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[ CAS No. 1071547-23-3 ] {[proInfo.proName]}

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Chemical Structure| 1071547-23-3
Chemical Structure| 1071547-23-3
Structure of 1071547-23-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1071547-23-3 ]

CAS No. :1071547-23-3 MDL No. :N/A
Formula : C30H29BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :CMINGHZWIUHIMO-UHFFFAOYSA-N
M.W : 497.47 Pubchem ID :141466000
Synonyms :

Calculated chemistry of [ 1071547-23-3 ]

Physicochemical Properties

Num. heavy atoms : 33
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.13
Num. rotatable bonds : 6
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 146.9
TPSA : 6.48 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.84
Log Po/w (XLOGP3) : 8.9
Log Po/w (WLOGP) : 7.59
Log Po/w (MLOGP) : 6.49
Log Po/w (SILICOS-IT) : 6.72
Consensus Log Po/w : 6.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -8.67
Solubility : 0.00000106 mg/ml ; 0.0000000021 mol/l
Class : Poorly soluble
Log S (Ali) : -8.92
Solubility : 0.000000594 mg/ml ; 0.0000000012 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -10.94
Solubility : 0.0000000058 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.25

Safety of [ 1071547-23-3 ]

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

Application In Synthesis of [ 1071547-23-3 ]

* 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 [ 1071547-23-3 ]

[ 1071547-23-3 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 1071547-23-3 ]
  • [ 33513-42-7 ]
  • [ 1582284-49-8 ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: 4,4′-(2-(4-bromophenyl)-2-phenylethene-1,1-diyl)bis(N,N-dimethylaniline) With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; cyclohexane at -78 - 20℃;
Stage #1: 4,4′-(2-(4-bromophenyl)-2-phenylethene-1,1-diyl)bis(N,N-dimethylaniline) With n-butyllithium In tetrahydrofuran Stage #2: N,N-dimethyl-formamide In tetrahydrofuran
Stage #1: 4,4′-(2-(4-bromophenyl)-2-phenylethene-1,1-diyl)bis(N,N-dimethylaniline) With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: N,N-dimethyl-formamide at 20℃; for 2h; 2.3. Synthesis Under N2 atmosphere, a three-necked flask equipped with a magnetic stirrer was charged with zinc powder (4.2 g, 65 mmol)and 40 mL THF. The mixture was cooled to -5-0 °C, and TiCl4 (3.6 mL, 32.4 mmol) was slowly added by a syringe with the temperature kept under 10 °C. The suspending mixture was warmed to room temperature and stirred for 0.5 h, then heated at reflux for 2.5 h. The mixture was again cooled to -5-0 °C, charged with pyridine (0.24 mL, 3 mmol) and stirred for 10 min. The solution of two carbonyl compounds (in 6:6 mmol to 6:7.2 mmol mole ratios, in 15 mL THF) was added slowly. After addition, the reaction mixture was heated at reflux until the carbonyl compounds were consumed (monitored by TLC). The reaction was quenched with10% Na2CO3 aqueous solution and taken up with CH2Cl2. The organic layer was collected and concentrated. The crude material was purified by flash chromatography to give the desired products.The 1-(4-bromophenyl)-1,2,2-triphenylethylene was solved inTHF, the added n-BuLi at -78 °C for 2 h, followed by addition of dimethylformamide, the crude material was kept at room temperaturefor 2 h. The mixture was quenched by water and purified by flash chromatography, gave the expected aldehyde. Knoevenagel reaction was taking place between the aldehyde and the cyano derivative under alkaline conditions. The mixture was purified by flash chromatography, gave the target molecular.
With n-butyllithium Inert atmosphere;

