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[ CAS No. 36263-51-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 36263-51-1
Chemical Structure| 36263-51-1
Chemical Structure| 36263-51-1
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Product Details of [ 36263-51-1 ]

CAS No. :36263-51-1 MDL No. :MFCD00021282
Formula : C14H17NO Boiling Point : -
Linear Structure Formula :- InChI Key :YQXUSXSQFVWPRQ-UHFFFAOYSA-N
M.W : 215.29 Pubchem ID :98629
Synonyms :

Calculated chemistry of [ 36263-51-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 64.26
TPSA : 33.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.57
Log Po/w (XLOGP3) : 3.52
Log Po/w (WLOGP) : 3.42
Log Po/w (MLOGP) : 2.46
Log Po/w (SILICOS-IT) : 3.6
Consensus Log Po/w : 3.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.54
Solubility : 0.0624 mg/ml ; 0.00029 mol/l
Class : Soluble
Log S (Ali) : -3.9
Solubility : 0.0273 mg/ml ; 0.000127 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.27
Solubility : 0.0115 mg/ml ; 0.0000532 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.59

Safety of [ 36263-51-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 36263-51-1 ]

* 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.

  • Downstream synthetic route of [ 36263-51-1 ]

[ 36263-51-1 ] Synthesis Path-Downstream   1~28

YieldReaction ConditionsOperation in experiment
p-Methoxyphenylacetonitril, 1,5-Dibrompropan;
4-Methoxy-phenylacetonitril, 1.5-Dibrom-pentan, NaOH;
  • 2
  • [ 104-92-7 ]
  • [ 15057-00-8 ]
  • [ 36263-51-1 ]
YieldReaction ConditionsOperation in experiment
77% With tris(dibenzylideneacetone)dipalladium (0); zinc(II) fluoride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 90℃; for 24h;
  • 3
  • [ 36263-51-1 ]
  • 5-[1-(4-methoxyphenyl)cyclohexyl]-2H-tetrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With trimethylsilylazide; di(n-butyl)tin oxide In 1,4-dioxane at 140℃; for 8h; microwave irradiation;
  • 4
  • [ 104-92-7 ]
  • [ 766-05-2 ]
  • [ 36263-51-1 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: cyclohexane carbonitrile With zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex In tetrahydrofuran at 25℃; Inert atmosphere; Stage #2: 1-bromo-4-methoxy-benzene With palladium diacetate In tetrahydrofuran at 50℃; for 3h; Inert atmosphere;
72% Stage #1: cyclohexane carbonitrile With lithium diisopropyl amide In diethyl ether at 20℃; for 2h; Stage #2: 1-bromo-4-methoxy-benzene With palladium diacetate; tri-tert-butyl phosphine; zinc(II) chloride In tetrahydrofuran at 23℃; for 12h;
  • 5
  • [ 111-24-0 ]
  • [ 104-47-2 ]
  • [ 36263-51-1 ]
YieldReaction ConditionsOperation in experiment
71% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; 2.1 Step 1: Preparation of1 -(4-methoxyphenyl)cyclohexanecarbonitrile Sodium hydride (2.85 g, 71.3 mmol) was dissolved in dimethylformamide (50 mE), to which 2-(4-methoxyphe- nyl)acetonitrile (5.0 g, 33.97 mmol) and 1,5-dibromopen- tane (9.37 g, 40.77 mmol) were loaded at 00 C. The reaction mixture was stirred at room temperature for 2 hours. Water was added thereto to terminate the reaction, followed by extraction twice with ethylacetate. The extracted organic layer was dried over sodium sulfate and then filtered. The solvent was eliminated by distillation under reduced pressure. Then, purification was performed by silica gel column chromatography (eluent: ethylacetate/hexane, 1/1) to give the target compound 1 -(4-methoxyphenyl)cyclohexanecar- bonitrile as a white solid (5.2 g, 24.152 mmol, yield: 7 1%). 1H-NMR (300 MHz, CDC13) ö 7.40 (d, J=9.0 Hz, 2H), 6.91 (d, J=8.7 Hz, 2H), 3.81 (s, 3H), 2.12-2.16 (m, 2H),1.58-1.85 (m, 7H), 1.24-1.28 (m, 1H); LC/MS 216.1 [M+H].
