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[ CAS No. 15450-76-7 ] {[proInfo.proName]}

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Chemical Structure| 15450-76-7
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Product Details of [ 15450-76-7 ]

CAS No. :15450-76-7 MDL No. :MFCD00216696
Formula : C9H7NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZXZKYYHTWHJHFT-UHFFFAOYSA-N
M.W : 161.16 Pubchem ID :97250
Synonyms :
Chemical Name :2,8-Dihydroxyquinoline

Calculated chemistry of [ 15450-76-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.59
TPSA : 53.09 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) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : 0.98
Log Po/w (WLOGP) : 1.23
Log Po/w (MLOGP) : 1.04
Log Po/w (SILICOS-IT) : 2.1
Consensus Log Po/w : 1.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.07
Solubility : 1.36 mg/ml ; 0.00845 mol/l
Class : Soluble
Log S (Ali) : -1.68
Solubility : 3.34 mg/ml ; 0.0207 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.153 mg/ml ; 0.000951 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 15450-76-7 ]

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 [ 15450-76-7 ]

* 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 [ 15450-76-7 ]
  • Downstream synthetic route of [ 15450-76-7 ]

[ 15450-76-7 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 15450-72-3 ]
  • [ 15450-76-7 ]
Reference: [1] Canadian Journal of Chemistry, 2005, vol. 83, # 5, p. 460 - 470
  • 2
  • [ 1127-45-3 ]
  • [ 15450-76-7 ]
Reference: [1] Canadian Journal of Chemistry, 2005, vol. 83, # 5, p. 460 - 470
[2] Journal of Fluorescence, 2018, vol. 28, # 5, p. 1121 - 1126
  • 3
  • [ 148-24-3 ]
  • [ 15450-76-7 ]
Reference: [1] Monatshefte fuer Chemie, 1895, vol. 16, p. 761
[2] Chemistry and Industry (London, United Kingdom), 1957, p. 1271
  • 4
  • [ 84-88-8 ]
  • [ 15450-76-7 ]
Reference: [1] Yakugaku Zasshi, 1951, vol. 71, p. 784[2] Chem.Abstr., 1952, p. 4007
[3] Yakugaku Zasshi, 1958, vol. 78, p. 697,698[4] Chem.Abstr., 1958, p. 18406
  • 5
  • [ 15450-76-7 ]
  • [ 31568-91-9 ]
YieldReaction ConditionsOperation in experiment
77% at 20 - 50℃; for 5.5 h; Cooling with ice Synthesis of 50
To a N,N-dimethylformamide (20 ml) suspension of 1 (2.00 g, 12.4 mmol), thionyl chloride (3.56 ml, 49.6 mmol) was added dropwise under ice cooling and stirring, and the mixture was stirred at room temperature for 2 hours, and then thionyl chloride (3.56 ml, 49.6 mmol) was added, followed by further stirring at 50°C for 3.5 hours. The reaction solution was allowed to return to room temperature, poured into ice water and extracted with ethyl acetate. The extraction liquid was washed with water and dried, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n-hexane = 1/20) to obtain 50 (1.72 g, 77percent) as a pale yellow solid. mp 79-80°C, APCI-MS m/z 180/182[M+H]+
Reference: [1] Patent: EP2634177, 2013, A1, . Location in patent: Paragraph 0217; 0218
[2] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 790 - 799
[3] Canadian Journal of Chemistry, 2005, vol. 83, # 5, p. 460 - 470
[4] Patent: WO2004/35549, 2004, A1, . Location in patent: Page 71
[5] Patent: WO2014/100730, 2014, A1, . Location in patent: Paragraph 00314
[6] Journal of Fluorescence, 2018, vol. 28, # 5, p. 1121 - 1126
  • 6
  • [ 15450-76-7 ]
  • [ 139399-61-4 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 790 - 799
[2] Patent: CN108947898, 2018, A,
  • 7
  • [ 15450-76-7 ]
  • [ 93609-84-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 1984, vol. 19, # 4, p. 341 - 346
  • 8
  • [ 15450-76-7 ]
  • [ 343788-51-2 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 1, p. 78 - 83
[2] Patent: WO2014/100730, 2014, A1,
[3] Patent: WO2008/124323, 2008, A1,
[4] Patent: WO2008/121687, 2008, A2,
  • 9
  • [ 15450-76-7 ]
  • [ 343788-51-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5576 - 5585
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