  • 2
  • [ 90-90-4 ]
  • [ 90-94-8 ]
  • [ 1071547-23-3 ]
YieldReaction ConditionsOperation in experiment
56% With pyridine; titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Reflux;
42% With titanium tetrachloride; zinc In tetrahydrofuran at -78℃; Inert atmosphere; Reflux;
42% With titanium tetrachloride; zinc In tetrahydrofuran at 78℃; for 12h; Inert atmosphere; [TPE-N2-Br2] General procedure: Michler's ketone (1 g, 3.726mmol), 4,4′-Dibromobenzophenone (1.2 g, 3.726mmol), and zinc powder (2.9 g, 44.71mmol) were mixed in freshly distilled cold tetrahydrofuran (THF, 20mL, 0°C), and titanium tetrachloride (TiCl4, 2.8mL) was added dropwise under an argon atmosphere with the rapid stirring of over 10min. The mixture was then slowly warmed up to 78°C with stirring, and the reaction was allowed to further proceed for 12h under reflux. After the reaction, the mixture was cooled to room temperature, and deionized water (DI H2O, 25mL) was added to quench the reaction. The resulting solution was filtered through a pad of celite to remove the remaining zinc powder. The filtrated solution was washed with ethyl acetate (EtOAc) and DI H2O. The collected organic extract was washed with brine and dried over anhydrous sodium sulfate (Na2SO4). The resulting residue was concentrated in vacuo and was purified by flash column chromatography (n-hex/EtOAc=9:1, v/v, TLC: Rf 0.5). TPE-N2-Br2 was collected with a 29% yield (bright yellow solid).
31% Stage #1: (4-bromophenyl)(phenyl)methanone; bis(p-dimethylaminophenyl)methanone With zinc In tetrahydrofuran at -70℃; Inert atmosphere; Cooling with acetone-dry ice; Stage #2: With titanium tetrachloride In tetrahydrofuran at -78 - 20℃; for 8h; Inert atmosphere; Cooling with acetone-dry ice;
With titanium tetrachloride; zinc In tetrahydrofuran
With pyridine; titanium tetrachloride; zinc In tetrahydrofuran Inert atmosphere; Reflux; 2.3. Synthesis Under N2 atmosphere, a three-necked flask equipped with a magnetic stirrer was charged with zinc powder (4.2 g, 65 mmol)and 40 mL THF. The mixture was cooled to -5-0 °C, and TiCl4 (3.6 mL, 32.4 mmol) was slowly added by a syringe with the temperature kept under 10 °C. The suspending mixture was warmed to room temperature and stirred for 0.5 h, then heated at reflux for 2.5 h. The mixture was again cooled to -5-0 °C, charged with pyridine (0.24 mL, 3 mmol) and stirred for 10 min. The solution of two carbonyl compounds (in 6:6 mmol to 6:7.2 mmol mole ratios, in 15 mL THF) was added slowly. After addition, the reaction mixture was heated at reflux until the carbonyl compounds were consumed (monitored by TLC). The reaction was quenched with10% Na2CO3 aqueous solution and taken up with CH2Cl2. The organic layer was collected and concentrated. The crude material was purified by flash chromatography to give the desired products.The 1-(4-bromophenyl)-1,2,2-triphenylethylene was solved inTHF, the added n-BuLi at -78 °C for 2 h, followed by addition of dimethylformamide, the crude material was kept at room temperaturefor 2 h. The mixture was quenched by water and purified by flash chromatography, gave the expected aldehyde. Knoevenagel reaction was taking place between the aldehyde and the cyano derivative under alkaline conditions. The mixture was purified by flash chromatography, gave the target molecular.
With titanium tetrachloride In tetrahydrofuran Inert atmosphere;
With titanium chloride; zinc In tetrahydrofuran

