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CAS No. : | 144981-85-1 | MDL No. : | MFCD12024272 |
Formula : | C15H13I | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DVLSJPCXPNKPRJ-UHFFFAOYSA-N |
M.W : | 320.17 | Pubchem ID : | 11023630 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 77.1 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.65 cm/s |
Log Po/w (iLOGP) : | 3.04 |
Log Po/w (XLOGP3) : | 5.07 |
Log Po/w (WLOGP) : | 4.6 |
Log Po/w (MLOGP) : | 5.04 |
Log Po/w (SILICOS-IT) : | 5.45 |
Consensus Log Po/w : | 4.64 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.57 |
Solubility : | 0.000854 mg/ml ; 0.00000267 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.81 |
Solubility : | 0.00493 mg/ml ; 0.0000154 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.88 |
Solubility : | 0.0000424 mg/ml ; 0.000000132 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.62 |
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 |
---|---|---|
91% | Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 0.166667 h; Stage #2: at 0 - 20℃; |
2-Iodofluorene (3 g; 10.27 mmol, 1 equiv) was dissolved in 50 mL of anhydrous tetrahydrofuran. Thesolution was cooled to 0°C and 2.6 g of potassium tert-butoxide (23.16 mmol, 3equiv) was added. During the process, the transparent solution became red.After the solution had been stirred for 10 min, 1.44 g of iodomethane(23.16 mmol, 3 equiv) was added, turning the red solution milky. The solution wasreturned to room temperature and stirred for another 12 hours. After 100 mLdeionized water was added, the solution was extracted with ethyl acetate (100mL X 3). The combined organic solution was then dried over magnesium sulfate,and filtered off. The filtrate was condensed under vacuum to obtain a viscousliquid. Further purification by column chromatography (all n-hexane) on silicagel afforded 3.0 g of product 1 in a yield of 91percent. 1H NMR (300 MHz,CDCl3, δ) 1.47(s, 6H), 7.34-7.36(m, 2H), 7.40-7.45(m, 1H) 7.48(s,1H), 7.64-70(m, 2H), 7.75-7.76(m, 1H) |
90% | Stage #1: With sodium hydroxide; benzyltrimethylammonium chloride In water; dimethyl sulfoxide at 20℃; for 3 h; Stage #2: at 20℃; for 3 h; |
[Step 1] Synthesis of 2-iodo-9,9-dimethylfluorene A synthesis method of 2-iodo-9,9-dimethylfluorene is described. A synthesis scheme of 2-iodo-9,9-dimethylfluorene is shown in (D-1). 25 g (86 mmol) of 2-iodofluorene and 1.5 L of dimethylsulfoxide (abbreviation: DMSO) were put into a 2.0 L three-neck flask, and 1.0 g (5.4 mmol) of benzyltrimethylammonium chloride and 24 mL of 50percent sodium hydroxide aqueous solution were added to the mixture. This mixture was stirred at room temperature for 3 hours. Thereafter, 19 g (130 mmol) of iodomethane was added to this reaction mixture and stirred at room temperature for 3 hours. After completion of the reaction, the reaction solution was washed with 1.0 mol/L hydrochloric acid, a water layer was extracted with ethyl acetate, combined with an organic layer and washed with saturated saline, and then dried with magnesium sulfate. After drying, the mixture was subjected to suction filtration, and a filtrate was concentrated. An obtained residue was purified by silica gel column chromatography (developing solvent: hexane), and an obtained solution was concentrated. When an obtained solid was recrystallized with a mixed solvent of chloroform and hexane, 24.7 g of a white, powdery solid of 2-iodo-9,9-dimethylfluorene, which was a target matter, was obtained with the yield of 90percent. |
70% | Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 1.5 h; Stage #2: for 2 h; |
