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CAS No. : | 500717-23-7 | MDL No. : | MFCD23135317 |
Formula : | C30H27N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LCSMGMWMTSWXDD-UHFFFAOYSA-N |
M.W : | 401.54 | Pubchem ID : | 59254080 |
Synonyms : |
|
Num. heavy atoms : | 31 |
Num. arom. heavy atoms : | 24 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 131.87 |
TPSA : | 12.03 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) : | -2.74 cm/s |
Log Po/w (iLOGP) : | 4.18 |
Log Po/w (XLOGP3) : | 8.46 |
Log Po/w (WLOGP) : | 8.04 |
Log Po/w (MLOGP) : | 6.55 |
Log Po/w (SILICOS-IT) : | 7.9 |
Consensus Log Po/w : | 7.02 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -8.1 |
Solubility : | 0.00000319 mg/ml ; 0.0000000079 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -8.58 |
Solubility : | 0.00000105 mg/ml ; 0.0000000026 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -11.99 |
Solubility : | 0.0000000004 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.41 |
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 |
---|---|---|
95% | Stage #1: With trifluoroacetic acid In tetrahydrofuran at 20℃; for 0.166667 h; Stage #2: With sodium hydroxide In tetrahydrofuran; dichloromethane; water |
Bis(9,9-dimethyl-9H-fluoren-7-yl)amine (B) 0.4 g of tert-Butoxycarbonyl-protected arylamine 1 (0.8 mmol) was dissolved in 1 ml of tetrahydrofurane, and 8 ml of trifluoroacetic acid (TFA) was added to the resulting mixture. Then, the reaction mixture was stirred at room temperature for 10 minutes, thereby obtaining a solution having a color that turned dark green. TFA was evaporated in a vacuum, dichloromethane was added to the resultant, and the resultant was neutralized using an aqueous saturated sodium hydroxide solution. The mixture was extracted with solid dichloromethane solutions as described above, and the remaining moisture in the organic layer was removed. Then, column chromatography (stationary phase: silica gel, mobile phase: ethyl acetate:hexane=1:10 volume ratio) was performed on the resultant solution to obtain 0.3 g of pale yellow Compound 2 at a yield of 95percent. Mp: 178 °C 1H NMR (300 MHz, (CD3)2CO):δ 7.7-7.67 (m, 4H), 7.48 (d, J=6.9 Hz), 7.36 (s, 2H), 7.31-7.22 (m, 4H), 7.18 (d, 2H J=7.2 Hz), 1.46 (s, 12H). 13C NMR(300MHz,(CD3)2CO):δ 155.97, 153.83, 144.45, 140.29, 132.48, 127.79, 126.73, 123.27, 121.67, 119.69, 117.32, 112.46, 47.28, 27.53. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 85℃; for 3 h; | 6.27 g (30 mmol) of 2-amino-9,9'-dimethylfluorene, 5.46 g (20.0 mmol) of 2-bromo-9,9'-dimethylfluorene, 366 mg (0.4 mmol) of Pd2(bda)3 where dba is dibenzylideneacetone, 80 mg (0.4 mmol) of PtBu3, and 2.88 g (30 mmol) of NaOtBu were dissolved in 60 mL of toluene, and the mixture was refluxed at 85°C for 3 hours. The mixture was cooled to room temperature and subjected to extraction three times with 50 mL of water and 50 mL of diethyl ether. An organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separately purified using silica gel column chromatography to obtain 6.50 g of Intermediate I-1 (Yield: 81 percent) The produced compound was identified using 1H NMR and MS/FAB. C30H27N:calc. 401.21, found 402.231H NMR (400MHz, CDCl3). δ7.78 (dd, 2H), 7.56 (d, 2H), 7.36-7.30 (m, 2H), 7.14-7.09 (m, 2H), 7.02 (d, 2H), 6.94 (d, 2H), 5.85 (s, 1H), 1.65 (s, 12H) |
61% | With sodium t-butanolate In toluene at 90℃; for 3 h; Inert atmosphere | Synthesis Example 7: Synthesis of Compound 65; Synthesis of Intermediate 13 [Show Image] Under a nitrogen atmosphere, 1.91 g (7.0mmol) of 9,9'-dimethyl-2-bromofluorene, 2.2 g (10.5 mmol) of 9,9'-dimethyl-2-aminofluorene, 2.0 g (21 mmol) of t-BuONa, 130 mg (0.14mmol) of Pd2(dba)3, and 28 g (0.14mmol) of P(t-Bu)3 were dissolved in 30 ml of toluene, and then the mixture was stirred at 90°C for 3 hours. After the reaction was completed, the reaction product was cooled to room temperature and extracted three times with distilled water and 50 ml of diethylether. The organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified using silica gel column chromatography to obtain 1.7 g (yield: 61 percent) of Intermediate 13. This compound was identified using HR-MS. C30H27N calc.: 401.2143; found 401.2147. |