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[ CAS No. 6964-62-1 ] {[proInfo.proName]}

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Chemical Structure| 6964-62-1
Chemical Structure| 6964-62-1
Structure of 6964-62-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6964-62-1 ]

CAS No. :6964-62-1 MDL No. :
Formula : C23H20N2O Boiling Point : -
Linear Structure Formula :- InChI Key :WEENRMPCSWFMTE-UHFFFAOYSA-N
M.W : 340.42 Pubchem ID :248986
Synonyms :

Calculated chemistry of [ 6964-62-1 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 22
Fraction Csp3 : 0.09
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 107.01
TPSA : 45.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.47
Log Po/w (XLOGP3) : 5.41
Log Po/w (WLOGP) : 4.94
Log Po/w (MLOGP) : 3.63
Log Po/w (SILICOS-IT) : 4.85
Consensus Log Po/w : 4.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.72
Solubility : 0.000647 mg/ml ; 0.0000019 mol/l
Class : Moderately soluble
Log S (Ali) : -6.11
Solubility : 0.000262 mg/ml ; 0.00000077 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.61
Solubility : 0.00000083 mg/ml ; 0.0000000024 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.9

Safety of [ 6964-62-1 ]

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 [ 6964-62-1 ]

* 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 [ 6964-62-1 ]
  • Downstream synthetic route of [ 6964-62-1 ]

[ 6964-62-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 826-81-3 ]
  • [ 100-52-7 ]
  • [ 62-53-3 ]
  • [ 6964-62-1 ]
YieldReaction ConditionsOperation in experiment
54%
Stage #1: at 20℃; for 0.0833333 h;
Stage #2: With pyridine In ethanol at 100℃; for 24 h;
Aniline (0.465 g, 5.0 mmol) and benzaldehyde (0.53 g, 5.0 mmol) were dissolved in ethanol (10 mL) followed by stirring at room temperature for about 5 minutes.
To the mixture, 2-methyl-8-quinolinol (0.795 g, 5.0 mmol) and catalytic pyridine (2 drops) was added and the reaction mixture was refluxed up to 100 °C for about 24 h.
The reaction was monitored by TLC (3:2 acetonitrile/water) and LC-MS. Ethanol was removed by rotary evaporation to afford a crude solid, which was purified by flash chromatography using 2percent ethyl acetate in hexane.
The column fractions containing the compound were kept overnight in the hood to obtain needle shaped crystals (0.92 g, 54percent).
1H NMR (500 MHz, CDCl3, δ): 7.97 (d, J = 8.4 Hz, 1H), 7.51 (d, J = 8.5 Hz, 1H), 7.48 (m, 2H), 7.31 (m, 2H), 7.24 (m, 3H), 7.10 (m, 2H), 6.67 (m, 1H), 6.63 (m, 2H), 6.12 (d, J = 3.4 Hz, 1H), 4.49 (s, 1H), 2.69 (s, 3H); 13C NMR (125 MHz, CDCl3, δ): 157.3, 148.6, 147.7, 142.8, 137.8, 136.2, 129.3, 128.8, 127.6, 127.4, 125.8, 125.7, 124.2, 122.7, 117.86, 117.78, 113.8, 57.0, 25.1; HRMS-ESI (m/z): [M-C6H6N]+ calcd for C23H20N2O 248.10754, found 248.10762. Anal. Calcd for C23H20N2O: C, 81.15; H, 5.92; N, 8.23. Found: C, 80.88; H, 5.89; N, 8.17. HPLC (Method-B) Rt = 2.770 (>95percent).
Reference: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 160 - 178
[2] Journal of Organic Chemistry, 1956, vol. 21, p. 692
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