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CAS No. : | 374790-93-9 | MDL No. : | MFCD02094008 |
Formula : | C10H15BO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GWEWQKZABZXLJH-UHFFFAOYSA-N |
M.W : | 194.04 | Pubchem ID : | 11356013 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.6 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.18 |
TPSA : | 31.6 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.06 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.01 |
Log Po/w (WLOGP) : | 1.58 |
Log Po/w (MLOGP) : | 0.34 |
Log Po/w (SILICOS-IT) : | 1.25 |
Consensus Log Po/w : | 1.04 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.51 |
Solubility : | 0.603 mg/ml ; 0.00311 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.3 |
Solubility : | 0.971 mg/ml ; 0.00501 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.21 |
Solubility : | 0.119 mg/ml ; 0.000612 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.35 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
78% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2 h; Stage #2: at -78 - 20℃; Stage #3: With methanol In tetrahydrofuran; hexane |
General procedure: n-BuLi in hexane (1.6 M, 65 mL, 0.10 mol) was slowly added toa solution of 2-bromothiophene (11 g, 0.068 mol) in THF (200 mL) at 78 C. After stirring for 2 h at this temperature, the mixturewas added to a solution of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13 g, 0.068 mol) in 150 mL of THF. The mixture was warmed to room temperature and stirred overnight. The reactionwas terminated by adding a small amount of methanol and the resultant solution was washed with water three times. The solution was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: hexane) to give 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)thiophene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With (CyAPDI)CoCH3 In neat (no solvent) at 23℃; for 10 h; | EXAMPLE 9 - Borylation of Aromatic Five-Membered Heterocycle According to the reaction scheme illustrated in Figure 2(a), a scintillation vial (with a magnetic stir bar) was charged with cobalt complex (0.01 mmol) selected from 1-4, 2 methylfuran (1 mmol) and pinacolborane (1 mmol). The reaction was monitored by the analysis of an aliquot of the mixture by GC-FID. The mixture was allowed to stir to completion at room temperature and was quenched by exposure to air. The resulting solid was solubilized in CDC13, 1 ] 3 passed through a plug of silica gel in a Pasteur pipette and then analyzed by H and C NMR spectroscopy without further purification. If desired, the foregoing reaction can also be administered in 2 ml of tetrahydrofuran (THF). Figure 2(a) provides conversion percentages for cobalt complexes 1-4 with values in parenthesis as isolated yields. Further, Figure 2(b) details additional borylation products achieved with Co complexes 2 and 3 according to the foregoing reaction parameters. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; for 16 h; | Example 2 illustrates the sp2-carbon borylation and hydrogenation of a furan substrate to form a corresponding 2-substituted sp3-carbon borylated tetrahydrofuran. Scheme 12 illustrates sp2-carbon borylation of furan with an iridium-based catalyst ([IrOMe(cod)]2 and dtbpy) in hexane (rt for 16 h). The sp2-carbon borylated product is hydrogenated using hydrogen with a rhodium-based catalyst (Rh/Al2O3) in ethanol (rt for 15 h) to form the corresponding hydrogenated, 2-substituted sp3-carbon borylated tetrahydrofuran product. |
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