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[ CAS No. 108166-01-4 ] {[proInfo.proName]}

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Chemical Structure| 108166-01-4
Chemical Structure| 108166-01-4
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Product Details of [ 108166-01-4 ]

CAS No. :108166-01-4 MDL No. :MFCD02690144
Formula : C12H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KGSIXOOGGCSYTB-UHFFFAOYSA-N
M.W : 201.22 Pubchem ID :2308822
Synonyms :

Calculated chemistry of [ 108166-01-4 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.99
TPSA : 39.19 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) : -5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.42
Log Po/w (XLOGP3) : 2.44
Log Po/w (WLOGP) : 2.33
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 2.78
Consensus Log Po/w : 2.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.99
Solubility : 0.208 mg/ml ; 0.00103 mol/l
Class : Soluble
Log S (Ali) : -2.91
Solubility : 0.25 mg/ml ; 0.00124 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.17
Solubility : 0.0136 mg/ml ; 0.0000678 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 108166-01-4 ]

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

Application In Synthesis of [ 108166-01-4 ]

* 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 [ 108166-01-4 ]
  • Downstream synthetic route of [ 108166-01-4 ]

[ 108166-01-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 67-56-1 ]
  • [ 635-80-3 ]
  • [ 108166-01-4 ]
YieldReaction ConditionsOperation in experiment
59% at 0 - 65℃; for 12 h; Step 2: methyl 2-methylquinoline-6-carboxylate: To a solution of 2-methylquinoline-6- carboxylic acid (3.0 g, 16.20 mmol) in methanol (30 ml.), sulphuric acid ( 3ml) was added dropwise at 0°C and then stirred at 65°C for 12h. The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (1.9 g, 59percent).
59% at 0 - 65℃; for 12 h; Step 2:
methyl 2-methylquinoline-6-carboxylate
To a solution of 2-methylquinoline-6-carboxylic acid (3.0 g, 16.20 mmol) in methanol (30 ml.), sulphuric acid (3 ml) was added dropwise at 0° C. and then stirred at 65° C. for 12 h.
The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added.
The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (1.9 g, 59percent).
Reference: [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 929 - 931
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12224 - 12227[3] Angew. Chem., 2016, vol. 128, # 40, p. 12412 - 12415,4
[4] Patent: WO2013/144737, 2013, A2, . Location in patent: Paragraph 252
[5] Patent: US2015/57309, 2015, A1, . Location in patent: Paragraph 0525
[6] Patent: WO2015/49535, 2015, A1, . Location in patent: Paragraph 00321
  • 2
  • [ 598-32-3 ]
  • [ 17012-22-5 ]
  • [ 108166-01-4 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 10, p. 2494 - 2497
  • 3
  • [ 109-92-2 ]
  • [ 619-45-4 ]
  • [ 108166-01-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 33, p. 7670 - 7673
  • 4
  • [ 19718-49-1 ]
  • [ 108166-01-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 30, p. 6349 - 6352
  • 5
  • [ 150-13-0 ]
  • [ 108166-01-4 ]
Reference: [1] Patent: WO2013/144737, 2013, A2,
[2] Patent: US2015/57309, 2015, A1,
  • 6
  • [ 635-80-3 ]
  • [ 108166-01-4 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1987, vol. 57, p. 96 - 99[2] Zhurnal Obshchei Khimii, 1987, vol. 57, # 1, p. 113 - 117
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