  • 3
  • [ 1071547-23-3 ]
  • [ 12125-02-9 ]
  • C30H31BN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 4,4′-(2-(4-bromophenyl)-2-phenylethene-1,1-diyl)bis(N,N-dimethylaniline) With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #3: ammonium chloride In tetrahydrofuran; hexane; water for 2h; Inert atmosphere;
  • 4
  • [ 1071547-23-3 ]
  • C60H58N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 1.3: 2 h / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / N,N-dimethyl-formamide / 24 h / Inert atmosphere; Reflux
  • 5
  • [ 1071547-23-3 ]
  • C30H31BN2O2 [ No CAS ]
  • C60H58N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide for 24h; Inert atmosphere; Reflux;
  • 6
  • [ 1071547-23-3 ]
  • C34H30N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran 2: ethanol / 12 h / Reflux
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C 1.2: 2 h / 20 °C 2.1: Alkaline conditions
  • 7
  • [ 127-19-5 ]
  • [ 1071547-23-3 ]
  • 1,2-bis(4-diethylaminophenyl)-1-(4-acetophenyl)-2-phenylethene [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 4,4′-(2-(4-bromophenyl)-2-phenylethene-1,1-diyl)bis(N,N-dimethylaniline) With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 2h; Inert atmosphere; Stage #2: N,N-dimethyl acetamide In tetrahydrofuran; cyclohexane at 20℃; for 2h; Inert atmosphere;
With n-butyllithium In tetrahydrofuran
  • 8
  • [ 1071547-23-3 ]
  • [ 73183-34-3 ]
  • C36H41BN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane; dichloromethane at 20 - 85℃; Inert atmosphere;
  • 9
  • [ 1071547-23-3 ]
  • C39H35N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C 1.2: 2 h / 20 °C 2.1: Alkaline conditions
  • 10
  • [ 1071547-23-3 ]
  • C41H33F6N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C 1.2: 2 h / 20 °C 2.1: Alkaline conditions
  • 11
  • [ 1071547-23-3 ]
  • C42H41N5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / Inert atmosphere 2: piperidine / dichloromethane; isopropyl alcohol / 50 °C / Inert atmosphere
  • 12
  • [ 1071547-23-3 ]
  • C37H37N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / Inert atmosphere 2: piperidine / dichloromethane / 20 °C / Inert atmosphere
  • 13
  • [ 1071547-23-3 ]
  • C38H40N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / Inert atmosphere 2: piperidine / dichloromethane / 60 °C / Inert atmosphere
  • 14
  • [ 100-43-6 ]
  • [ 1071547-23-3 ]
  • (E)-4,4'-(2-phenyl-2-(4-(2-(pyridin-4-yl)vinyl)phenyl)ethene-1,1-diyl)bis(N,N-dimethylaniline) [ No CAS ]
YieldReaction ConditionsOperation in experiment
53%
YieldReaction ConditionsOperation in experiment
58% With piperidine; titanium tetrachloride; zinc In tetrahydrofuran for 10h; Reflux; 1; 2; 3 Preparation of 1-(4-bromophenyl)-1,2,2-tristyrene/1-(4-Bromophenyl)-2,2-bis(4-methoxyphenyl)-1-styrene/1-(4-Bromophenyl)-2,2-bis(4-N,N-dimethylaminophenyl)-1-styrene/1-(4-Bromophenyl)-2,2-bis(4-N,N-dioctylaminophenyl)-1-styrene: General procedure: Zinc powder (1.2g, 18.2mmol) was added to the reactor, 50mL of tetrahydrofuran was dissolved, and titanium tetrachloride (1.0mL, 9.2mmol) was added dropwise at -78 °C, stirred for 1 hour and raised to room