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[ CAS No. 870774-25-7 ] {[proInfo.proName]}

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Chemical Structure| 870774-25-7
Chemical Structure| 870774-25-7
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Quality Control of [ 870774-25-7 ]

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Product Details of [ 870774-25-7 ]

CAS No. :870774-25-7 MDL No. :MFCD08669639
Formula : C16H13BO2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :BQHVXFQXTOIMQM-UHFFFAOYSA-N
M.W : 248.08 Pubchem ID :44119399
Synonyms :

Calculated chemistry of [ 870774-25-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 79.21
TPSA : 40.46 ?2

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) : -5.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.7
Log Po/w (WLOGP) : 2.19
Log Po/w (MLOGP) : 2.72
Log Po/w (SILICOS-IT) : 1.93
Consensus Log Po/w : 2.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.2
Solubility : 0.0156 mg/ml ; 0.0000631 mol/l
Class : Moderately soluble
Log S (Ali) : -4.24
Solubility : 0.0143 mg/ml ; 0.0000575 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.49
Solubility : 0.00081 mg/ml ; 0.00000327 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.16

Safety of [ 870774-25-7 ]

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

Application In Synthesis of [ 870774-25-7 ]

* 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 [ 870774-25-7 ]

[ 870774-25-7 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 870774-25-7 ]
  • [ 1714-29-0 ]
  • 1-(4-naphthalene-1-yl-phenyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Heating / reflux; (Synthesis of Compound (AN-2)) (1) Synthesis of Intermediate [1-bromo-6-(4-naphthalene-1-yl-phenyl) pyrene] 7.4 g of 4-(naphthalene-1-yl) phenyl boronic acid prepared by a well known method and 7.0 g of conventional 1-bromopyrene were dissolved in 80 ml of dimethoxyethane (DME). Subsequently, 0.58 g of tetrakistriphenylphosphine palladium and 40 ml of 2M-sodium carbonate aqueous solution were added therein, followed by argon displacement. After heating and refluxing over 8 hours, it was stood to cool and then an organic layer was extracted therefrom by toluene. The organic layer was washed by saturated salt water, followed by drying through anhydrous sodium sulfate, and then the organic solvent was removed by an evaporator. The residue was refined through a silica gel chromatography (a developing solvent: toluene) and then 10.0 g of 1-(4-naphthalene-1-yl-phenyl) pyrene was obtained. (yield: 99 %) 10.0 g of 1-(4-naphthalene-1-yl-phenyl)pyrene obtained was dispersed into 100 ml of dimethyl formaldehyde (DMF), and 5.3 g N-bromosuccinamide (NBS) in DMF solution was dropped therein at room temperature. After stirred over 5 hours, it was left around overnight. After the overnight, 150 ml of water was added to it and the deposited crystal was filtrated, followed by water and ethanol washing of the crystal. The crystal obtained was refined through a silica gel chromatography (a developing solvent: hexane / toluene = 2 / 1) and then 4.5 g of 1-bromo-6-(4-naphthalene-1-yl-phenyl)pyrene (the yield: 38%) and 3.8 g of 1-bromo-8-(4-naphthalene-1-yl-phenyl)pyrene were obtained (the yield: 32%) as the intermediates.
  • 2
  • [ 5419-55-6 ]
  • [ 204530-94-9 ]
  • [ 870774-25-7 ]
YieldReaction ConditionsOperation in experiment
