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[ CAS No. 287944-16-5 ] {[proInfo.proName]}

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Chemical Structure| 287944-16-5
Chemical Structure| 287944-16-5
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Product Details of [ 287944-16-5 ]

CAS No. :287944-16-5 MDL No. :MFCD11052631
Formula : C11H19BO3 Boiling Point : No data available
Linear Structure Formula :OC5H7BO2C2(CH3)4 InChI Key :DOSGEBYQRMBTGS-UHFFFAOYSA-N
M.W : 210.08 Pubchem ID :11218053
Synonyms :
Chemical Name :3,6-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyran

Calculated chemistry of [ 287944-16-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.82
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 60.43
TPSA : 27.69 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.31
Log Po/w (WLOGP) : 1.96
Log Po/w (MLOGP) : 0.79
Log Po/w (SILICOS-IT) : 1.33
Consensus Log Po/w : 1.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.9
Solubility : 2.63 mg/ml ; 0.0125 mol/l
Class : Very soluble
Log S (Ali) : -1.49
Solubility : 6.77 mg/ml ; 0.0322 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.37
Solubility : 0.907 mg/ml ; 0.00432 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.78

Safety of [ 287944-16-5 ]

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

Application In Synthesis of [ 287944-16-5 ]

* 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 [ 287944-16-5 ]