63% With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 1.78333 - 1.8h; 1; 19 To a solution of 4-methoxyphenylacetonitrile (E1) (1.002 g, 6.8 mmol) and 1,5-dibromopentane (1.886 g, 8.2 mmol) in dry dimethylformamide (15 ml) at ice bath temperature slowly (ca. 2-3 minutes) a 60% suspension of NaH in mineral oil (0.579 g, 14.4 mmol) was added. The obtained reaction mixture was stirred for 15 minutes at ice bath temperature and for 1.5 hours at room temperature, then the contents were poured into benzene (75 ml). The mixture was successively washed with water (3 x 75 ml), brine (25 ml), and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silicagel (50 g) with petroleum ether-ethyl acetate (5 : 1) as eluent to give the title compound (0.924 g, 63%) as a white solid. 1H NMR (CDCl3, HMDSO) δ: 1.00-2. 28 (10H, m); 3.81 (3H, s); 6.90 (2H, d, J=9.0 Hz); 7.40 (2H, d, J=9.0 Hz).
With potassium-t-butoxide In dimethyl sulfoxide at 0 - 20℃; for 17h; 11.P1 P1. Weigh 25 g of 4-fluorobenzeneacetonitrile into a three-necked flask, add 125 ml of dimethyl sulfoxide to dissolve, cool the solution to 0°C under ice-water bath conditions, and stir at a rate of 600 r/min until the reaction ends, add 40 g of potassium tert-butoxide, 39 g of 1,5-dibromopentane were added dropwise at a rate of 1 ml/min, the temperature was controlled at 5-10 °C for 2 h, the ice-water bath was removed, the temperature was raised at 20 °C, and the temperature was increased Control the reaction at 20°C for 15h, add 250ml of ice water to quench the reaction after the reaction, extract twice with ethyl acetate, use 130ml of ethyl acetate for each extraction, combine the organic phases after the extraction is complete, use saturated sodium chloride solution (20 °C, saturated solution at standard atmospheric pressure), and the solvent was spun dry by rotary evaporator to give 1-(4-methoxyphenyl)-1-cyclohexanecarbonitrile
  • 6
  • [ 36263-51-1 ]
  • [ 7469-83-2 ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: 1-(4-methoxyphenyl)cyclohexane carbonitrile With sodium hydroxide; dihydrogen peroxide In 1,3-dioxane; water for 96h; Heating / reflux; Stage #2: With hydrogenchloride In 1,3-dioxane; water 2; 21 A solution of 1-(4-methoxyphenyl)cyclohexanecarbonitrile (E2) (1.092 g, 5.07 mmol) in dioxane (6 ml) to a mixture of 2 M NaOH in water (150 ml) and 30% H202 in water (7.5 ml) was added and the resultant suspension was stirred under reflux for 4 days. The pH of the reaction medium was brought to pH 1 with conc. HCl (ca. 30 ml) and the obtained mixture was extracted with ethyl acetate (4 x 80 ml). The combined organic extract was washed with brine (50 ml) and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silicagel (50 g) with benzene-ethyl acetate-acetic acid (9: 1: 0.15) as eluent affording the title compound (0.844 g, 71%) as a white solid. 1H NMR (CDCl3, HMDSO) δ: 1.05-1. 91 (8H, m); 2.16-2. 61 (2H, m); 3.76 (3H, S) ; 6.86 (2H, d, J=9.0 Hz); 7.34 (2H, d, J=9.0 Hz); 11.26 (1 H, br s).