67% With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; toluene; (8) Synthesis of Compound 2-8 Under an argon gas atmosphere, a mixture of 208.8 g (737.4 mmol) of 1-(4-bromophenyl) naphthalene and 2.1 L of dehydrated THF was cooled down to -60 degrees C., and added with 567 mL (884.9 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for two hours at -60 degree C. 416 g (2.21 mol) of triisopropyl borate was dropped into the reaction solution at -60 degrees C. Subsequently, the reaction mixture was stirred for 17 hours at room temperature. The reaction mixture was further added with solution of hydrochloric acid to be stirred for one hour at room temperature. After the reaction, the reaction mixture was further added with toluene, so that aqueous phase thereof was eliminated. After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid by toluene, 126 g of 4-(1-naphthyl) phenylboronic acid was obtained at an yield of 67%.
  • 3
  • [ 870774-25-7 ]
  • [ 605-02-7 ]
  • 4
  • [ 870774-25-7 ]
  • [ 1196690-48-8 ]
  • [ 1196690-50-2 ]
YieldReaction ConditionsOperation in experiment
94% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃; for 18h;Inert atmosphere; Example 7; In Example 7, a synthesis method of 2-(4-{10-[4-(1-naphthyl)phenyl]-9-anthryl}phenyl)benzoxazole (abbrev.: NPhABOx) represented by Structural Formula (131) will be described. [Step 1: Synthesis of 2-(4-{10-[4-(1-naphthyl)phenyl]-9-anthryl}phenyl)benzoxazole] A synthesis scheme of 2-(4-{10-[4-(1-naphthyl)phenyl]-9-anthryl}phenyl)benzoxazole is shown in (F-1). In a 50 mL three-neck flask, 0.97 g (2.2 mmol) of 2-[4-(10-bromo-9-anthryl)phenyl]benzoxazole, 0.57 g (2.3 mmol) of 4-(1-naphthyl)phenylboronic acid, 0.46 g (4.3 mmol) of sodium carbonate, 15 mL of toluene, 3 mL of ethanol, and 3 mL of water were placed. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture, 35 mg (0.030 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was stirred under nitrogen stream at 100 C. for 18 hours. After a certain period, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extracted solution and the organic layer were combined and washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and the organic layer was dried with magnesium sulfate. The mixture was gravity filtered, and the obtained filtrate was condensed to give a solid. The solid was purified by silica gel column chromatograghy (toluene:hexane=2:1) and recrystallized with toluene/hexane, giving 1.2 g of the target white powder in a yield of 94%. Then, 1.2 g of the target substance was subjected to sublimation purification at 385 C. under argon stream (flow rate: 3.0 mL/min) and a pressure of 10 Pa for 15 hours; thus, 1.1 g of the target substance was recovered in a yield of 91%. This compound was measured by nuclear magnetic resonance (NMR) spectrometry and identified as 2-(4-{10-[4-(1-naphthyl)phenyl]-9-anthryl}phenyl)benzoxazole (abbrev.: NPhABOx). The 1H NMR data is shown below. 1H NMR (300 MHz, CDCl3): delta (ppm)=7.38-7.47 (m, 6H), 7.55-7.78 (m, 13H), 7.84-7.99 (m, 5H), 8.17-8.20 (m, 1H), 8.53 (d, J=8.1 Hz, 2H).
  • 5
  • [ 870774-25-7 ]
  • [ 1204427-12-2 ]
  • [ 1204427-16-6 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate; tris-(o-tolyl)phosphine;palladium diacetate; In ethanol; water; toluene; at 80℃; for 5h;Inert atmosphere; In a 200 mL three neck flask were put 2.5 g (4.4 mmol) of 3-bromo-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole, 1.1 g (4.4 mmol) of 4-(1-naphthyl)phenylboronic acid, and 0.33 g (1.1 mmol) of tri(ortho-tolyl)phosphine. The atmosphere in the flask was replaced with nitrogen. To this mixture were added 5.0 mL of an aqueous potassium carbonate solution (2.0 mol/L), 60 mL of toluene, and 20 mL of ethanol. This mixture was stirred to be degassed while the pressure was reduced. To this mixture was added 49 mg (0.22 mmol) of palladium(II) acetate. This mixture was stirred under a nitrogen stream at 80 C. for 5 hours.After being stirred, the mixture was separated into an aqueous layer and an organic layer. The aqueous layer was extracted with toluene. The extract and the organic layer were combined and washed with saturated