temperature to continue stirring for 3 hours. Then piperidine (1.6mL, 4.6mmol) was added, and after stirring for 20 minutes at room temperature. Add 4-bromobenzoylbenzene (1.2g, 4.7mmol) and benzophenone (0.7g, 3.6mmol)/4,4’-dimethoxybenzophenone (0.9g, 3.6mmol)/4,4’-bis(N,N-dimethylamino)benzophenone (1.0g, 3.6mmol)/4,4'-bis(N,N-dioctylamino)benzophenone (2.4g, 3.6mmol). The reaction was heated to reflux for 10 hours. After the reaction is over, extract with dichloromethane, dry with anhydrous magnesium sulfate, filter with suction, and spin dry. Carry out silica gel column chromatography with a developing solvent of dichloromethane/petroleum ether with a volume ratio of 5:1, Get separately1-(4-bromophenyl)-1,2,2-tristyrene/1-(4-bromophenyl)-2,2-bis(4-methoxyphenyl)-1-styrene/1-(4-bromophenyl)-2,2-bis(4-N,N-dimethylaminophenyl)-1-styrene/1-(4-bromophenyl)-2,2-bis(4-N,N-dioctylaminophenyl)-1-styrene.The yields are: 60%, 63%, 58%, 54%.
  • 16
  • [ 1071547-23-3 ]
  • [ 135884-31-0 ]
  • C39H41N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 10h; Heating; Inert atmosphere;
  • 17
  • [ 1071547-23-3 ]
  • C70H64N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 10 h / Heating; Inert atmosphere 2: sodium methylate / methanol / Reflux; Inert atmosphere 3: pyridine / dichloromethane / 2.67 h / -78 - 20 °C
  • 18
  • [ 1071547-23-3 ]
  • C34H33N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 10 h / Heating; Inert atmosphere 2: sodium methylate / methanol / Reflux; Inert atmosphere
  • 19
  • [ 1071547-23-3 ]
  • [ 5720-07-0 ]
  • C37H36N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 100℃; for 12h; Inert atmosphere; 2.1.4. Synthesis of T-O All reactions were performed in a round bottle that had been flamedriedunder an argon atmosphere (Fig. S1). 4,4’-(2-(4-bromophenyl)-2-phenylethene-1,1-diyl)bis(N,N-dimethylaniline) (T-Br, 30 mg, 0.0603mmol), 4-Methoxybenzeneboronic acid (13.74 mg, 0.0904 mmol), potassiumacetate (59.18 mg, 0.603 mmol), and 1,1′ -Bis(diphenylphosphino)ferrocene] dichloropalladium(II) (13.23 mg, 0.018 mmol) weremixed in 1,4-dioxane (1.5 mL). The mixture was slowly warmed up to100 °C and stirred for 12 h. The mixture was then cooled to roomtemperature and the reaction was quenched by adding DI H2O (3 mL).The resulting solution was extracted with DI H2O three times, then theorganic layer (EtOAc) was washed with brine and dried over anhydrousNa2SO4. The resulting residue was concentrated in vacuo. The residuewas purified by flash column chromatography (n-hex/EtOAc = 8:2, v/v),and T-O was collected with a 34% yield (yellowish solid). 1H NMR (500MHz, CDCl3): δ 2.88 (s, 12H), 3.82 (s, 3H), 6.45 (t, J = 7.4 Hz, 4H),6.88-6.94 (m, 6H), 7.05-7.12 (m, 7H), 7.29 (d, J = 8.6 Hz, 2H), 7.49 (d,J = 9.2 Hz, 2H); 13C NMR (125 MHz, CDCl3): δ 0.1, 1.1, 14.3, 21.2, 29.8,32.0, 40.5, 55.4, 60.5, 71.9, 76.9, 77.1, 77.4, 111.4, 111.5, 114.1, 125.6,125.7, 127.7, 127.8, 131.7, 132.0, 132.5, 132.7, 133.6, 136.5, 137.4,141.3, 143.8, 145.4, 148.8, 148.9, 158.9. HRMS (m/z): calcd forC37H36N2O, 524.2827; found, 524.2826. Melting point: 254.54 °C.
  • 20
  • [ 1071547-23-3 ]
  • [ 98-80-6 ]
