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CAS No. : | 206762-48-3 | MDL No. : | |
Formula : | C22H34O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ASYHPQABVPFLJM-UHFFFAOYSA-N |
M.W : | 362.50 | Pubchem ID : | 86198656 |
Synonyms : |
|
Num. heavy atoms : | 26 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.64 |
Num. rotatable bonds : | 16 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 107.89 |
TPSA : | 52.6 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -3.87 cm/s |
Log Po/w (iLOGP) : | 4.76 |
Log Po/w (XLOGP3) : | 6.54 |
Log Po/w (WLOGP) : | 6.01 |
Log Po/w (MLOGP) : | 3.19 |
Log Po/w (SILICOS-IT) : | 7.04 |
Consensus Log Po/w : | 5.51 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.32 |
Solubility : | 0.00173 mg/ml ; 0.00000476 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -7.44 |
Solubility : | 0.0000131 mg/ml ; 0.0000000361 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -7.36 |
Solubility : | 0.0000159 mg/ml ; 0.0000000438 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 3.13 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
96% | With sodium hydride In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With potassium <i>tert</i>-butylate In tetrahydrofuran; <i>tert</i>-butyl alcohol at 40℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With potassium <i>tert</i>-butylate; tetra(n-butyl)ammonium hydroxide In tetrahydrofuran; methanol; <i>tert</i>-butyl alcohol at 50℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | Stage #1: 1,4-di-(n-heptyloxy)benzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at -78 - 0℃; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane for 16h; Heating; Stage #3: With hydrogenchloride In diethyl ether; hexane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With potassium <i>tert</i>-butylate; tetra(n-butyl)ammonium hydroxide In tetrahydrofuran; methanol; <i>tert</i>-butyl alcohol at 50℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 26 percent / potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 0.25 h / 40 °C 2: 21 percent / potassium tert-butoxide; tetra-n-butylammonium hydroxide / 2-methyl-propan-2-ol; tetrahydrofuran; methanol / 0.33 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With hydrazine In tetrahydrofuran; chloroform at 25℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With indium(III) chloride at 20℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34.9% | Stage #1: methyl-3-pyridylketone; 2,5-di-(n-heptyloxy)terephthaldialdehyde With potassium hydroxide In ethanol at 20℃; Stage #2: With ammonium hydroxide In ethanol at 20℃; for 70h; | General procedure for the synthesis of the bis(3,2′:6′,3″-terpyridine) ligands General procedure: The appropriate 2,5-dialkyloxybenzene-1,4-dicarbaldehyde (1.0 eq) was placed at roomtemperature in EtOH (25-50 mL). 3-Acetylpyridine (5.0 eq) and crushed KOH (5.0 eq) werethen added. Immediate color change upon the addition of KOH from yellow to orange/redobserved. Then slow addition of aqueous NH3 solution (32%, 120 eq) followed and thereaction mixture was stirred at room temperature for 21-96 h. The fine precipitate thatformed was collected by filtration and washed with H2O (3 x 7-15 mL), followed by EtOH (3 x7-15 mL) and Et2O (2x 7-15 mL) and then dried in vacuo. The off-white/ light yellow crudesolid was recrystallized/ reprecipitated from a mixture of EtOH and CHCl3, MeOH and CHCl3or EtOH to give the desired bis(3,2′:6′,3″-terpyridine) ligand. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18.1% | Stage #1: 1,4-dibromo-2,5-bis(heptyloxy)benzene With n-butyllithium In diethyl ether; hexane at 0℃; for 2h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at 0 - 20℃; for 18h; Inert atmosphere; | Compound 7b Compound 7b has previously been reported [5], but the following synthesis is convenient. Compound 7a (1.84 g, 3.96 mmol, 1.0 eq) was dissolved in dry Et2O (100 mL) and the solution was cooled to 0 °C under N2. nBuLi (15% in hexanes, 1.6 M, 9.9 mL, 16 mmol, 4.0 eq) was added at 0 °C over a period of 15 min and the reaction mixture was stirred at 0 °C for 2 h. Dry DMF (1.2 mL, 16 mmol, 4.0 eq) was added and the reaction mixture was stirred for 18 h, allowing the mixture to slowly warm from 0 °C to room temperature. The now light yellow suspension was quenched by the addition of saturated aqueous NH4Cl (150 mL) and subsequently extracted with chloroform (3 x 100 mL). The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography (silica, EtOAc in cyclohexane 0-13% gradient. The yellow product was recrystallized from petroleum ether (4 mL) and the resultant crystals were collected by filtration, washed with petroleum ether and dried in vacuo to give 7b (260 mg, 0.717 mmol, 18.1%) as a yellow crystalline solid. 1H NMR (500 MHz, CDCl3): δ/ppm 10.52 (s, 2H, HCHO), 7.43 (s, 2H, H3), 4.09 (t, J = 6.5 Hz, 4H, Ha), 1.87 - 1.79 (m, 4H, Hb), 1.51 - 1.43 (m, 4H, Hc), 1.40 - 1.28 (overlapping m, 12H, Hd+e+f), 0.90 (t, J = 6.9 Hz, 6H, Hg). 13C{1H} NMR (126 MHz, CDCl3): δ/ppm 189.6 (CCHO), 155.4 (C2), 129.4 (C1), 111.8 (C3), 69.4 (Ca), 31.9 (Ce), 29.2 (Cb), 29.1 (Cd), 26.1 (Cc), 22.7 (Cf), 14.2 (Cg). The NMR spectroscopic data agreed with the literature [5]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere 2.1: n-butyllithium / diethyl ether; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 18 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere 2.1: n-butyllithium / diethyl ether; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 18 h / 0 - 20 °C / Inert atmosphere |