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[ CAS No. 355836-08-7 ] {[proInfo.proName]}

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Chemical Structure| 355836-08-7
Chemical Structure| 355836-08-7
Structure of 355836-08-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 355836-08-7 ]

CAS No. :355836-08-7 MDL No. :MFCD04037222
Formula : C9H13BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :UFFAFBPZFGAMJJ-UHFFFAOYSA-N
M.W : 180.01 Pubchem ID :21931520
Synonyms :

Calculated chemistry of [ 355836-08-7 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.69
TPSA : 49.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : -0.01
Log Po/w (MLOGP) : 0.65
Log Po/w (SILICOS-IT) : 0.18
Consensus Log Po/w : 0.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.13
Solubility : 1.34 mg/ml ; 0.00742 mol/l
Class : Soluble
Log S (Ali) : -2.18
Solubility : 1.18 mg/ml ; 0.00657 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.19
Solubility : 1.16 mg/ml ; 0.00647 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 355836-08-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 355836-08-7 ]

* 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 [ 355836-08-7 ]

[ 355836-08-7 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 1899-99-6 ]
  • [ 355836-08-7 ]
  • [ 360576-58-5 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine)palladium (0); In 1,2-dimethoxyethane; A. A solution of 2-chloro-4-methoxy-6-methyl-5-nitropyrimidine (305 mg, 1.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (33 mg; 2 mol %) in ethyleneglycol dimethyl ether (8 mL) is stirred at room temperature for 15 min, then <strong>[355836-08-7]2,4-dimethyl-6-methoxybenzeneboronic acid</strong> (1.76 mmol) and an aqueous solution of sodium carbonate (1.0 M, 4 mL) are added sequentially. The mixture is heated to 75 C. with stirring for 1.5 h, then diluted with 0.1 N sodium hydroxide and extracted twice with 1:1 hexane-ethyl ether. Combined extracts are dried (sodium sulfate), filtered, concentrated and chromatographed on silica (4:1 hexane-ether) to give 3-methoxy-2-(4-methoxy-6-methyl-5-nitropyrimidin-2-yl)- 1,5-dimethylbenzene (0.36 g): 1H NMR (CDCl3, 400 MHz) 2.08 (s, 3H), 2.35 (s, 3H), 2.58 (s, 3H), 3.7 (s, 3H), 4.05 (s, 3H), 6.65 (s, 1H), 6.72); MS (CI) 304.
  • 2
  • [ 355836-08-7 ]
  • (4-iodo-2,6-dimethyl-phenyl)-dipropyl-amine [ No CAS ]
  • (2'-methoxy-3,5,4',6'-tetramethyl-biphenyl-4-yl)-dipropyl-amine [ No CAS ]
  • 3
  • [ 95-89-6 ]
  • [ 355836-08-7 ]
  • [ 355836-13-4 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 70 - 75℃; 2-Methoxy-4,6-dimethylbenzeneboronic acid (1. 08g, 6.0 mmol) is added to a solution of 2-chloro-3,6-dimethylpyrazine (0. [71 G,] 5.0 mmol) and tetrakis (triphenylphosphine) palladium [(O)] (140 mg, 2.5 [MOL%)] in ethylene glycol dimethyl ether [(30] mL), followed by the addition of 1 M aqueous sodium carbonate solution (15 mL). The mixture is stirred at [70-75C] overnight, allowed to cool, diluted by saturated aqueous sodium bicarbonate solution, and extracted twice with [ET20.] Combined extracts are dried (sodium sulfate), filtered, and concentrated in vacuo. The residue is purified by filtration through a short pad of silica gel to give 1.4g of crude product.
