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CAS No. : | 58775-05-6 | MDL No. : | MFCD03093998 |
Formula : | C21H26 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DFZYPLLGAQIQTD-UHFFFAOYSA-N |
M.W : | 278.43 | Pubchem ID : | 4090082 |
Synonyms : |
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.43 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 93.43 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -3.11 cm/s |
Log Po/w (iLOGP) : | 3.94 |
Log Po/w (XLOGP3) : | 6.89 |
Log Po/w (WLOGP) : | 5.85 |
Log Po/w (MLOGP) : | 6.6 |
Log Po/w (SILICOS-IT) : | 6.54 |
Consensus Log Po/w : | 5.97 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -6.2 |
Solubility : | 0.000177 mg/ml ; 0.000000634 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -6.7 |
Solubility : | 0.0000554 mg/ml ; 0.000000199 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -7.6 |
Solubility : | 0.00000693 mg/ml ; 0.0000000249 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.93 |
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 |
---|---|---|
With aluminum (III) chloride; In 1,2-dichloro-ethane; at 10 - 15℃; for 0.75h; | the 6.0g (36.0mmol) fluorene was dissolved in 25ml dichloroethane, was added 10g (75mmol) of aluminum chloride, the temperature controlled at 10-15 deg.] C, was added dropwise t-butyl chloride 7.0g (76mmol), dropwise with time 15min, the reaction mixture was reacted at 10-15 deg.] C 30min, the reaction system was slowly poured into 100g of crushed ice, the layers were separated and the aqueous phase was extracted with 50ml of dichloroethane, the combined The organic phase was dried over anhydrous sodium sulfate, and the solvent removed in vacuo to give 2,7-di-tert-butyl-fluorene 9.6 g of crude product, a yield of more than 100%, GC purity 99.29%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With picoline; tert.-butylhydroperoxide; chlorophyllin coppered trisodium salt; In water; acetone; at 80℃; for 10h; | General procedure: A solution of secondary alcohol (or diarylmethane) (0.5 mmol), SCC (1 mol %), 70% TBHP(1.5 mmol), and 4-methylpyridine (1.5 mmol) in acetone/H2O (1:0.5 mL) was stirred at 80C for 10 h.The reaction mixture was quenched with the saturated solution of sodium thiosulfate (5 mL) andextracted with dichloromethane (3 10 mL). The combined dichloromethane extracts were dried overanhydrous Na2SO4, filtrated, and then the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE/EtOAc as the eluent to obtain the desired products. |
With cobalt(II) nitrate hexahydrate; In water; at 80℃; for 10h; | A method for preparing an anthrone compound having the following structural formula:The substrate 2,7-di-tert-butylfluorene 278 mg (1 mmol) was added to a 50 mL Shrek tube, and the amount of cobalt nitrate hexahydrate was added. The amount of cobalt nitrate hexahydrate added was the molar amount of Co. 0.5%, specifically 0.15 mg, the molar amount of ligand L1 is 0.5% of the molar amount of the substrate, specifically 0.2 mg, and potassium phosphate 1.69 g (7 eq.) and water 3 mL are added.The magnet was added, and the reaction was stirred for 10 hours in an oil bath at 80 C under air conditions. After the reaction was completed, the reaction solution was separated by filtration to obtain 284 mg of the desired product, yield 97%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.6% | With bromine;iron; In tetrachloromethane; | 4-Bromo-2,7-di-t-butylfluorene was then synthesised according to Scheme 3. Specifically, to a mixture of 2,7-di-t-butylfluorene (5.95 g, 21.4 mmol) and catalytic amount of iron powder in CCl4 (40 ml) was added a solution of bromine (3.9 g, 24.3 mmol) in CCl4 (10 ml) at 0 C. The reaction mixture was stirred for more than 3 h at room temperature and then was quenched with water. The mixture was extracted with ether, and the ether solution was washed with 10% NaOH solution, dried over MgSO4, and evaporated under vacuum to afford the residue which was recrystallized from hot ethanol to give 4-bromo-2,7-di-t-butylfluorene (6.7 g, 87.6%). 