p. 431
  • 3
  • [ 4964-71-0 ]
  • [ 578-67-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4478 - 4482[2] Angew. Chem., 2017, vol. 129, # 16, p. 4549 - 4553,5
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 7, p. 1968 - 1972[4] Angew. Chem., 2018, vol. 130, p. 1986 - 1990,5
[5] Organic Letters, 2017, vol. 19, # 11, p. 3033 - 3036
  • 4
  • [ 177734-78-0 ]
  • [ 578-67-6 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 33, p. 6317 - 6320
  • 5
  • [ 607-34-1 ]
  • [ 578-67-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3307 - 3312
[2] Chemical Biology and Drug Design, 2017, vol. 89, # 1, p. 98 - 113
[3] Patent: KR101778938, 2017, B1,
  • 6
  • [ 1236162-22-3 ]
  • [ 578-67-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 30, p. 3876 - 3878
  • 7
  • [ 333383-80-5 ]
  • [ 580-20-1 ]
  • [ 578-67-6 ]
Reference: [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
  • 8
  • [ 87707-14-0 ]
  • [ 580-16-5 ]
  • [ 578-67-6 ]
  • [ 84244-15-5 ]
Reference: [1] Journal of the American Chemical Society, 1989, vol. 111, # 7, p. 2688 - 2691
[2] Journal of the American Chemical Society, 1989, vol. 111, # 7, p. 2688 - 2691
  • 9
  • [ 87707-14-0 ]
  • [ 580-16-5 ]
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Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 36, p. 4253 - 4256
[2] Tetrahedron Letters, 1986, vol. 27, # 36, p. 4253 - 4256
  • 10
  • [ 3743-29-1 ]
  • [ 578-67-6 ]
Reference: [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
  • 11
  • [ 591-27-5 ]
  • [ 578-67-6 ]
Reference: [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
  • 12
  • [ 81336-58-5 ]
  • [ 578-67-6 ]
  • [ 65-85-0 ]
Reference: [1] Tetrahedron Letters, 1981, vol. 22, # 47, p. 4733 - 4736
  • 13
  • [ 91-22-5 ]
  • [ 148-24-3 ]
  • [ 578-67-6 ]
  • [ 10470-83-4 ]
  • [ 59-31-4 ]
  • [ 529-37-3 ]
  • [ 529-23-7 ]
Reference: [1] Journal of Physical Chemistry B, 1997, vol. 101, # 14, p. 2650 - 2658
  • 14
  • [ 23261-58-7 ]
  • [ 578-67-6 ]
Reference: [1] Chemische Berichte, 1883, vol. 16, p. 721
[2] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 47, p. 431
[3] Dissertation <Muenchen 1883>, S. 18,
  • 15
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  • [ 635-27-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 4, p. 1343 - 1361
[2] Patent: WO2017/31255, 2017, A1, . Location in patent: Paragraph 0074; 0075
  • 16
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  • [ 10470-83-4 ]
YieldReaction ConditionsOperation in experiment
82% With [bis(acetoxy)iodo]benzene In water; acetonitrile at 0℃; for 1 h; Inert atmosphere A solution of iodobenzene diacetate (10.35mmol, 3.3g) in 12mL CH3CN: H2O (2:1) was added to quinolin-5-ol (3) (3.45mmol, 0.50g) at 0°C under N2 and stirred for 1h. After the reaction was completed, water (40mL) was added, and the solution was extracted with EtOAc (3×20mL). The organic phase was washed by brine and concentrated in vacuo to give 4 as a yellow solid, yield 82percent. MS (ESI) m/z = 160 [M+H]+.
Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 34, p. 4871 - 4872
[2] Organic and Biomolecular Chemistry, 2011, vol. 9, # 13, p. 4959 - 4976
[3] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 199 - 209
[4] Synthetic Communications, 1999, vol. 29, # 18, p. 3063 - 3066
  • 17
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  • [ 10470-83-4 ]
Reference: [1] Patent: US4692449, 1987, A,
  • 18
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  • [ 578-67-6 ]
  • [ 10470-83-4 ]
  • [ 59-31-4 ]
  • [ 529-37-3 ]
  • [ 529-23-7 ]
Reference: [1] Journal of Physical Chemistry B, 1997, vol. 101, # 14, p. 2650 - 2658
  • 19
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  • [ 74-88-4 ]
  • [ 6931-19-7 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 0.5 h; Inert atmosphere
4.2
5-Methoxyquinoline (1)
A solution of 5-hydroxyquinoline (4.0 g, 27.6 mmol) in anhydrous DMF (60 mL) was cooled and then added slowly to NaH (1.33 g, 33.12 mmol, 60percent dispersion in mineral oil) at 0 °C under argon atmosphere.