With potassium hydroxide In ethylene glycol for 4h; Reflux; Inert atmosphere;
  • 7
  • [ 36263-51-1 ]
  • [ 868849-59-6 ]
YieldReaction ConditionsOperation in experiment
91% With boron tribromide In dichloromethane at 0 - 20℃; for 48h; 26 Intermediate 26: 1-(4-hydroxyphenyl)cyclohexanecarbonitrile; [] To a solution of 1-(4-methoxyphenyl)cyclohexanecarbonitrile (2 g, 9.29 mmol) in DCM (40 mL) at 0°C under N2 was added dropwise BBr3 (2.63 mL, 27.87 mmol). The reaction was allowed to warm to room temperature and stirred for 48hours. The mixture was stirred for 3 hours at 0°C and quenched with water (30 mL). The mixture was separated and the organic layer was washed with a saturated aqueous solution of NaHCO3 then water. The combined organic extracts were dried over Na2SO4, filtered, concentrated in vacuo and purified by colomn chromatography on silica gel eluting with DCM:acetone (97:3) to give the title compound (1.71 g, 91%).
With boron tribromide In dichloromethane at 20℃; for 25h; 35 l-(4-Methoxyphenyl)-l-cyclohexanexanecarbonitrile (100 mg, 0.46 mmol) was dissolved in dichloromethane (5 mL) and a solution of boron tribromide in dichloromethane (IM; 0.5 mmol, 0.5 mL) was added dropwice. Stirred at room temperature for Ih, concentrated. 1H NMR the reaction had proceeded 20%. The syrup was dissolved in dichloromethane and a solution of boron tribromide in dichloromethane (1 mL, 1.0 mmol) was added. The solution was stirred for 24h, concentrated and worked- up by flash chromatography. Yield: 82 mg. . LC/MS purity (UV/MS): 100/90%, Rt 6.0 min. M- 1 : 200[00268] 1H NMR (400 MHz, CD3Cl): 7.34-7.29 (m, 2H), 6.87-6.83 (m, 2H), 2.16-2.10 (m, 2H), 1.90-1.66 (m, 8H).
  • 8
  • [ 197654-64-1 ]
  • [ 36263-51-1 ]
  • 5-(1-Cyanocyclopentyl)-2-methoxybenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
11.i (i) (i) 5-(1-Cyanocyclopentyl)-2-methoxybenzaldehyde (Compound 51) This compound was prepared from 4-(1-Cyanocyclohexyl)anisole in the same manner of Compound 2. 1 H-NMR (CDCl3) 10.46 (s, 1H), 7.88-7.00 (m, 3H), 3.96 (s, 3H), 2.56-1.86 (s, 10H)
  • 9
  • [ 7677-24-9 ]
  • [ 17138-79-3 ]
  • [ 36263-51-1 ]
YieldReaction ConditionsOperation in experiment
93% With indium(III) bromide In dichloromethane at 20℃; Inert atmosphere;
  • 10
  • [ 7677-24-9 ]
  • [ 20758-60-5 ]
  • [ 36263-51-1 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: trimethylsilyl cyanide With trifluorormethanesulfonic acid In 4-methyl-1,2,3-trifluorobenzene at -20℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-(4-methoxyphenyl)cyclohexene In 4-methyl-1,2,3-trifluorobenzene at -20 - -5℃; Inert atmosphere;
  • 11
  • [ 36263-51-1 ]
  • (+/-) 1-(1-(4-methoxyphenyl)cyclohexyl)ethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene 2: sodium tetrahydroborate / methanol
  • 13
  • [ 36263-51-1 ]
  • [ 1419174-50-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethylene glycol / 4 h / Reflux; Inert atmosphere 2: cesium acetate; palladium diacetate; [bis(acetoxy)iodo]benzene; silver(I) acetate; sodium acetate / chlorobenzene; <i>tert</i>-butyl alcohol / 12 h / 100 °C / Inert atmosphere
  • 14
  • [ 36263-51-1 ]
  • [ 1429442-39-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 22 h / 20 - 75 °C 1.2: 18 h / 75 °C 2.1: titanium (IV) ethoxide / tetrahydrofuran / 8 h / 85 °C
  • 15
  • [ 36263-51-1 ]