1H NMR (CDCl3): delta 8.44 (d, 1H, J=8.4, H5), 7.6-7.4 (m, 4H, H1, H3, H6 and H8), 3.89 (s, 2H, H9), 1.38, 1.36 (each s, 9H, t-Bu). |
87.6% | With bromine;iron; In tetrachloromethane; at 0 - 20℃; for 3h; | To a mixture of 2,7-di-t-butylfluorene (5.95 g, 21.4 mmol) and catalytic amount of iron powder in CCl4 (40 ml) was added a solution of bromine (3.9 g, 24.3 mmol) in CCl4 (10 ml) at 0 C. The reaction mixture was stirred for more than 3 hours at room temperature and then was quenched with water. The mixture was extracted with ether, and the ether solution was washed with 10% NaOH solution, dried over MgSO4, and evaporated under vacuum to afford the residue which was recrystallized from hot ethanol to give 4-bromo-2,7-di-t-butylfluorene (6.7 g, 87.6%). 1H NMR (CDCl3): delta 8.44 (d, 1H, J=8.4, H5), 7.6-7.4 (m, 4H, H1, H3, H6 and H8), 3.89 (s, 2H, H9), 1.38, 1.36 (each s, 9H, t-Bu). |
80% | With 1,2-propylene cyclic carbonate; N-Bromosuccinimide; at 80℃; for 2h; | 11.4 g (40.9 mmol) of 2,7-di-tert-butylfluorene, 8.45 g (47.5 mmol) of N-bromosuccinimide and 80 mL of propylene carbonate were charged in a 500 mL reactor thoroughly dried and purged with argon , And stirring was continued for 2 hours in an oil bath at 80 C. The reaction solution was cooled to room temperature and diluted with diethyl ether. The obtained fraction was washed three times with water in a separatory funnel, then washed with saturated brine and dried over anhydrous magnesium sulfate. After filtration of the magnesium sulfate, the filtrate was distilled off, and the residue obtained was recrystallized from ethanol to obtain the target compound (hereinafter, referred to as the compound (1)) represented by the following formula (1)) Was obtained in an amount of 11.7 g (yield 80%). |
With trimethylbenzylammonium bromide; In methanol; dichloromethane; at 25℃; for 3h; | A mixture of 9g (34mmol) 2,7- di-tert-butyl fluorene was dissolved in 40ml methanol was heated to 25 , was added dropwise 12.6g (32mmol) of benzyl a mixture of trimethyl ammonium tribromide and 200ml of methylene chloride solution, 2.0hrs addition was completed, the reaction was kept 1.0hrs, the reaction was quenched with water, washed three times to neutral, each 50ml of water, the organic phase sulfuric anhydride sodium sulfate, and removing the solvent to give 2,7-di-t-butyl-4-bromo-fluorenyl crude 12.3g, GC purity 99.73%, 0.19% dibromide, toluene and recrystallized twice from ethanol, the GC purity 99.97%, 0.0067 dibromide %, yield 90%. | |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; at 15℃; for 3h; | 139.2g (0.5mol) of 2,7-di-tert-butylfluorene was dissolved in 2L of propylene carbonate solvent in a 5L three-necked flask with mechanical stirring, thermometer and heating reaction device. The reaction temperature was controlled at 15 C. 74.3 g (0.26 mol) of dibromohydantoin was added, and the mixture was continuously stirred under constant temperature for 3 hours, and the reaction was terminated by high performance liquid chromatography, and the reaction was terminated by adding water. Saturated liquid The organic layer was washed with an aqueous sodium hydrogen sulfate