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CAS No. : | 1035690-24-4 | MDL No. : | MFCD16994464 |
Formula : | C15H21BO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QRRJFVBHNJSHKB-UHFFFAOYSA-N |
M.W : | 260.14 | Pubchem ID : | 57467635 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.6 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 76.91 |
TPSA : | 27.69 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.45 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.43 |
Log Po/w (WLOGP) : | 2.46 |
Log Po/w (MLOGP) : | 1.92 |
Log Po/w (SILICOS-IT) : | 2.36 |
Consensus Log Po/w : | 2.04 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.65 |
Solubility : | 0.0583 mg/ml ; 0.000224 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.69 |
Solubility : | 0.0529 mg/ml ; 0.000203 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.34 |
Solubility : | 0.0119 mg/ml ; 0.0000458 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.15 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 100℃; for 3h; | INTERMEDIATE 37 2-(3-cyclopropoxyphenyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane; A mixture of intermediate 36 (2.87g, 10.9mmol), bis(pinacolato)diboron (4.16g, 16.4mmol) and potassium acetate (3.2g, 32.7mmol) in anhydrous dioxane, was stirred under nitrogen atmosphere and then PdCl2dppf.CH2CI2 (0.5g, 0.55mmol) was added. The reaction mixture was heated at 1000C for 3h. The crude was then filtered over celite, washed with dioxane and evaporated under reduce pressure. The residue obtained was purified by reverse-phase chromatography eluting with a gradient of water and AcN/MeOH (1/1 ) (from 0% to 100% of AcN/MeOH(1/1 )). The desired product was obtained as a yellow oil. Yield=55%. LRMS: m/z 261 (M+1 )+. Retention time: 7.23 min |
41% | With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 100℃; for 21h;Inert atmosphere; | 2-(3-(Cyclopropyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2- dioxaborolane (T24.2). A stirred mixture of T24.1 (0.144 g, 0.676 mmol), bis(pinacolato)diboron (0.189 g, 0.745 mmol), potassium acetate (0.2007 g, 2.04 mmol), and dichloro[l ,r-bis(diphenylphosphino)ferrocene]palladium (II) DCM adduct (25.3 mg, 0.0346 mmol) in dry 1,4-dioxane (3.0 mL) was purged three times with argon and placed under vacuum three times. The mixture was heated to 100C, and monitored with LC-MS and TLC. After 21 hours, the reaction was cooled to room temperature and filtered through Celite filter aid. The organic solvent was removed under reduced pressure. The residue was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford T24.2 as a colorless oil (72 mg, 41% yield). 1H NMR (400 MHz, CDCl3) delta ppm 7.51 (1 H, d, J=2.7 Hz), 7.44 (1 H, d, J=7.0 Hz), 7.34 (1 H, m), 7.14 (1 H, dd, J=7.6, 2.2 Hz), 3.80 (1 H, ddd, J=8.8, 5.9, 3.3 Hz), 1.36 (12 H, s), 0.82 (4 H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 23 - 90℃; for 19h;Inert atmosphere; | Methyl 3'-(cyclopropyloxy)-2-(2,2-dimethylcyclopentyI)-l,l'- biphenyl-4-carboxylate (T24.3). To a stirred solution of T7.6F (438.2 mg, 1.15 mmol) in dry DMF (5.0 mL) at 23C was added potassium carbonate (480.3 mg, 3.47 mmol) followed by tetrakis(triphenylphosphine)palladium (140.2 mg, 0.121 mmol). The mixture was purged three times with argon and placed under vacuum three times. Before heating, T24.2 ( 523.1 mg, 2.01 mmol) was added via syringe and then the mixture was heated to 90C. After 19 hours, LCMS showed reaction was complete. The mixture was cooled to room temperature and then diluted with water. After extracting three times with EtOAc, the mixture was concentrated in vacuo and then purified on silica gel (0%-10% EtOAc/hexane) to afford T24.3 as a colorless oil that was used without further purification (411.5 mg, 98% yield). MS ESI (pos.) m/e: 365.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; at 70 - 100℃;Inert atmosphere; | General procedure: General Procedure D: Preparation of Coupled Aryl and Heteroaryl Groups Using Suzuki Catalyzed Coupling Conditions Between an Organoboronic Acid or Ester and an Aryl Halide or Heteroaryl Halide (0329) [00218] A suspension of heteroaryl chloride (1 equivalent), organoboronic acid or organoboronic ester (1.2 equivalents), K3PO4 (3.0 equivalents) and Pd(dppf)Cl2?DCM (5 mol%) or Pd2(dba)3 (10 mol%) in DME or 1,4-dioxane (40 mL/mmol) was stirred at 70-100 oC for 2-6 hours under N2. Then, the reaction mixture was quenched with water (30 mL/mmol) and resulting mixture extracted with EtOAc (30 mL/mmol x 3). The organic phases were washed with water (30 mL/mmol) and brine (30 mL/mmol), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the resulting residue was purified by silica gel column chromatography to afford the coupled ring system. | |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 16h; | General procedure: A mixture of Compound 27B (1.35 g, 5.4mmol), Pd(dppf)C12 (0.35 g, 0.43 mmol), 4,4,4,4,5,5,5?, 5?-octamethyl-2,2?-bi( 1,3 ,2-dioxaborolane) (2.09 g, 8.22 mmol), and potassium acetate (1.62 g, 16.5 mmol) in 1,4-dioxane (50 ml) was heated at 80C for 16 hours. The mixture was diluted with water (200 mL) and extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water (200 mL) and brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 10% v/v) to furnish Compound 27C. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.78% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; at 70℃; for 3h;Inert atmosphere; | General procedure: According to scheme 2, step viii: A mixture of intermediate 15a (200.00 mg, 518.07 umol, 1.00 eq), (2-methoxyphenyl)-boronic acid (157.45 mg, 1.04 mmol, 2.00 eq), Pd(PPh3)4 (119.73 mg, 103.61 umol, 0.20 eq), Na2CO3 (2 M, 1.17 mL, 4.50 eq) in THF (4.00 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 70C for 3 hours under N2 atmosphere. The mixture was added water(20mL), extracted with AcOEt (20mLx3), the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (PE:EA=0:1) to give intermediate 16a (190.00 mg, crude) as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; at 70℃; for 3h;Inert atmosphere; | General procedure: According to scheme 2, step viii: A mixture of intermediate 15a (200.00 mg, 518.07 umol, 1.00 eq), (2-methoxyphenyl)-boronic acid (157.45 mg, 1.04 mmol, 2.00 eq), Pd(PPh3)4 (119.73 mg, 103.61 umol, 0.20 eq), Na2CO3 (2 M, 1.17 mL, 4.50 eq) in THF (4.00 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 70C for 3 hours under N2 atmosphere. The mixture was added water(20mL), extracted with AcOEt (20mLx3), the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (PE:EA=0:1) to give intermediate 16a (190.00 mg, crude) as a yellow oil. |
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