  • 4
  • [ 475174-78-8 ]
  • [ 355836-08-7 ]
  • [ 475174-79-9 ]
YieldReaction ConditionsOperation in experiment
With barium dihydroxide;tetrakis(triphenylphosphine) palladium(0); In ethyleneglycol diethyl ether; water; at 80℃; for 0.5h; Production Example 11 2-Ethyl-4-methoxy-7-(2-methoxy-4,6-dimethylphenyl)-3-nitropyrazolo[1,5-a]pyridine After adding 4,6-dimethyl-2-methoxyphenylboric acid (191 mg), barium hydroxide octahydrate (334 mg) and tetrakis(triphenylphosphine)palladium (0) complex (123 mg) to a solution of 7-bromo-2-ethyl-4-methoxy-3-nitropyrazolo[1,5-a]pyridine (159 mg) in a mixture of ethyleneglycol diethyl ether (15 ML) and water (7.5 ML), the mixture was heated at 80C for 30 minutes.. water was added, extraction was performed with ethyl acetate, the extract was washed with saturated aqueous sodium hydrogencarbonate and brine and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure.. The residue was subjected to silica gel column chromatography (20 g), and the title compound (185 mg) was obtained from the n-hexane:ethyl acetate (5:1) fraction as yellow crystals.1H NMR (400MHz, CDCl3) delta 1.24 (t, J = 7.5 Hz, 3H), 1.98 (s, 3H), 2.40 (s, 3H), 2.99 (q, J = 7.5 Hz, 2H), 3.66 (s, 3H), 4.03 (s, 3H), 6.68 (s, 1H), 6.78 (s, 1H), 6.81 (d, J = 8.1 Hz, 1H), 6.90 (d, J = 8.1 Hz, 1H).
  • 5
  • [ 475174-85-7 ]
  • [ 355836-08-7 ]
  • [ 475174-84-6 ]
YieldReaction ConditionsOperation in experiment
With barium dihydroxide;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃; for 1h; After dissolving the obtained crude 7-bromo-2-methoxy-3-nitrosopyrazolo[1,5-a]pyridine, without further purification, in 1,2-dimethoxyethane (40 mL) and water (20 mL), 4,6-dimethyl-2-methoxyphenylboric acid (475 mg), tetrakis(triphenylphosphine)palladium (0) complex (203 mg) and barium hydroxide octahydrate (829 mg) were added and the mixture was heated and stirred at 80C for 1 hour. Water was added to the reaction mixture, extraction was performed with ethyl acetate, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and the title compound (200 mg) was obtained from the n-hexane:ethyl acetate (5:1) fraction as a brown oil.1H NMR (400MHz, CDCl3) delta 2.05 (s, 3H), 2.43 (s, 3H), 3.70 (s, 3H), 4.20 (s, 3H), 6.70 (s, 1H), 6.79 (s, 1H), 6.08 (dd, J = 1.6, 7.2 Hz, 1H), 7.80 (dd, J = 7.2, 8.4 Hz, 1H), 8.30 (dd, J = 1.6, 8.4 Hz, 1H).
  • 6
  • [ 446273-55-8 ]
  • [ 355836-08-7 ]
  • 1-[2-ethyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-a]pyrazin-3-yl]-1-butanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With barium dihydroxide;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 4h;Heating / reflux; 1-(8-Chloro-2-ethylimidazo[1,2-a]pyrazin-3-yl)-1-butanone (226 mg, 0.90 mmol) and <strong>[355836-08-7]4.6-dimethyl-2-methoxybenzeneboronic acid</strong> (198 mg, 1.1 mmol) were dissolved in a mixed solvent of 1,2-dimethoxyethane (4.5 mL) and water (0.75 mL) . Barium hydroxide octahydrate (347 mg, 1.1 mmol) and tetrakis(triphenylphosphine)palladium complex (79 mg, 0.068 mmol) were added thereto, and the mixture was heated under reflux for 4 hours under nitrogen atmosphere. After being allowed to cool, the reaction mixture was filtered and washed with ethyl acetate. Then, the filtrates were combined and washed with a 1N aqueous sodium hydroxide solution. It was extracted with ethyl acetate and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3) to give 1-[2-ethyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-a]pyrazin-3-yl]-1-butanone (245 mg) as a white amorphous. The resulting 1-[2-ethyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-a]pyrazin-3-yl]-1-butanone (220 mg, 0.63 mmol) was dissolved in tetrahydrofuran (2 mL), then a 0.90M propylmagnesium bromide solution in tetrahydrofuran (3.6 mL, 3.2 mmol) was added thereto under ice-cooling, and the mixture was stirred at room temperature for 2 hours. An aqueous saturated ammonium chloride solution was added to the reaction mixture, which was extracted with ethyl acetate and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=6:5) to give the title compound (150 mg) as white crystals. 1H NMR (400MHz, CDCl3) delta 0.87-0.96 (m, 6H), 1.18-1.45 (m, 4H), 1.25 (t, J = 7.5 Hz, 3H), 1.90-2.12 (m, 4H), 2.02 (s, 3H), 2.37 (s, 3H), 2.82 (q, J = 7.5 Hz, 2H), 3.68 (s, 3H), 6.68 (s, 1H), 6.74 (s, 1H), 7.81 (d, J = 4.9 Hz, 1H), 8.75 (d, J = 4.9 Hz, 1H).