solution and dried over anhydrous magnesium sulfate. The obtained product was dispersed in benzene, and 18.7 g (0.14 mol) of aluminum trichloride catalyst was added thereto, and the mixture was stirred at a reaction temperature of 5 C for 8 hours, and the reaction was terminated by high performance liquid chromatography. The reaction was terminated by adding water, and the reaction liquid was saturated. After washing with an aqueous solution of sodium hydrogensulfate, the organic layer was separated, dried over anhydrous magnesium sulfate, and then recrystallized from toluene-methanol mixed solvent to give the product 4-bromo-9-phenylfluorene as 144.5 g. 4-Bromo-9-phenylfluorene was dispersed in 2 L of dimethyl sulfoxide solvent, the reaction temperature was controlled at 5 C, 83.7 g (0.59 mol) of methyl iodide was added, mechanical stirring was carried out, liquid phase was followed, and the reaction was finished with water, and separated. The organic layer was purified by distillation to obtain 142.7 g of 4-bromo-9-methyl-9'-phenylfluorene as an off-white powder. The total yield of the reaction was 85.2%, the content was 99.5% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.5% | (ii) Synthesis of (2,7-di-tert-butylfluorenyl) cyclopentadienyl di-p-tolyl methane A 300 ml two-necked flask equipped with a magnetic stirrer, a three-way cock and a dropping funnel, was purged thoroughly with nitrogen. 2,7-di-tert-butylfluorene 1.58 g (5.66 mmol) was placed in the flask, and dehydrated tetrahydrofuran 40 ml was further added. With cooling in an ice bath, 1.56 mol/L n-hexane solution of n-butyllithium, 3.8 ml (5.9 mmol), was dropwise added. The contents were stirred at room temperature in a nitrogen atmosphere for 6.5 hours to obtain a solution. With the flask cooled in a dry ice/methanol bath, a solution of 6,6-di-p-tolyl fulvene 1.76 g (6.82 mmol) in 20 ml of dehydrated tetrahydrofuran, was dropwise added to the flask over a period of 20 minutes by means of the dropping funnel. The liquid temperature was gradually raised to room temperature, and the contents were stirred in a nitrogen atmosphere at the temperature for 18 hours to obtain a solution. A saturated aqueous solution of ammonium chloride 100 ml and diethyl ether 100 ml were gradually added in this order. The resulting two-phase solution was poured into a 300 ml separation funnel, and the funnel was shaken several times so that the water phase was removed. The obtained organic phase was washed three times with water 100 ml and once with a saturated salt solution 100 ml, and dried over anhydrous magnesium sulfate. The solution was filtered to remove solids, and the solvent of the filtrate was distilled away. The resultant solid was washed with n-hexane to obtain 2.05 g of (2,7-di-tert-butylfluorenyl)cyclopentadienyl di-p-tolyl methane as a white solid (3.82 mmol, 67.5% yield). Identification of the (2,7-di-tert-butylfluorenyl) cyclopentadienyl di-p-tolyl methane was made by 1H NMR and the FD-mass spectrometric analysis, the results being given below: 1H NMR spectrum (270 MHz, CDCl3): delta/ppm 1.11 (s, t-Bu, 18H), 2.23 (s, Me, 6H), 2.8-3.0 (br, CH2(Cp), 1H), 5.37 (s, CH(9-Flu), 1H), 6.0-6.4 (br, Cp, 4H), 6.8-7.0 (br, Ar(Flu) and Ar(p-tol), 6H), 7.0-7.3 (br, Ar(p-tol), 4H), 7.16 (dd, J=8.1 Hz, J=1.3 Hz, Ar(Flu), 2H), 7.34 (d, J=8.1 Hz, Ar(Flu), 2H) FD-MS spectrum: M/z 536 (M+) |
Tags: 58775-05-6 synthesis path| 58775-05-6 SDS| 58775-05-6 COA| 58775-05-6 purity| 58775-05-6 application| 58775-05-6 NMR| 58775-05-6 COA| 58775-05-6 structure
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