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[ CAS No. 372941-54-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 372941-54-3
Chemical Structure| 372941-54-3
Structure of 372941-54-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 372941-54-3 ]

CAS No. :372941-54-3 MDL No. :MFCD18252485
Formula : C20H19FN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ASGSMDPSNUXWMB-UHFFFAOYSA-N
M.W : 338.38 Pubchem ID :11484526
Synonyms :

Calculated chemistry of [ 372941-54-3 ]

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.3
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 91.74
TPSA : 53.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.17
Log Po/w (XLOGP3) : 3.44
Log Po/w (WLOGP) : 3.76
Log Po/w (MLOGP) : 3.04
Log Po/w (SILICOS-IT) : 4.48
Consensus Log Po/w : 3.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.13
Solubility : 0.0251 mg/ml ; 0.0000741 mol/l
Class : Moderately soluble
Log S (Ali) : -4.24
Solubility : 0.0194 mg/ml ; 0.0000574 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.74
Solubility : 0.0000613 mg/ml ; 0.000000181 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.46

Safety of [ 372941-54-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 372941-54-3 ]

* 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.

  • Downstream synthetic route of [ 372941-54-3 ]

[ 372941-54-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 372941-54-3 ]
  • [ 125803-03-4 ]
YieldReaction ConditionsOperation in experiment
84% With ammonium hydroxide; sulfuric acid In tetrahydrofuran; toluene 1 5-Aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran Example 1 5-Aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran 1-(3-Dimethylamino-propyl)-1-(4-fluoro-phenyl)-3-oxo-1,3-dihydro-isobenzofuran-5-carbonitrile (5.4 g, 16.2 mmol) was dissolved in dry THF (5 mL) and diluted with dry ether (50 mL). This solution was added dropwise to a refluxing suspension of lithium aluminium hydride (2.5 g, 65 mmol) in dry ether (150 mL) over 10-15 minutes, after which the resulting suspension was heated at reflux for a further 4 h. The solution was allowed to cool to room temperature and was stirred at room temperature overnight. The reaction was quenched with a minimum of water, and the resulting solution/suspension was dried over anhydrous magnesium sulfate. The mixture was filtered, and the solid cake was washed with THF. The combined filtrates were evaporated to give an oil. The oil was dissolved in toluene (200 mL) and was stirred with an aqueous solution of sulfuric acid (10 ml, 70% v/v) for 3 h. The mixture was diluted with water, and the pH was adjusted to >9 by the addition of aqueous ammonia solution (25% w/v). The toluene was separated, and the aqueous phase was extracted with further toluene. The combined toluene extracts were dried over anhydrous magnesium sulfate, filtered and evaporated to give the title compound as a yellow oil (4.4 g, 84%). 1H NMR (CDCl3): δ 1.25-1.40 (m, 1H), 1.40-1.55 (m, 1H), 2.11 (ddd, 1H), 2.13 (t, 3H), 2.15 (ddd, 1H), 2.21 (t, 2H), 3.85 (s, 2H), 5.11 (d, 1H), 5.14 (d, 1H), 6.96 (t, 2H), 7.15 (s, 1H), 7.21 (d, 1H), 7.22 (d, 1H), 7.45 (dd, 2H).
  • 2
  • [ 103146-25-4 ]
  • [ 372941-54-3 ]
YieldReaction ConditionsOperation in experiment
71.5% With Jones reagent; sodium hydroxide In acetone at -5℃; At 80°C, 7g 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-hydroxybutyl]-3-hydroxymethyl benzonitrile hydrobromide The acid salt was dissolved in purified water, adjusted to pH 11 with 40% NaOH, washed with dichloromethane and saturated brine for extraction, collected the organic phase, dried over anhydrous sodium sulfate, filtered with suction, and the filtrate was rotary evaporated to obtain 5.4g of free 4- [4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-hydroxybutyl]-3-hydroxymethylbenzonitrile. At room temperature, dissolve 5g of free 4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-hydroxybutyl]-3-hydroxymethyl benzonitrile Add Jones reagent (2.7g CrO3 dissolved in 8.3mL H2SO4/H2O) in 50mL of acetone, drop the temperature to -5°C, slowly dropwise add Jones reagent (2.7g CrO3 dissolved in 8.3mL H2SO4/H2O), after the addition is complete, continue to stir, TLC monitors the progress of the reaction (dichloromethane: methanol = 5:1). At -5°C, 100 mL of purified water was added to the reaction solution, and the pH was adjusted to about 11 with 40% NaOH to produce a large amount of inorganic salts. Suction filtration with diatomaceous earth, purified water, washing the filter cake with dichloromethane, extracting the filtrate with dichloromethane 3 times, washing the organic phase with purified water 2 times, collecting the organic phase, drying with anhydrous sodium sulfate, filtering, and rotary evaporation under reduced pressure From the filtrate, 3.6 g of impurity C oil was obtained, with a yield of 71.5% and a purity of 96.33% (HPLC area normalization method).
  • 3
  • [ 372941-54-3 ]
  • 3-hydroxycitalopram [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With diisobutylaluminium hydride In tetrahydrofuran at -75 - -65℃; for 0.333333h; Inert atmosphere; In a nitrogen environment, 4g impurity C was put into a 250mL three-necked flask, 40mL anhydrous tetrahydrofuran was added, liquid nitrogen was cooled to -70°C, 40mL DIBAL-H was added dropwise with a syringe, the reaction was kept warm for 20min, and the progress of the reaction was monitored by TLC. After the reaction is completed, slowly warm up to -30°C, add 1.87mL of water, 1.87mL of 15% sodium hydroxide, and then add 4.68mL of water to quench the reaction solution, slowly warm to 15°C, add anhydrous sodium sulfate to dry, filter, and filtrate Distill under reduced pressure, pass through a silica gel column (CH2Cl2:CH3OH=10:1), collect product points, and rotary steam to obtain 1.2 g of oily liquid, yield: 30%, purity: 98.53% (HPLC area normalization method).
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