The resulting mixture was stirred at the same temperature for 30 min.
Methyl iodide (4.7 g, 33.12 mmol) was added dropwise to the suspension and the reaction mixture was allowed to warm to room temperature (rt) while stirring for additional 30 min.
The reaction mixture was quenched with water (300 mL) and then extracted with diethyl ether (6 * 100 mL).
The combined organic layers were washed with water and then brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure to afford the title product as brown oil; yield: 4.03 g (92percent); 1H NMR (400 MHz, CDCl3) δ 8.95 (dd, J = 4.2, 2.0 Hz, 1H), 8.62 (dd, J = 8.4, 1.2 Hz, 1H), 7.74 (d, J = 8.0 Hz, 1H), 7.65 (t, J = 8.4 Hz, 1H), 7.42 (dd, J = 8.4, 4.4 Hz, 1H), 6.90 (d, J = 8.0 Hz, 1H), 4.05 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 155.17, 150.66, 148.70, 130.81, 129.37, 121.58, 120.85, 120.19, 104.22, 55.76.
92%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃; for 0.5 h; Inert atmosphere
5-Hydroxyquinoline (4.0 g, 27.6 mmol) was dissolved in N,N-dimethylformamide (60 mL) under argon atmosphere and sodium hydride (1.3 g, 33.1 mmol) was slowly added at 0 °C. After stirring for 30 minutes, Iodomethane (4.7 g, 33.1 mmol) was slowly added to the reaction solution, stirred at room temperature for 30 minutes, The completion of the reaction was confirmed by TLC (hexane: ethyl acetate = 2: 1). The reaction mixture was poured into water (300 mL) And extracted with diethyl ether (6 X 100 mL). The organic solvent layer was washed with saturated sodium chloride solution (600 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent to give the desired compound (4.0 g, 92percent yield).
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 754 - 768
[2] Patent: KR101778938, 2017, B1, . Location in patent: Paragraph 0147-0148; 0155; 0164-0166
[3] Dissertation <Muenchen 1883>, S. 23,
[4] Chemische Berichte, 1882, vol. 15, p. 1979[5] Chemische Berichte, 1887, vol. 20, p. 731
  • 20
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  • [ 77-78-1 ]
  • [ 6931-19-7 ]
Reference: [1] International Journal of Mass Spectrometry, 2015, vol. 390, p. 124 - 131
  • 21
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  • [ 18107-18-1 ]
  • [ 6931-19-7 ]
YieldReaction ConditionsOperation in experiment
42% at 0 - 20℃; for 26 h; Inert atmosphere To a solution of 5-quinolinol (164 mg, 1.13 mmol) in MeOH (7 mL) cooled to 0 °C was slowly added trimethylsilyldiazomethane (6 mL, 0.5 M in Et2O). The reaction mixture was allowed to warm to room temperature and stirred for 26 h. After addition of water, the reaction mixture was extracted with ethyl acetate (3 x 15 mL). The combined organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude oil was purified by column chromatography on silica gel (EtOAc/CH2Cl2/hexane = 1:2:4) to give 5-methoxyquinoline 2a (76 mg, 42percent)
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1472 - 1476
  • 22
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  • [ 4648-54-8 ]
  • [ 6931-19-7 ]
YieldReaction ConditionsOperation in experiment
42% at 0 - 20℃; for 26 h; Inert atmosphere General procedure: To a solution of 5-quinolinol 5 (164 mg, 1.13 mmol) in MeOH (7 mL) cooled to 0 °C was slowly added trimethylsilyldiazomethane (6 mL, 0.5 M in Et2O). The reaction mixture was allowed to warm to room temperature and stirred for 26 h. After addition of water, the reaction mixture was extracted with ethyl acetate (3 × 15mL). The combined organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude oil was purified by column chromatography on silica gel (EtOAc/CH2Cl2/hexane = 1:2:4) to give 5-methoxyquinoline 6a (76 mg, 42percent) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 4.04 (s, 3H), 6.89 (d, J = 7.5 Hz,1H), 7.41 (q, J = 4.2 Hz, 1H), 7.62-7.74 (m, 2H), 8.61 (dd, J= 8.4, 1.2 Hz, 1H), 8.93 (dd, J = 4.2, 1.8 Hz, 1H).
Reference: [1] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 8, p. 2304 - 2310
  • 23
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  • [ 160893-07-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1472 - 1476
[2] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 8, p. 2304 - 2310
[3] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 754 - 768
[4] Chemical Biology and Drug Design, 2017, vol. 89, # 1, p. 98 - 113
[5] Patent: KR101778938, 2017, B1,
  • 24
  • [ 578-67-6 ]
  • [ 160893-04-9 ]
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 754 - 768
[2] Patent: KR101778938, 2017, B1,
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