2-2: Synthesis of 9,9-dimethyl-2-iodofluorene: Potassium tert-butoxide (21.8 g, 0.19 mol) was added to cooled anhydrous tetrahydrofuran, in which 2-iodofluorene(25.0 g, 85.6 mmol) was dissolved, and then stirred at room temperature for 1.5 hours to prepare a first mixedsolution. Subsequently, methyl iodide (28.2 g, 0.19 mol) was added to the first mixed solution to prepare a second mixedsolution, and then the second mixed solution was stirred for 2 hours to obtain potassium iodide. Subsequently, theobtained potassium iodide was filtered, a solvent was removed under reduced pressure, and a reaction product wasseparated by silica column chromatography (hexane). The yield of the reaction product was 70percent.1H NMR(300 MHz, CDCl3) δ(TMS, ppm): 1.47(6H, s, -CH3), 7.31(2H, m, Ar-H)), 7.45(2H, m, Ar-H), 7.66(1H, d, Ar-H),7.73(1H, d, Ar-H), 7.85(1H, s, Ar-H) |
64% | Stage #1: With benzyltrimethylammonium chloride; sodium hydroxide In water; dimethyl sulfoxide at 20℃; for 3 h; Stage #2: at 20℃; for 3 h; |
1 g (3.44mmol) of 2-iodofluorene and 100 mL of dimethylsulfoxidewere put into a 500 mL three-neck round-bottom flask.Subsequently, 0.04 g (0.22 mmol) of benzyltrimethylammonium chloride and 1 mL of 50percent sodium hydroxide aqueous solution were added to the mixture. This mixture was stirred at RT for 3 h. Thereafter, 0.76 g (5.2 mmol) of iodomethane was added into the reaction mixture, which was stirred at RT for an additional 3 h. After completion of the reaction, the reaction solution was washed with 1.0 mol/L hydrochloric acid; a water layer was extracted three times with ethyl acetate. The collected organic layer was washed with saturated saline, and then dried with magnesium sulfate.After drying, the mixture was subjected to suction filtration,and the filtrate was concentrated. An obtained residue was purified by silica gel column chromatography (hexane aseluent), and an obtained solution was concentrated. The residue solid was recrystallized with a mixed solvent of chloroform and hexane to yield 0.7 g of a white, powdery solid of 2-iodo-9,9-dimethylfluorene (64percent yield) (the chemical structure in Scheme 2).1H NMR (CDCl3, 400MHz) δH7.92 (s, 1H), 7.70 (d, J= 8.4 Hz, 1H), 7.66 (d, J =8.4 Hz 1H), 7.60 (d, J= 8.4 Hz, 1H), 7.47 (d, J= 8.4 Hz,1H), 1.37 (s, 6H), MS (GC-mass): m/z320.0 [M+]; C15H13I(320.1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; for 8 h; Inert atmosphere | 2-iodo-9,9'-dimethylfluorene (3.2 g, 10 mmol), bis(pinacolato)diboron (2.79 g, 11 mmol, potassium acetate (2.94 g, 30 mmol), DMF (80 mL) was added to a mixture of Pd(dppf)Cl2(360 mg, 0.5mmol). Under argon protection system, 90°C reactor 8 h. The reaction was stopped, the mixture was cooled to room temperature and poured into 200 mL of water, extracted with ethyl acetate (50 mL × 3), then with saturated brine several times, the combined organic phases were dried over anhydrous magnesium sulfate.Rotary evaporation under reduced pressure, the solvent was removed, the residue with petroleum ether: ethyl acetate = 20: 1 (v / v )as eluant separated by column chromatography on silica gel (200-300 mesh) to give a white solid 2.82 g, yield 88percent |
80% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 100℃; for 6 h; Inert atmosphere | A three-necked flask was charged with 2-iodo-9,9-dimethylfluorene (2g, 6.3mmol), bis (pinacolato) diboron (1.9g, 7.5mmol), potassium acetate (2.9g, 30mmol), Pd (dppf) Cl2 (150mg , 0.21 mmol) and 80mL DMF, under the protection of argon, the mixture was heated to 100oC reaction 6h, cooled to room temperature, extracted with ethyl acetate, washed with saturated brine 3 times, the organic layer was dried over anhydrous sodium sulfate, and removed by rotary evaporation the solvent, the residue was purified by silica gel column chromatography, to V (petroleum ether): V (ethyl acetate) = 10: 1 as eluant to give a white solid was purified 1.6g, 80percent yield. |