brine. Then, the organic layer was dried with magnesium sulfate, followed by gravity filtration of this mixture. An oily substance obtained by concentration of the resulting filtrate was dissolved in about 10 mL of toluene. This solution was suction filtered through Celite (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). An oily substance obtained by concentration of the resulting filtrate was purified by silica gel column chromatography (the developing solvent was a mixed solvent of a 5:1 ratio of hexane to toluene) to give a light yellow oily substance.This oily substance was recrystallized with a mixed solvent of toluene and hexane to give the desired substance as 2.4 g of a light yellow powder in a yield of 79%. Sublimation purification of 2.3 g of the light yellow powder obtained was performed by a train sublimation method. The light yellow powder was heated at 340 C. with an argon flow rate of 4.0 mL/min under reduced pressure. After the sublimation purification, 2.2 g of a light yellow solid which was the desired substance was obtained in a yield of 95%. By a nuclear magnetic resonance (NMR) method, this compound was confirmed to be 3-[4-(1-naphthyl)phenyl]-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPAalphaNP) which was the desired compound.The following are data of the 1H NMR measurement of the compound obtained: 1H NMR (CDCl3, 300 MHz):delta=7.37-7.67 (m, 17H), 7.70-7.80 (m, 6H), 7.85-7.96 (m, 9H), 8.06 (d, J=8.1 Hz, 1H), 8.29 (d, J=7.8 Hz, 1H), 8.52 (d, J=0.90 Hz, 1H)In addition, FIGS. 18A and 18B show 1H NMR charts. Note that FIG. 18B is a chart showing an enlarged part in the range of 7.2 ppm to 8.4 ppm in FIG. 18A.
With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In ethanol; water; toluene; at 80℃; for 5h;Inert atmosphere; Into a 200 mL three-neck flask were put 2.5 g (4.4 mmol) of 3-bromo-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole, 1.1 g (4.4 mmol) of 4-(l-naphthyl)phenylboronic acid, and 0.33 g (1.1 mmol) of tri(ortho-tolyl)phosphine , and the air in the flask was replaced with nitrogen. To this mixture were added 5.0 mL (2.0 mol/L) of a potassium carbonate aqueous solution, 60 mL of toluene, and 20 mL of ethanol. This mixture was stirred to be degassed while the pressure was reduced. To the mixture was added 49 mg (0.22 mmol) of palladium(II) acetate, and the mixture was stirred at 80 0C under a nitrogen stream for 5 hours. After the stir, the aqueous layer of the mixture was extracted with toluene and the extracted solution and the organic layer were washed together with saturated saline. After that, the organic layer was dried with magnesium sulfate, and this mixture was subjected to gravity filtration. The obtained filtrate was concentrated to give an oily substance. The obtained oily substance was dissolved in about 10 mL of toluene. This solution was subjected to suction filtration through Celite (Catalog No. 531-16855, manufactured by Wako Pure Chemical Industries, Ltd.), alumina, and Florisil (Catalog No. 540-00135, manufactured by Wako Pure Chemical Industries, Ltd.). The obtained filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (a developing solvent was a mixed solvent of hexane and toluene (hexane: toluene= 5: I)) to give a light yellow oily substance. The oily substance was recrystallized with a mixed solvent of toluene and hexane to give 2.4 g of light yellow powder, which was the object, at a yield of 79%[0476]Sublimation purification by train sublimation was performed on 2.3 g of the obtained light yellow powder. The sublimation purification was performed under such conditions that the light yellow powder was heated at 340 0C with an argon gas applied at a flow rate of 4.0 mL/min under reduced pressure. After the sublimation purification, 2.2 g of a light yellow solid, which was the objective compound, was obtained at a yield of 95%. [0477]This compound was identified as3-[4-(l-naphthyl)phenyl]-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (CzPAaNP) which was the object by nuclear magnetic resonance (NMR). 