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CAS No. : | 7478-69-5 | MDL No. : | MFCD00192575 |
Formula : | C18H22N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HBWITNNIJDLPLS-UHFFFAOYSA-N |
M.W : | 266.38 | Pubchem ID : | 81995 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 89.43 |
TPSA : | 6.48 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.5 cm/s |
Log Po/w (iLOGP) : | 3.3 |
Log Po/w (XLOGP3) : | 4.83 |
Log Po/w (WLOGP) : | 3.88 |
Log Po/w (MLOGP) : | 3.86 |
Log Po/w (SILICOS-IT) : | 3.35 |
Consensus Log Po/w : | 3.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.71 |
Solubility : | 0.00514 mg/ml ; 0.0000193 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.7 |
Solubility : | 0.00532 mg/ml ; 0.00002 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.58 |
Solubility : | 0.000694 mg/ml ; 0.00000261 mol/l |
Class : | Moderately soluble |
PAINS : | 1.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.08 |
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 |
---|---|---|
92% | Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 2 h; Inert atmosphere Stage #2: at 0℃; Reflux |
The synthesis of BDADPE was conducted by the classic Wittig reaction using 4,4′-bis(dimethylamino)benzophenone as substrate under an argon atmosphere (described in detail by Hirao [29]). Typically, methyltriphenylphosphonium bromide (45.58g, 127.6mmol) and freshly distilled THF (500mL) were added into a round bottom flask equipped with a reflux condenser and a magnetic bar. Potassium tert-butoxide (138.4mL of a 1.0M solution in THF, 138.4mmol) was then added dropwise to the reaction flask via constant pressure funnel. The reaction mixture was stirred for 2h at 0°C. Then the solution of 4,4′-bis(dimethylamino)benzophenone (21.4g, 79.75mmol) in dry THF (690mL) was dropped to the reaction mixture via constant pressure funnel at 0°C. The orange–brown reaction mixture was heated to reflux for 7h with stirring and then quenched with distilled water. The resultant mixture was extracted with ether three times. Such ethereal layer was washed with aqueous NaHCO3 solution and saturated aqueous NaCl solution and then dried over MgSO4. After filtration, the ethereal layer was poured into hexane to precipitate triphenylphosphine oxide. Flash column chromatography (petroleum ether/ethyl acetate 2:1 v/v) gave BDADPE in 92percent yield (19.52g, 73.37mmol) and Rf=0.76. 1H NMR (CDCl3, 400MHz): δ 2.96 (s, 12H, 2×N(CH3)2), 5.19 (s, 2H, CH2=C), 6.68–6.70 (d, 4H, aromatic proton ortho to N(CH3)2), 7.25-7.28 (d, 4H, aromatic proton meta to N(CH3)2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium hydroxide In benzene | EXAMPLE 30 Synthesis of 1,1-bis(4-dimethylaminophenyl)ethylene Into 400 ml of benzene was dissolved 10 g of 2,2-bis(4-dimethylaminophenyl)propionic acid. Thereto was added 10 g of lead dioxide and the mixture was reacted at room temperature with stirring for 30 minutes. The lead compound was removed by filtration and the benzene layer was washed with 200 ml of 5percent aqueous solution of sodium hydroxide. Benzene was removed by distillation at a reduced pressure. The residue was recrystallized from methanol to obtain 6.3 g (yield 74percent) of 1,1-bis(4-dimethylaminophenyl)ethylene, having a melting point of 123°~123.5° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With magnesium In diethyl ether; benzene | (1) Synthesis of 1,1-bis(4'-dimethylaminophenyl)ethylene After adding 100 ml of benzene to a diethyl ether solution of methylmagnesium iodide prepared from 1.7 g of magnesium, 9.9 g of methyl iodide, and 100 ml of diethyl ether, 16.6 of 4,4'-bis-dimethylaminobenzophenone was gradually added thereto. After stirring at room temperature for 10 hours, the reaction mixture was decomposed by a saturated aqueous ammonium chloride solution, followed by stirring as it was for 2 hours. After separating and water-washing an organic layer, the solvent was distilled off, and the residue was recrystallized from ethanol to obtain 10.7 g of 1,1-bis(4'-dimethylaminophenyl)ethylene. The melting point was 121° to 122° C., and the theoretical yield was 65percent. |
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