[ 287944-16-5 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 67515-59-7 ]
  • [ 287944-16-5 ]
  • [ 1241910-67-7 ]
YieldReaction ConditionsOperation in experiment
59% With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 20h;Inert atmosphere; Reflux; sealed tube; In a screw cap pressure tube, <strong>[67515-59-7]4-fluoro-3-(trifluoromethyl)-benzonitrile</strong> (425 mg, 1.70 mmol) and 2-(3,6-dihydro-2Eta-pyran-4-yl)-4,4,5,5-tetramethyl- 1,3,2- dioxaborolane (357.1 mg, 1.70 mmol) were dissolved in dimethoxyethane. Na2CO3 (2 M aq. sin, 2.5 ml) and LiCl (216.4 mg, 5.1 mmol) were added. N2 was bubbled through the mixture for 5 minutes. Pd(PPtLs)4 (39.3 mg, 0.03 mmol) was added. The tube was sealed and the mixture heated to reflux for 20 h. The mixture was allowed to cool. H2O was added and the product extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography; Pet. Ether, EtOAc (4:1) affording 254 mg (59%) the title compound. 1H NMR (CDCl3) delta 7.97 (d, IH), 7.80 (dd, IH), 7.40 (d, IH), 5.72 (m, IH), 4.29 (dd, 2H), 3.92 (t, 2H), 2.36 (m, 2H).
59% With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 20h;Inert atmosphere; Sealed; Reflux; 4-(3,6-Dihydro-2H-pyran-4-yl)-3-(trifluoromethyl)benzonitrile In a screw cap pressure tube, <strong>[67515-59-7]4-fluoro-3-(trifluoromethyl)-benzonitrile</strong> (425 mg, 1.70 mmol) and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (357.1 mg, 1.70 mmol) were dissolved in dimethoxyethane. Na2CO3 (2 M aq. sln, 2.5 ml) and LiCl (216.4 mg, 5.1 mmol) were added. N2 was bubbled through the mixture for 5 minutes. Pd(PPh3)4 (39.3 mg, 0.03 mmol) was added. The tube was sealed and the mixture heated to reflux for 20 h. The mixture was allowed to cool. H2O was added and the product extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography; Pet. Ether, EtOAc (4:1) affording 254 mg (59%) the title compound. 1H NMR (CDCl3) delta 7.97 (d, 1H), 7.80 (dd, 1H), 7.40 (d, 1H), 5.72 (m, 1H), 4.29 (dd, 2H), 3.92 (t, 2H), 2.36 (m, 2H).
  • 2
  • [ 100189-84-2 ]
  • [ 287944-16-5 ]
  • [ 1458654-82-4 ]
  • [ 1458654-84-6 ]
  • 3
  • [ 100189-84-2 ]
  • [ 287944-16-5 ]
  • 4-(4-bromo-3,5-dimethylphenyl)-3,6-dihydro-2H-pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
404 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In water; toluene; at 60℃; for 12h;Inert atmosphere; Sealed tube; Step 1: 4-(4-Bromo-3,5-dimethylphenyl)-3,6-dihydro-2H-pyran [0725] In a microwave vial <strong>[100189-84-2]2,5-dibromo-1,3-dimethylbenzene</strong> (800 mg), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (640 mg) and K3PO4 (1.3 g) are suspended in toluene (12 mL) and water (1.2 mL) and purged for 10 minutes with argon. [1,1?-Bis(diphenylphosphino)-ferrocene]-dichloropalladium-(II) (100 mg) is added, the vial is sealed and the mixture is stirred at 60 C. for 12 hours. After cooling to room temperature the mixture is diluted with diethylether and washed with saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1?60:40) to give the title compound. Yield: 404 mg.
404 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In water; toluene; at 60℃; for 12h;Inert atmosphere; Microwave irradiation; In a microwave vial 2,5-dibromo-1 ,3-dimethylbenzene (800 mg), 2-(3,6-dihydro-2H- pyran-4-yl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (640 mg) and K3PO (1 .3 g) are suspended in toluene (12 ml_) and water (1 .2 ml_) and purged for 10 minutes with argon. [1 ,1 '-Bis(diphenylphosphino)-ferrocene]-dichloropalladium-( l l ) (100 mg) is added, the vial is sealed and the mixture is stirred at 60C for 12 hours. After cooling to room temperature the mixture is d iluted with diethylether and washed with saturated aqueous NH CI solution. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1?60:40) to give the title compound. Yield: 404 mg.
  • 4
  • [ 65202-50-8 ]
  • [ 287944-16-5 ]