1H NMR data of the obtained compound is shown below. 1H NMR(CDCl3, 300 MHz): d= 7.37-7.67(m, 17H), 7.70-7.80(m, 6H), 7.85-7.96(m, 9H), 8.06(d, J= 8.1 Hz, IH), 8.29(d, J= 7.8 Hz,IH), 8.52(d, J= 0.90 Hz, IH)[0478]Further, the 1H NMR chart is illustrated in FIGS. 52A and 52B. Note that FIG.52B is a chart showing an enlarged portion of FIG. 52A in the range of from 7.2 ppm to 8.4 ppm.
  • 6
  • [ 870774-25-7 ]
  • C33H19Br [ No CAS ]
  • [ 1220509-81-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 80℃; (2-3) Synthesis of Compound 35; 4 g of Intermediate 11, 2.3 g of 4-(l~naphthalene)-l-phenylboronic acid, 40 ml of tetrahydrofuran, 2.5 g of potassium carbonate and 20 ml of water were mixed in a 100 ml round-bottom flask with stirring. 0.53 g of tetrakis(triphenylphosphine)palladium(0) was added to the mixture, which was heated to 80 C . The reaction solution was cooled and filtered, and the precipitated crystals were washed with acetone and subjected to recrystalization with methylene chloride, to obtain 2 g of the title compound. 1H-NMR(CDCl3, 500MHz) (IH, d, 8.48532, 8.46735), (IH, d, 8.41562, 8.40007), (IH, d, 8.07572, 8.05957), (2H, d, 7.99909, 7.98380), (3H, m, 7.94149-7.88387), (IH, d, 7.83335, 7.81698), (6H, m,7.71184-7.61582), (4H, m5 7.56625 -7.48845), (2H, t, 7.4.551 -7.37579), (IH, t, 7.19805 -7.16625), (IH, t, 7.15543 -7.12234), (3H, t, 7.10562, 7.07492), (2H, d, 7.02127 -7.00615), (IH, t, 6.84303 -6.81196), (IH, d, 6.62948, 6.61470) EI-MS : m/z 618(M+)
  • 7
  • [ 870774-25-7 ]
  • 3-bromo-10-phenylspiro[benzo[ij]tetraphene-7,9'-fluorene] [ No CAS ]
  • [ 1220509-86-3 ]
YieldReaction ConditionsOperation in experiment
81% With tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; for 0.5h; General procedure: A solution of 3-bromo-10-phenylspiro[benzo[ij]tetraphene-7,9'-fluorene] (5.71 g, 10 mmol), tetrakis(triphenylphosphine)palladium(0) (0.59 g, 0.51 mmol), and naphthalene-1-boronic acid (1.72 g, 10 mmol) dissolved in THF (150 mL) was stirred in a double-necked flask for 30 min. Potassium carbonate (2 M, 150 mL) was added dropwise over 20 min. The resulting reaction mixture was refluxed overnight at 80C and then extracted with ethyl acetate and water. After the organic layer was evaporated with a rotary evaporator, the resulting powdery product was purified by column chromatography from dichloromethane/n-hexane (1/1) to give the yellow 1N-PSBTF crystalline product. 2N-PSBTF and NP-PSBTF were prepared using similar procedures described above.
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 80℃; (3-5) Synthesis of Compound 110; 1.6 g of Intermediate 12, 0.86 g of 4-(l -naphthalene)- 1-phenylboronic acid, 20 ml of tetrahydrofuran, 1 g of potassium carbonate and 10 ml of water were mixed in a 100 ml round-bottom flask with stirring. 0.2 g of tetrakis(triphenylphosphine)palladium(0) was added to the mixture, which was heated to 80 C . The reaction solution was cooled and filtered, and the precipitated crystals were washed with acetone and subjected to recrystalization with methylene chloride, to obtain 1.5 g of the title compound. 1H-NMR(CDCl3, 500MHz) (IH, d, 8.50970-8.49168), (IH, d, 8.42353, 8.4.794), (IH, d, 8.07996, 8.06194), (2H, d, 8.01643, 8.00113), (IH, d, 7.98321, 7.96542), (3H, m, 7.94593-7.89355), (IH, d, 7.84365, 7.82718), (5H, m, 7.69204-7.61719), (6H, d, 7.58142-7.47368), (4H, m, 7.41957-7.35884), (IH, t, 7.30467-7.27303), (5H, m, 7.16011-7.09383), (2H, d, 7.05529, 7.04019), (IH, d, 6.64619, 6.63128) EI-MS : m/z 695(M+)
