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CAS No. : | 144970-32-1 | MDL No. : | |
Formula : | C42H32 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WAKHBSLAUKOVSZ-UHFFFAOYSA-N |
M.W : | 536.70 | Pubchem ID : | 22954523 |
Synonyms : |
|
Num. heavy atoms : | 42 |
Num. arom. heavy atoms : | 24 |
Fraction Csp3 : | 0.24 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 173.06 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -1.9 cm/s |
Log Po/w (iLOGP) : | 6.16 |
Log Po/w (XLOGP3) : | 10.81 |
Log Po/w (WLOGP) : | 8.36 |
Log Po/w (MLOGP) : | 9.86 |
Log Po/w (SILICOS-IT) : | 11.79 |
Consensus Log Po/w : | 9.4 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | -10.14 |
Solubility : | 0.0000000392 mg/ml ; 0.0000000001 mol/l |
Class : | Insoluble |
Log S (Ali) : | -10.77 |
Solubility : | 0.0000000091 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
Log S (SILICOS-IT) : | -12.78 |
Solubility : | 0.0000000001 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 5.8 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
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 |
---|---|---|
Multi-step reaction with 3 steps 1: bis-[(trifluoroacetoxy)iodo]benzene; iodine / chloroform / 24 h / 20 °C / Inert atmosphere; Sealed tube; Schlenk technique 2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / toluene / 72 h / 80 °C / Inert atmosphere; Sealed tube 3: tetrabutyl ammonium fluoride / chloroform; tetrahydrofuran / 20 °C | ||
Multi-step reaction with 3 steps 1: iodine; [bis(acetoxy)iodo]benzene 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / toluene / 10 h / Reflux 3: potassium carbonate / tetrahydrofuran; methanol / 10 h / 20 °C | ||
Multi-step reaction with 2 steps 1.1: bis-[(trifluoroacetoxy)iodo]benzene; iodine / chloroform / 24 h / 20 °C 2.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / toluene 2.2: 24 h / 20 °C |
Multi-step reaction with 3 steps 1: bis-[(trifluoroacetoxy)iodo]benzene; iodine / chloroform / 96 h / 40 °C 2: diisopropylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 24 h / 60 °C 3: potassium carbonate / methanol; chloroform; water / 24 h / 40 °C | ||
Multi-step reaction with 2 steps 1.1: iodine / chloroform / 1 h / 20 °C / Inert atmosphere 1.2: 24 h / 20 °C / Inert atmosphere 2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / toluene / 72 h / 110 °C / Inert atmosphere 2.2: 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In a 250 mL round-bottomed flask was added 1,3,5,7-tetrakis(4-iodophenyl) adamantane (22; 1.6 g, 1.69 mmol), PdCl2(PPh3)2 (82 mg, 0.11 mmol), CuI (22 mg, 0.11 mmol), ethynyltrimethylsilane (2; 5.0 mL, 35.49 mmol), anhyd toluene (40 mL), Et3N (14 mL, 101.4 mmol) under N2 atmosphere. The reaction mixture was stirred for 72 h at 110 C, after this time the mixture was filtered through a pad of Celite. The filtrate was concentrated and dissolved in CH2Cl2 (150 mL). The CH2Cl2 solution was washed with aq 10% HCl (100 mL), followed by H2O (100 mL) and brine (100 mL). The organic phase was dried (anhyd Na2SO4) and concentrated to use directly in the next step. To this crude material dissolved in MeOH (60 mL) and THF (60 mL) was added solid K2CO3 (1.21 g, 8.76 mmol). The mixture was stirred for 5 h at RT, then concentrated, and the residue was dissolved in CH2Cl2 (150 mL). The organic phase was washed with H2O (100 mL) and brine (100 mL), dried (anhyd Na2SO4) and concentrated. The residue was purified by column chromatography (PE/CH2Cl2 5:1); yield: 780 mg (85%, over 2 steps); white solid. 1H NMR (500 MHz, CDCl3): = 7.49-7.47 (d, J = 8.0 Hz, 8 H), 7.42-7.40 (d, J = 8.0 Hz, 8 H), 3.05 (s, 4 H), 2.12 (s, 12 H).23 |