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CAS No. : | 1308652-64-3 | MDL No. : | MFCD22200534 |
Formula : | C30H34NP | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DGWSERVYJXYEDY-UHFFFAOYSA-N |
M.W : | 439.57 g/mol | Pubchem ID : | 53359212 |
Synonyms : |
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Num. heavy atoms : | 32 |
Num. arom. heavy atoms : | 19 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 142.9 |
TPSA : | 18.52 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -3.17 cm/s |
Log Po/w (iLOGP) : | 4.68 |
Log Po/w (XLOGP3) : | 8.19 |
Log Po/w (WLOGP) : | 8.56 |
Log Po/w (MLOGP) : | 6.92 |
Log Po/w (SILICOS-IT) : | 7.69 |
Consensus Log Po/w : | 7.21 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -7.9 |
Solubility : | 0.00000553 mg/ml ; 0.0000000126 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -8.44 |
Solubility : | 0.0000016 mg/ml ; 0.0000000036 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -9.52 |
Solubility : | 0.000000133 mg/ml ; 0.0000000003 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.4 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338-P273-P501 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335-H413 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
88.3% | (Setting-Up and Reaction) To a 200 mL four-necked round-bottomed flask, a three-way stopcock, a Teflon-coated magnetic stirring bar, a 20 mL dropping funnel, and a thermometer were attached, and the inside was purged with nitrogen. To this flask, <strong>[902518-11-0]N-(2-bromophenyl)carbazole</strong> (7) (8.8 g, 27.3 mmol, 1.0 eq.) obtained in the first step and anhydrous tetrahydrofuran (hereinafter, abbreviated as THF) (54.6 mL) were sequentially added, and the obtained reactant solution was cooled to -70C by use of a dry ice/acetone bath. Subsequently, a n-butyllithium (hereinafter, abbreviated as n-BuLi)/n-hexane solution (1.60 mol/L, 17. 9 mL, 28. 6 mmol, 1.05 eq.) was placed in the dropping funnel, and added dropwise over 15 minutes, while the reactant solution was being stirred, and the inside temperature was being kept at -50C or below. Then, the dropping funnel was rinsed with anhydrous n-hexane (1 mL) . The obtained cream-colored suspension was stirred at -70C for 1 hour. Then, an anhydrous THF (14 mL) solution of chlorodicyclohexylphosphine (hereinafter, abbreviated as Cy2PCl) (7.0 g, 30.1 mmol, 1.1 eq.) was placed in the dropping funnel, and added dropwise over 15 minutes, while the suspension was being stirred, and the inside temperature was being kept at -50 C or below (the suspension was dissolved rapidly). After completion of the dropwise addition, the dry ice/acetone bath was taken out, and the temperature of the reaction solution was raised to room temperature over 30 minutes, followed by stirring for further 30 minutes. (Post Treatment and Purification) After the reaction solution had been concentrated under reduced pressure, toluene and an aqueous solution of sodium hydrogen carbonate (2.3 g, approximately 1 eq.) were added to the residue. The mixture was transferred to a separating funnel, shaken and allowed to stand, and the layers were separated (Aqueous Layer 1: pH=9). Then, the organic layer was further washed with water (Aqueous Layer 2: pH=7). The solvent was distilled off from the organic layer under reduced pressure, and toluene and silica gel (0.7 g) were added to the obtained light brown residue. The mixture was stirred at room temperature for 10 minutes and filtered by use of diatomaceous earth, and the residue was washed with toluene. The filtrate was concentrated, until crystals were precipitated. Then, methanol was added, and the obtained white suspension was filtered. The product obtained by the filtration was washed with methanol, and then dried under reduced pressure to give 10.6 g of title compound (2-1) as a colorless powder. Isolated Yield: 88.3%. 1H NMR (300 MHz, CDCl3): delta=8.12 (d, J=7.5 Hz, 2H), 7.76 (dt, J=1.5, 4.8 Hz, 1H), 7.57-7.47 (m, 2H), 7.38-7.28 (m, 3H), 7.23 (dt, J=0.9, 6.9 Hz, 2H), 7.02 (d, J=8.1 Hz, 2H), 1.85-1.38 (m, 12H), 1.22-0.90 (m, 10H). 31P NMR (121 MHz, CDCl3): delta=-14.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: copper(I) oxide; potassium phosphate; N,N-dimethylethylenediamine / toluene / 120 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: copper(I) oxide; N,N`-dimethylethylenediamine; potassium phosphate / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 170 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -70 - -50 °C / Inert atmosphere 2.2: 1.25 h / -50 - 20 °C | ||
Multi-step reaction with 2 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 6 h / 155 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 - 20 °C / Inert atmosphere |
Multi-step reaction with 2 steps 1.1: copper(l) iodide; potassium carbonate / 5,5-dimethyl-1,3-cyclohexadiene / 168 h / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: copper(I) oxide; potassium phosphate; N,N-dimethylethylenediamine / toluene / 120 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: copper(I) oxide; N,N`-dimethylethylenediamine; potassium phosphate / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 170 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -70 - -50 °C / Inert atmosphere 2.2: 1.25 h / -50 - 20 °C | ||
Multi-step reaction with 2 steps 1.1: copper(l) iodide; potassium carbonate / 5,5-dimethyl-1,3-cyclohexadiene / 168 h / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In tetrahydrofuran at 90℃; for 6h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 6 h / 155 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / -78 - 20 °C / Inert atmosphere |