  • [ 103268-58-2 ]
YieldReaction ConditionsOperation in experiment
32.1% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 100℃; for 12h; Inert atmosphere; 2.1.2. Synthesis of T-B The reactions were performed in a round bottom bottle that had beenflame-dried under an argon atmosphere (Fig. S1). 4,4’-(2-(4-bromophenyl)-2-phenylethene-1,1-diyl)bis(N,N-dimethylaniline) (T-Br, 30mg, 0.0603 mmol), phenylboronic acid (11.02 mg, 0.0904 mmol), potassiumacetate (59.18 mg, 0.603 mmol), and 1,1′ -Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (13.236 mg, 0.01809 mmol)were dissolved in 1,4-dioxane (1.5 mL). The mixture was then slowlywarmed up to 100 °C whilst stirring, and the reaction has further proceededfor 12 h. After that, the mixture was cooled to room temperatureand added with DI H2O (2 mL). The aqueous layer was extracted thrice,and the organic extract (EtOAc) was washed with brine and dried overanhydrous Na2SO4. The resulting residue was concentrated in vacuo.The residue was purified by flash column chromatography. (n-hex/EtOAc = 9:1, v/v), and the T-B was collected with a 32.1% yield(yellowish solid). 1H NMR (500 MHz, CDCl3): δ 2.89 (s, 12H), 6.46 (t, J= 6.3 Hz, 4H), 6.92 (dd, J = 14.9, 8.6 Hz, 4H), 7.05-7.14 (m, 8H),7.41-7.34 (m, 4H), 7.57 (d, J = 8.6 Hz, 2H); 13C NMR (125 MHz, CDCl3):δ 0.1, 29.8, 40.5, 76.6-77.4, 111.4, 125.6, 126.1, 126.9, 127.7, 128.7,131.7-132.7, 148.9. HRMS (m/z): calcd for C36H34N2, 494.2722; found,494.2725. Melting point: 255.38 °C.
  • 21
  • [ 1071547-23-3 ]
  • [ 1582-24-7 ]
  • C36H29F5N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 100℃; for 12h; Inert atmosphere; 2.1.3. Synthesis of AuP-2 The reactions were performed in a round bottle that had been flamedriedunder an argon atmosphere (Fig. S1). A mixture of 4,4’-(2-(4-bromophenyl)-2-phenylethene-1,1-diyl)bis(N,N-dimethylaniline) (T-Br,30 mg, 0.0603 mmol), pentafluorophenylboronic acid (12.77 mg,0.0603 mmol), potassium acetate (23 mg, 0.2412 mmol), and 1,1′ -Bis(diphenylphosphino)ferrocene] dichloropalladium(II) (2.20 mg,0.00301 mmol) was added into 1,4-dioxane (1 mL). The mixture wasthen slowly warmed up to 100 °C and stirred for 12 h. After being cooledto room temperature, the reaction was quenched by adding DI H2O (2mL). The resulting solution was extracted with DI H2O three times, andthen the organic layer (EtOAc) was washed with brine and dried overanhydrous Na2SO4. The resulting residue was concentrated in vacuo.The residue was purified by flash column chromatography (n-hex/EtOAc = 9:1, v/v), and AuP-2 was collected with a 34% yield (yellowishsolid). 1H NMR (500 MHz, CDCl3): δ 2.90 (t, J = 6.6 Hz, 12H), 6.45 (td, J= 8.9, 6.7 Hz, 4H), 6.86-6.92 (m, 5H), 7.01-7.14 (m, 7H), 7.20 (d, J =11.5 Hz, 1H); 13C NMR (125 MHz, CDCl3): δ 0.1, 1.1, 29.8, 30.0, 31.0,40.4, 76.9, 77.1, 77.4, 111.3, 111.5, 119.4, 125.8, 127.8, 130.8, 131.6,131.9, 132.0, 132.6, 132.6, 133.3, 149.0, 207.1. 19F NMR (500 MHz,CDCl3): δ 143.1 (s, 2F), 156.3 (s, 1F), 162.3 (s, 3F); HRMS (m/z):calcd for C36H29F5N2, 584.2250; found, 584.2251. Melting point:254.33 °C.
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