  • 6-(3,6-Dihydro-2H-pyran-4-yl)pyridazine-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.2% With tetrakis(triphenylphosphine) palladium(0); water; caesium carbonate; In 1,4-dioxane; at 125℃; for 0.5h;Microwave irradiation; INTERMEDIATE 63 6-(3,6-Dihydro-2H-pyran-4-yl)pyri zine-3-carboxylic acid Methyl 6-chloropyridazine-3-carboxylate (1.00g, 5.79mmol), 4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (1.22g, 5.79mmol), Pd(PPh3)4 (536mg, 0.464mmol) and CS2CO3 (3.40g, 10.4mmol) were suspended in dioxane (8mL) and water (8mL) and heated in a microwave reactor at 125°C for 30min. 1 M aq. HCI (10ml_) was added, the precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was passed through a silica pad eluting with 30percent MeOH in DCM and concentrated in vacuo to give the title compound as a white solid (946mg, 79.2percent). LCMS (ES+): 207.1 [MH]+. HPLC: Rt 3.30min, 49.9percent purity.
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; at 125℃; for 0.5h;Microwave irradiation; 6-(3,6-Dihydro-2H-pyran-4-yl)pyridazin-3-carboxylic Acid Methyl 6-chloropyridazine-3-carboxylate (1.00 g, 5.79 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (1.22 g, 5.79 mmol), Pd(PPh3)4 (536 mg, 0.44 mmol) and Cs2CO3 (3.40 g, 10.4 mmol) were suspended in dioxane (8 mL) and water (8 mL) and heated in a microwave reactor at 125° C. for 30 min. 1M aq HCl (10 mL) was added, the precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was passed through a silica pad eluting with 30percent MeOH in DCM and concentrated in vacuo to give the title compound as a white solid (946 mg, 79.2percent). LCMS (ES+): 207.1 [MH]+. HPLC: Rt 3.30 min, 49.9percent purity.
In 1,4-dioxane; water; 6-(3,6-Dihydro-2H-pyran-4-yl)pyridazine-3-carboxylic acid Methyl 6-chloropyridazine-3-carboxylate (1.00 g, 5.79 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (1.22 g, 5.79 mmol), Pd(PPh3)4 (536 mg, 0.464 mmol) and Cs2CO3 (3.40 g, 10.4 mmol) were suspended in dioxane (8 mL) and water (8 mL) and heated in a microwave reactor at 125° C. for 30 min. 1M aq. HCl (10 mL) was added, the precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was passed through a silica pad eluting with 30percent MeOH in DCM and concentrated in vacuo to give the title compound as a white solid (946 mg, 79.2percent). LCMS (ES+): 207.1 [MH]+. HPLC: Rt 3.30 min, 49.9percent purity.
  • 5
  • [ 360576-01-8 ]
  • [ 287944-16-5 ]
  • methyl 6-(3,6-dihydro-2H-pyran-4-yl)benzo[b]thiophene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 101℃; for 48.0h;Inert atmosphere; To a solution of methyl 6-bromobenzothiophene-2-carboxylate (1.0 g, 3.7 mmol) in dioxane (30 mL) and H20 (6 mL) under nitrogen was added K2C03 (1.5 g, 11 mmol), Pd(dppf)Cl2 CH2C12 (301 mg, 0.37 mmol) and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane (930 mg, 4.4 mmol). The mixture was stirred at 101 C for 48 hours. On completion, the reaction mixture was evaporated and purified by silica gel chromatography (petroleum ether: ethyl acetate = 16 : 1) to give compound B-165 (300 mg, 60% yield) as a white solid. i-NMR (CDC13, 400 MHz): delta 8.04 (s, 1H), 7.83 (d, J=8.4 Hz, 2H), 7.51-7.48 (m, 1H), 6.28 (d, J=1.6 Hz, 1H), 4.38-4.36 (m, 2H), 3.99-3.96 (m, 2H), 3.95 (s, 3H), 2.62-2.59 (m, 2H).
  • 6
  • [ 1000340-39-5 ]
  • [ 287944-16-5 ]
  • 4-chloro-3-(3,6-dihydro-2H-pyran-4-yl)-1H-pyrrolo[ 2,3-b]pyridine [ No CAS ]
  • 7
  • [ 615-55-4 ]
  • [ 287944-16-5 ]
  • 3,4-bis(3,6-dihydro-2H-pyran-4-yl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 130℃; for 0.5h;Microwave irradiation; A mixture of <strong>[615-55-4]3,4-dibromoaniline</strong> (220 mg, 0.8768 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (approximately 405.2 mg, 1.929 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (approximately 35.45 mg, 0.04384 mmol) and an aqueous solution of sodium carbonate (approximately 1.315 mL of 2 M, 2.630 mmol) in 1,4-dioxane (3 mL) was purged with nitrogen for 1 minute and then microwaved at 130 C for 30 minutes. The reaction mixture was diluted with dichloromethane, methanol and filtered through Florisil (5 g). The filtrate was concentrated to dryness under reduced pressure. The crude was purified by silica gel chromatography (12 g column; 10-100% ethyl acetate/hexane) to give 3,4-bis(3,6-dihydro-2H-pyran-4-yl)aniline (210 mg, 0.8161 mmol, 93.09). NMR (300 MHz, CDC13) delta 6.99 (d, J = 8.1 Hz, 1H), 6.60 (dd, J = 8.1, 2.5 Hz, 1H), 6.52 (d, J = 2.4 Hz, 1H), 5.75 (tt, J = 2.8, 1.6 Hz, 1H), 5.70 (tt, J = 2.8, 1.6 Hz, 1H), 4.32 - 4.24 (m, 4H), 3.87 (t, J = 5.4 Hz, 4H), 3.68 (s, 2H), 2.37 (qt, J = 5.4, 2.8 Hz, 4H) ppm. ESI-MS m/z calc. 257.14157, found 258.38 (M+l)+; Retention time: 0.55 minutes.
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