  • 8
  • [ 870774-25-7 ]
  • [ 1220510-00-8 ]
  • [ 1220510-02-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 80℃; (5-6) Synthesis of Compound 260; 1O g of Intermediate 16, 4.7 g of 4-(l -naphthalene)- 1-phenylboronic acid, 100 ml of tetrahydrofuran, 3.9 g of potassium carbonate and 40 ml of water were mixed in a 100 ml round-bottom flask with stirring. 1.1 g of tetrakis(triphenylphosphine)palladium(0) was added to the mixture, which was heated to 80 C . The reaction solution was cooled and filtered, and the precipitated crystals were washed with acetone and subjected to recrystalization with methylene chloride, to obtain 12 g of the title compound. 1H-NMR(CDCl3, 500MHz) lH(d, 8.48257-8.46562), lH(d, 8.40254-8.38596), lH(d, 8.05832-8.04220), 2H(d, 8.00324-7.98666), lH(d, 7.97954-7.96394), 3H(m, 94291-7.88471), lH(d, 7.86588-7.84936), 5H(m, 7.60124-7.61055), 6H(m, 7.56555-7.48242), 4H(m, 7.44577-7.38305), lH(t, 7.31357-7.29255), 4H(7.18356-7.12363), lH(d, 7.09144-7.07529), lH(d, 6.65264-6.63775), 3H(s, 2.68341) EI-MS : m/z 709(M+)
  • 9
  • [ 870774-25-7 ]
  • [ 106-40-1 ]
  • [ 1222561-66-1 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In ethanol; water; toluene; at 60 - 80℃; for 1.5h;Inert atmosphere; Step 1: Synthesis of 4'-(1-naphthyl)biphenyl-4-amine To a 50 mL three-neck flask were added 0.70 g (4 mmol) of 4-bromoaniline, 1.0 g (4 mmol) of 4-(1-naphthyl)phenylboronic acid, and 61.8 mg (0.2 mmol) of tris(o-tolyl)phosphine, and nitrogen substitution in the flask was carried out. To the mixture were added 14 mL of toluene, 6 mL of ethanol, and 4 mL of an aqueous solution of potassium carbonate (2 mol/L). The mixture was stirred to be degassed under a reduced pressure, and then the mixture was heated at 60 C., which was followed by addition of 11.9 mg (0.05 mmol) of palladium(II) acetate. This mixture was stirred at 80 C. for 1.5 hours. After the reaction, toluene and water were added to the mixture, the organic layer and the aqueous layer were separated from each other, and the aqueous layer was extracted twice with toluene. The obtained extract and the organic layer were combined, washed with brine, and dried with magnesium sulfate. The mixture was subjected to gravity filtration to remove magnesium sulfate, and the filtrate was concentrated to obtain an oily product. The oily product was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina, resulting in a filtrate. The filtrate obtained was concentrated to give 1.1 g of an oily substance which was a target substance in 95% yield. The synthetic scheme of 4'-(1-naphthyl)biphenyl-4-amine is shown in (B-1).
  • 10
  • [ 870774-25-7 ]
  • (R)-2,6-dibromo-4H-dinaphtho[2,1-d:1',2'-f][1,3,2]dithiazepine-3,3,5,5-tetraoxide [ No CAS ]
  • C52H33NO4S2 [ No CAS ]
  • 11
  • [ 870774-25-7 ]
  • [ 1564-64-3 ]
  • [ 1092390-00-5 ]
YieldReaction ConditionsOperation in experiment
92% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In toluene; for 12h;Inert atmosphere; Reflux; d. Preparation of Intermediate IInto a RBF (5000 mL) was added 9-bromoanthracene (100 g, 0.389 mol), 4-(Naphthalene-1-yl) Phenyl boronic acid (116 g, 0.469 mol), followed by the addition of toluene (3000 mL). The mixture was purged with N2 for 10 min. Then Na2CO3 (124 g, 1.167 mole) dissolved in the water (600 mL) was added. The mixture was continued to be purged with N2 for 10 min. A catalytic amount of Pd(PPh3)4 (2.3 g, 1.95 mmole) was added. The mixture was refluxed under N2 for 12 h. Cooled down the reaction mixture to 40 C., filtered, separated off water layer, and concentrate the organic phase to a final volume (150 ml) to obtain the solid of intermediate I (131 g, yield: 92%). C30H2O: El, MS m/z (%): 380 (100, M+).
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