  • [ 1429442-40-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 22 h / 20 - 75 °C 1.2: 18 h / 75 °C 2.1: titanium (IV) ethoxide / tetrahydrofuran / 8 h / 85 °C 3.1: lithium diisopropyl amide / toluene / -78 °C
  • 16
  • [ 36263-51-1 ]
  • [ 100-58-3 ]
  • [ 1429442-65-8 ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: 1-(4-methoxyphenyl)cyclohexane carbonitrile; phenylmagnesium bromide In tetrahydrofuran at 20 - 75℃; for 22h; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 75℃; for 18h;
  • 17
  • [ 459-60-9 ]
  • [ 766-05-2 ]
  • [ 36263-51-1 ]
YieldReaction ConditionsOperation in experiment
31% With potassium hexamethylsilazane In tetrahydrofuran at 60℃; for 96h;
  • 18
  • [ 36263-51-1 ]
  • [ 613-36-5 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydride; sodium iodide In tetrahydrofuran; mineral oil at 85℃; for 13h; Inert atmosphere; Sealed tube;
  • 19
  • [ 36263-51-1 ]
  • [ 56140-77-3 ]
  • [ 613-36-5 ]
YieldReaction ConditionsOperation in experiment
1: 42% 2: 37% With sodium hydride; lithium iodide In tetrahydrofuran; mineral oil at 85℃; for 2.5h; Inert atmosphere; Sealed tube;
  • 20
  • [ 36263-51-1 ]
  • N-((1-(3-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidine-2-yl)amino)-4-methoxyphenyl)cyclohexyl)methyl)-2,2,2-trifluoroacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydroxide; lithium aluminium tetrahydride / diethyl ether / 4 h / 0 - 20 °C 1.2: 0.33 h / 0 °C 2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3.1: nitric acid; trifluoroacetic acid / 2 h / 0 °C 4.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h 5.1: hydrogenchloride / 2-ethoxy-ethanol / 15 h / 80 °C
  • 21
  • [ 36263-51-1 ]
  • N2-(5-(1-(aminomethyl)cyclohexyl)-2-methoxyphenyl)-5-chloro-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydroxide; lithium aluminium tetrahydride / diethyl ether / 4 h / 0 - 20 °C 1.2: 0.33 h / 0 °C 2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3.1: nitric acid; trifluoroacetic acid / 2 h / 0 °C 4.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h 5.1: hydrogenchloride / 2-ethoxy-ethanol / 15 h / 80 °C 6.1: potassium carbonate; water / ethanol / 15 h / 100 °C
  • 22
  • [ 36263-51-1 ]
  • [ 36970-20-4 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 1-(4-methoxyphenyl)cyclohexane carbonitrile With lithium aluminium tetrahydride; sodium hydroxide In diethyl ether at 0 - 20℃; for 4h; Stage #2: With sodium hydroxide In diethyl ether; water at 0℃; for 0.333333h; 2.2 Step 2: Preparation of(1 -(4-methoxyphenyl)cyclohexyl)methaneamine Lithium aluminum hydride (1.79 g, 47.38 mmol) was dissolved in diethylether (51 mL), to which diethylether (5 mL) solution containing 1-(4-methoxyphenyl)cyclopentane-1-carbonitrile (5.1 g, 23.69 mmol) prepared in step 1 was added at 0° C. The reaction mixture was stirred at room temperature for 4 hours. Water and 2 N sodium hydroxide aqueous solution were added thereto at 0° C. The reaction mixture was stirred for 20 minutes and the produced solid was filtered. The filtrate was dried over sodium sulfate, and then filtered. The solvent was eliminated by distillation under reduced pressure. Then, purification was performed by silica gel column chromatography (eluent: methanol/dichloromethane, 1/10) to give the target compound (1-(4-methoxyphenyl)cyclohexyl)methaneamine as a yellow solid (4.5 g, 20.517 mmol, yield: 87%). 1H-NMR (300 MHz, CDCl3) δ 7.24 (d, J=9.0 Hz, 2H), 6.89 (d, J=8.7 Hz, 2H), 3.80 (s, 3H), 2.65 (s, 2H), 2.06-2.11 (m, 2H), 1.35-1.53 (m, 8H); LC/MS 220.03 [M+H+].