  • 7
  • [ 28918-97-0 ]
  • [ 355836-08-7 ]
  • [ 478036-12-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine)palladium (0); In water; ethyl acetate; toluene; Step 1. Preparation of 4-Methoxy-2-(6-methoxy-2,4-dimethylphenyl)-6-methylpyrimidin-5-ol. A mixture of 2-chloro-4-methoxy-6-methylpyrimidin-5-ol (348 mg, 2.0 mmol), <strong>[355836-08-7]2-methoxy-4,6-dimethylphenylboronic acid</strong> (540 mg, 3.0 mmol), tetrakis(triphenylphosphine)palladium (0) (115 mg, 5 mol %) in toluene (12 mL) and sodium carbonate (IM in water, 4 mL) is heated at 95 C. (oil bath temperature) in a pressure tube for 14 hours. The reaction is cooled to room temperature, diluted with ethyl acetate, washed with NaOH (2M) and then brine (2*50 mL). The solvents are dried (sodium sulfate) and removed under reduced pressure. Flash chromatography of the crude product (50% ethyl acetate in hexanes) yields 4-methoxy-2-(6-methoxy-2,4-dimethylphenyl)-6-methylpyrimidin-5-ol as a white solid.
  • 8
  • [ 1067229-17-7 ]
  • [ 355836-08-7 ]
  • [ 1067229-14-4 ]
  • 9
  • [ 1130808-00-2 ]
  • [ 355836-08-7 ]
  • [ 1067228-88-9 ]
  • 10
  • C11H17BO3 [ No CAS ]
  • [ 355836-08-7 ]
  • 11
  • [ 1380434-15-0 ]
  • [ 355836-08-7 ]
  • [ 475171-41-6 ]
  • 12
  • [ 1380434-40-1 ]
  • [ 355836-08-7 ]
  • [ 475171-67-6 ]
  • 13
  • [ 685886-46-8 ]
  • [ 355836-08-7 ]
  • [ 1380434-44-5 ]
  • 14
  • [ 1380434-42-3 ]
  • [ 355836-08-7 ]
  • [ 475171-68-7 ]
  • 15
  • [ 475174-91-5 ]
  • [ 355836-08-7 ]
  • [ 475171-69-8 ]
  • 16
  • 7-bromo-N-(cyclopropylmethyl)-2-ethyl-N-((tetrahydrofuran-3-yl)methyl)pyrazolo[1,5-a]pyridin-3-amine [ No CAS ]
  • [ 355836-08-7 ]
  • [ 475171-70-1 ]
  • 17
  • [ 355836-08-7 ]
  • C27H35N3O3 [ No CAS ]
  • 18
  • [ 355836-08-7 ]
  • [ 475174-92-6 ]
  • 19
  • [ 355836-08-7 ]
  • [ 475171-81-4 ]
  • 20
  • [ 546-67-8 ]
  • [ 355836-08-7 ]
  • (2-methoxy-4,6-dimethylphenyl)lead triacetate [ No CAS ]
  • 21
  • [ 355836-08-7 ]
  • 2’-methoxy-4’,6’-dimethylisoflavanone [ No CAS ]
  • 22
  • [ 355836-08-7 ]
  • [ 1411858-67-7 ]
  • 2’-methoxy-4’,6’-dimethylisoflavanone [ No CAS ]
  • 23
  • [ 615-36-1 ]
  • [ 355836-08-7 ]
  • C15H17NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With palladium diacetate; 2-dicyclohexylphosphino-2',6'-dimethylbiphenyl; In toluene; at 100℃; for 3h; 100ml three-neck eggplant flask fully dried(Condenser, with three-way cock, with magnetic stirrer) 1.30 g (7.2 mmol) of compound 71.03-g (6 mmol) 2-bromoaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.07 g (0.03 mmol) palladium acetate,0.025 g of 2-Dicyclohexylphosphino-2 ', 6'-dimethylbiphenyl(0.06 mmol), 4.15 g (18 mmol) of potassium phosphate monohydrate, and suspended in 18 mL of toluene,The reaction was carried out at 100 C. for 3 hours. Add 10 mL of water to the reaction solution,After extraction with toluene, the organic layer is dried over MgSO4,The solvent was distilled off under reduced pressure to obtain a crude product.Crude product is silica gel column chromatograph(Eluent: hexane / ethyl acetate = 95/5)Compound 48 by purifying with0.390 g (29%, light yellow liquid) was obtained.
