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CAS No. : | 808140-97-8 | MDL No. : | MFCD16996193 |
Formula : | C9H11BO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZXNZZEIYAXQMJH-UHFFFAOYSA-N |
M.W : | 177.99 | Pubchem ID : | 67394331 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 50.26 |
TPSA : | 49.69 Ų |
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) : | -6.43 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.35 |
Log Po/w (WLOGP) : | -0.16 |
Log Po/w (MLOGP) : | 0.26 |
Log Po/w (SILICOS-IT) : | -0.21 |
Consensus Log Po/w : | 0.25 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.94 |
Solubility : | 2.05 mg/ml ; 0.0115 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.0 |
Solubility : | 1.8 mg/ml ; 0.0101 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.63 |
Solubility : | 4.21 mg/ml ; 0.0237 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.99 |
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 |
---|---|---|
23% | With potassium acetate; bis(pinacol)diborane;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 130.0℃; for 0.75h;Microwave irradiation; | B. S-Cyclopropoxyphenylboronic acidA mixture of i-bromo-3-cyclopropoxybenzene (1.36 mmol, 0.289 g), 4,4,4',4',5,5,5',S'- octamethyl-2,2'-bi(1 ,3,2-dioxaborolane) (2.11 mmol, 0.321 mmol), PdCI2dppf.DCM (0.14 mmol, 0.112 g), KAcO (6.11 mmol, 0.600 g) in a DMSO (3 ml) was heated at 13O0C for 45 minutes, under argon atmosphere in a microwave oven. Ethyl acetate was added and filtered through celite. The organic phase was washed with water and evaporated. The crude mixture was purified by reverse phase using a water/AcN/MeOH system gradient affording 0.090 g (yield 23%) of the expected product.1H NMR (400 MHz, CDCI3) delta ppm: 0.8 (m, 4H), 1.3 (s, 12H), 3.8 (m, 1 H), 7.1 (dd, J=7.6. 2.2 Hz. 1 H). 7.3 (m. 1H). 7.4 (d. J=7.0 Hz1 1H)5 7.5 (d, J=2.0 Hz, 1H)ESI/MS (m/e, %): 260 [(M+1)+, 100] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 130.0℃; for 2.0h;Microwave irradiation; | Example 63; <n="110"/>2-(6-(3-Cyclopropoxyphenyl)-5-methylpyridin-3-ylamino)-5-methylbenzoic acid A. Tert-butyl 2-(6-(3-cyclopropoxyphenyl)-5-methylpyridin-3-ylamino)-5- methylbenzoate A mixture of Intermediate 16 (0.66 mmol, 0.250 g), Intermediate 25 (0.99 mmol, 0.257 g), Pd(PPh3)4 (0.06 mmol, 0.075 g) and K2CO3 (2.32 mmol, 0.320 g) in DMF (7 ml) was heated at 13O0C for 2 hours in a microwave oven. The mixture was filtered through celite and the solvent was evaporated. The crude mixture was purified over a SiO2 eluting with hexane/ethyl acetate mixtures and affording 0.11O g (yield 92%) of the corresponding ester derivative. delta 1H NMR (200 MHz, DMSO-Cf6): 0.74 - 0.79 (m, 2 H), 0.79 - 0.86 (m, 2 H), 1.62 (s, 9 H), 2.30 (s, 3H), 2.35 (s, 3H), 3.57 - 3.90 (m, 1H), 6.97 - 7.24 (m, 4H), 7.27 - 7.49 (m, 3H), 7.68 - 7.81 (m, 1 H)1 8.46 (d, J=2.34 Hz, 1 H), 9.44 (s, 1 H). ESI/MS (m/e, %): 431 [(M+1) 92]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 110.0℃; for 12.0h; | Example 22; <n="90"/>2-(2-(3-Cyclopropoxyphenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acidA. Methyl 2-(2-(3-cyclopropoxyphenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoateIn a schlenck tube, a mixture of Intermediate 17 (0.305 g, 1 mmol) and Intermediate 25 (0.260 g, 1 mmol), 2M K2CO3 (1.98 mmol, 1 ml) and Pd(PPh3J4 (0.1 mmol, 0.114 g) in dioxane (7 ml) was heated at 11O0C for 12 hours, under argon atmosphere. The solvent was evaporated and the crude mixture was extracted between water and ethyl acetate. The organic phase was dried over MgSO4, filtered and the solvent removed. The crude mixture was purified by chromatography over SiO2 eluting with hexane/ethyl acetate mixtures affording 0.205 g (49% of yield) of the expected product. ESI/MS (m/e, %): 402 [(M+1)+, 100]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; chloro(2-dicyclohexylphosphino-2?,6?-dimethoxy-1,1?-biphenyl)(2?-amino-1,1?-biphenyl-2-yl) palladium(II); In tetrahydrofuran; water; at 80.0℃; for 18.0h;Inert atmosphere; | A mixture of 2nd Generation Palladium SPHOS precatalyst (8.39 mg, 0.0 12 mmol), Intermediate 24 (100 mg, 0.233 mmol) and (5-fluoro-2-methoxypyridin-4-yl)boronic acid(59.7 mg, 0.349 mmol) in THF (2 ml) was purged with nitrogen. Then 2M aqueous K3P04 (0.349 ml, 0.699 mmol) was added, and the mixture was purged with nitrogen, capped and heated at 80C for 18 h. Then anhydrous sodium sulfate was added to the mixture, followed by CH2C12 (2 mL). The reaction mixture was decanted and loaded onto a ISCO RediSep 24g silica gel column. The remaining sodium sulfate residue was triturated with 1 mL CH2C12 and the liquid was added to theISCO column. The column was dried with a nitrogen stream and then subjected to gradient elution with 0% to 100% EtOAc in hexanes to give (2S,3R)-methyl 3-cyclopropyl-3-(3-(4-(5-fluoro-2- methoxypyridin-4-yl)phenyl)chroman-6-yl)-2-methylpropanoate.Utilizing a procedure similar to the synthesis of Intermediate 26, (25,3R)-3-(3 -(4-bromophenyl)chroman-6-yl)-3 -cyclopropyl-2-methylpropanoic acid was cross coupled with(3 -cyclopropoxyphenyl)boronic acid to afford (2S ,3R)-3 -(3 -(3 ?-cyclopropoxy- [1,1 ?-biphenyl]-4-yl)chroman-6-yl)-3-cyclopropyl-2-methylpropanoic acid (Example 19). LC/MS: m/e 469 (M+H) |
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