  • 23
  • [ 36263-51-1 ]
  • 2,2,2-trifluoro-N-((1-(4-methoxy-3-nitrophenyl)cyclohexyl)methyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydroxide; lithium aluminium tetrahydride / diethyl ether / 4 h / 0 - 20 °C 1.2: 0.33 h / 0 °C 2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3.1: nitric acid; trifluoroacetic acid / 2 h / 0 °C
  • 24
  • [ 36263-51-1 ]
  • N-((1-(3-amino-4-methoxyphenyl)cyclohexyl)methyl)-2,2,2-trifluoroacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydroxide; lithium aluminium tetrahydride / diethyl ether / 4 h / 0 - 20 °C 1.2: 0.33 h / 0 °C 2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 3.1: nitric acid; trifluoroacetic acid / 2 h / 0 °C 4.1: palladium 10% on activated carbon; hydrogen / methanol / 4 h
  • 25
  • [ 36263-51-1 ]
  • 2,2,2-trifluoro-N-((1-(4-methoxyphenyl)cyclohexyl)methyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide; lithium aluminium tetrahydride / diethyl ether / 4 h / 0 - 20 °C 1.2: 0.33 h / 0 °C 2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
  • 26
  • [ 36263-51-1 ]
  • [ 56140-77-3 ]
YieldReaction ConditionsOperation in experiment
84% With sodium hydride; zinc(II) chloride In tetrahydrofuran; mineral oil at 40℃; for 4h; Inert atmosphere; Sealed tube; Reduction of Nitriles 1 and 3 to Aldehydes 2 and 4; General Procedure General procedure: To a mixture of NaH (60% dispersion in mineral oil; 60.0 mg, 1.50 mmol) and ZnCl2 (102 mg, 0.750 mmol) in a 25-mL sealed tube was added a solution of nitrile 1 or 3 (0.500 mmol) in THF (2.5 mL). The mixture was sealed and stirred at 40 °C. The reaction was quenchedby following one of the two protocols. Workup protocol 1: Upon full consumption of the nitrile (TLC or GC monitoring), silica gel (2.0 g) was added to the mixture and it was diluted with hexane (10 mL) at 0 °C. The resulting mixture was stirred for 1 h at 24 °C. The mixture was then filtered through layers of cottonand sand and washed with EtOAc. The volatile materials were removedin vacuo from the resulting filtrate. The crude residue was purified by flash column chromatography to give the corresponding aldehyde 2 or 4. Workup protocol 2: Upon full consumption of amide (TLC or GC monitoring), the reaction was quenched with pH 10 ammonium buffer at 0°C and the organic materials were extracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (MgSO4). The volatile materials were removed in vacuo and the resulting crude residue was purified by flash column chromatography to give the corresponding aldehyde 2 or 4.
  • 27
  • [ 36263-51-1 ]
  • 1-(4-methoxyphenyl)cyclohexanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate In dimethyl sulfoxide at 60℃; for 3h; 11.P2 P2. Weigh 14 g of 1-(4-methoxyphenyl)-1-cyclohexanecarbonitrile obtained in step P1, add 50 ml of dimethyl sulfoxide to dissolve, add 20.2 g of potassium carbonate, and under the condition of 20°C , add 10ml of hydrogen peroxide at a rate of 1ml/min, the mass fraction of hydrogen peroxide is 31%, heat up to 60°C at a rate of 10°C/min for 3 hours, and cool at 20°C after the reaction is completed. After cooling, add ice water to make The product was precipitated, filtered and washed with water to obtain 1-(4-methoxyphenyl)cyclohexanecarboxamide
  • 28
  • [ 36263-51-1 ]
  • [ 125802-09-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 3 h / 60 °C 2: sodium hydroxide; sodium chlorine monoxide / acetonitrile / 16 h / 0 - 20 °C / 760.05 Torr / pH 13
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