  • 24
  • [ 121-43-7 ]
  • [ 874-63-5 ]
  • [ 355836-08-7 ]
YieldReaction ConditionsOperation in experiment
62% Fully dried 300 mL three-neck eggplant flask(With dropping funnel, with three-way cock, with magnetic stirrer)1-methoxy-3,5-dimethylbenzene8.17 g (60 mmol) of Tokyo Chemical Industry Co., Ltd.Add 120 mL of diethyl ether,After cooling to 0 C. in an ice bath, 7.67 g of N, N, N ?, N?-tetramethylethylenediamine (manufactured by Tokyo Chemical Industry Co., Ltd.)(66 mmol) was added, and hexane solution of normal butyl lithium (1.6 mol / L) 39.8 mL (66 mmol)Was added dropwise and reacted for 5 hours.500mL three neck eggplant flaskDiethyl ether (with 3-way cock and magnetic stir bar)After adding 60 mL and 12.47 g (120 mmol) of trimethyl borate (Sigma Aldrich Japan Co., Ltd.)After cooling to -78 C., the reaction solution prepared above is added dropwise,The reaction was allowed to proceed for 18 hours while raising the temperature to room temperature.10 wt% hydrochloric acid water (manufactured by Kanto Chemical Co., Ltd.)After adding 100 mL, after extracting with ethyl acetate 50 mL × 3,Wash the organic layer with pure water 50mL × 2,By drying over MgSO4 and distilling off the solvent under reduced pressure,A crude product was obtained.By recrystallizing the resulting crude product from toluene,Compound 76.67g(62%, white solid) was obtained.
  • 25
  • [ 363-51-9 ]
  • [ 355836-08-7 ]
  • C15H16FNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With palladium diacetate; 2-dicyclohexylphosphino-2',6'-dimethylbiphenyl; In toluene; at 100℃; for 1.5h; 100ml three-neck eggplant flask fully dried1.89 g (10.5 mmol) of Compound 7 (with a condenser, a three-way cock, and a magnetic stirrer)2-Chloro-6-fluoroline1.46 g (10 mmol) (manufactured by Tokyo Chemical Industry Co., Ltd.)0.22 g (0.1 mmol) of palladium acetate,2-Dicyclohexylphosphino-2 ', 6'-dimethylbiphenyl0.082 g (0.2 mmol), potassium phosphate monohydrate6.91 g (30 mmol) was added,Suspend in 18 mL of toluene,The reaction was performed at 100 C. for 1.5 hours.After adding 20 mL of water to this reaction solution and extracting with toluene,The organic layer is dried over MgSO4The solvent was distilled off under reduced pressure to obtain a crude product.The crude product was purified by silica gel column chromatography (eluent;Hexane / ethyl acetate = 95/5)Compound 8 was purified by purification using1.953 g (80%, pale yellow liquid) was obtained.
  • 26
  • [ 355836-08-7 ]
  • C33H36FNO2 [ No CAS ]
  • 27
  • [ 355836-08-7 ]
  • C33H35Cl3FNO2Ti [ No CAS ]
  • 28
  • [ 355836-08-7 ]
  • C33H37NO2 [ No CAS ]
  • 29
  • [ 355836-08-7 ]
  • C33H36Cl3NO2Ti [ No CAS ]
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