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CAS No. : | 325129-69-9 | MDL No. : | MFCD08704230 |
Formula : | C27H36B2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RVFLMSKITNJVRB-UHFFFAOYSA-N |
M.W : | 446.19 | Pubchem ID : | 20640927 |
Synonyms : |
|
Num. heavy atoms : | 33 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.56 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 137.34 |
TPSA : | 36.92 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -4.48 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 6.39 |
Log Po/w (WLOGP) : | 4.59 |
Log Po/w (MLOGP) : | 3.22 |
Log Po/w (SILICOS-IT) : | 4.47 |
Consensus Log Po/w : | 3.73 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -6.77 |
Solubility : | 0.0000759 mg/ml ; 0.00000017 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -6.96 |
Solubility : | 0.0000492 mg/ml ; 0.00000011 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -9.03 |
Solubility : | 0.00000042 mg/ml ; 0.0000000009 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.44 |
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 |
---|---|---|
83% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane for 4 h; Inert atmosphere; Heating | 2,7-dibromo-9,9-dimethyl-9H-fluorene (130g, 369 mmol), bis(pinacolato)diborane (225g, 886 mmol) and potassium acetate (217g, 2.22 mol) was suspended in 1.4L of dioxane. The solution was degassed and saturated with argon. Then added PdCl2(dppf)CH2Cl2 (15g, 18 mmol). The reaction mixture was heated to boiling for 4 hours under a protective gas atmosphere. The mixture was filtered and washed with dioxane.After the crude product was filtered, the use of THF in a Soxhlet extractor for the remaining residue was extracted, then filtered. Produce 137g (83percent of theory) of a gray solid. Purity> 95percent (NMR performed in CDCl3). The following compounds were prepared analogously: |
78% | at 90℃; for 48 h; Inert atmosphere | Under nitrogen protection,Intermediate 2-1 (3.52 g, 10 mmol), diboronic acid pinacol (7.62 g, 30 mmol), K2CO3 solution (16 mL, 2 mol/L), Pd(PPh3)4 (0.21 g, 0.18 mmol) were added to the reactor. The reaction was carried out at 90 ° C for 48 h, and purified to give Intermediate 2-2 (3.48 g, 78percent). |
61% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane for 9 h; Reflux | Preparation Example 13] Preparation of Compound M[241] [242] 2.7-dibromo-9,9-dimethyl-9H-fluorene (25g, 71.0mmol), bis(pinacolato)diboron, (37.87g, 149mmol), 1,4-dioxane (300mL), 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.58g, 0.7mmol), and potassium acetate (13.94g, 142mmol) were mixed and stirred under reflux. After 9 hours, the reactant was cooled to room temperature, and an organic layer was extracted by adding saturated sodium chloride aqueous solution and ethylacetate, dried over magnesium sulfate, and then treated with activated charcoal, followed by filtering with celite. A solid prepared by concentrating the filtrate under reduced pressure was re-crystallized in ethylacetate, thereby obtaining Compound M (30.9g, 61percent).[243] 1H NMR (CDCl3) d 7.80 (m, 2H), 7.60 (m, 2H), 7.40 (m, 2H), 1.67-0.86 (s, 6H), 1.26 (s, 24H) |
47% | With potassium acetate In dimethyl sulfoxide at 80℃; for 9 h; | Under an argon atmosphere, Intermediate 4-1. (2.0 g, 5.8 mmol), bis (pinacolatodiboron) (4.4 g, 17. mmol), a palladium (II) chloride diphenylphosphinoferrocenium*methylene chloride complex (1:1) (0.14 g, 0.2 mmol), potassium acetate (3.4 g, 35 mmol) and dimethyl sulfoxide (40 mL) were added to a 200-mL three-necked flask, and the whole was stirred at 80°C for 9 hours. Water (100 mL) was added to the reaction liquid in such a manner that a solid would be precipitated. Then, the solid was dried under reduced pressure. The solid was purified by means of silica gel column chromatography, whereby Intermediate 4-2 was obtained (amount 1.2 g, yield 47 percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; Stage #2: at 20℃; for 2 h; |
9,9-dimethyl-9H-2,7-dipinacolborylfluorene: the solution of 9,9-dimethyl-9H-2,7-dibromofluorene (17.6g, 50mmol) in anhydrous THF(100mL) was stirred and cooled to 78 °C, to which the n-Butyllithium(2.5M,44mL)was added over a period of 30 min.T wo hour slater isopropoxyboronicacid pinacol ester (25.5 mL)was add edand the mixture was still stirred at room temperature for two hours. After the addition of NH4Cl (20percent,20 mL), tesolvents were removed and the residue was extracted by dichloromethane.The solvent was removed ina vacuum and the crude product was pure enough .Yield:90percent. 1H NMR(CDCl3) δ 1.38(s,24H),1.52(s,6H),7.76(d,2H),7.82(q,2H), 7.89(s,2H)(Fig. S2). |
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