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CAS No. : | 16932-44-8 | MDL No. : | MFCD05865214 |
Formula : | C8H9IO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WCYZALIKRBYPOM-UHFFFAOYSA-N |
M.W : | 264.06 | Pubchem ID : | 11391407 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 52.14 |
TPSA : | 18.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.67 cm/s |
Log Po/w (iLOGP) : | 2.39 |
Log Po/w (XLOGP3) : | 3.16 |
Log Po/w (WLOGP) : | 2.31 |
Log Po/w (MLOGP) : | 2.37 |
Log Po/w (SILICOS-IT) : | 2.78 |
Consensus Log Po/w : | 2.6 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.74 |
Solubility : | 0.0481 mg/ml ; 0.000182 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.22 |
Solubility : | 0.16 mg/ml ; 0.000605 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.6 |
Solubility : | 0.0656 mg/ml ; 0.000248 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.11 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H317-H319 | 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 |
---|---|---|
71% | Stage #1: With n-butyllithium In diethyl ether; hexane at -35℃; for 30 h; Stage #2: With iodine In diethyl ether at 20℃; for 24 h; |
To a solution of 1,3-dimethoxybenzene (25 g, 180 mmol) in diethyl ether (150 mL) was slowlyadded butyllithium (112.5 mL of 1.6 M solution in hexanes, 180 mmol). The reaction was stirred for30 h and then cooled to -35°C. Iodine (45.7 g, 180 mmol) was added and the reaction was stirredfor 24 h at 20°C and then poured into 10percent chloridric acid (60 mL). The aqueous phase wasseparated and extracted with ethyl acetate (2 × 60 mL) and the combined organic extracts washedwith saturated aqueous sodium thiosulfate (60 mL), brine (60 mL), dried over sodium sulfate,filtered and concentrated in vacuo. The product was purified by crystallization (diethylether) to give 16 (34g, 71percent) as a white solid; mp 105-106 °C (Lit.104 °C) [1] ; 1H NMR (CDCl3): δ 3.80 (s, 6H),6.43 (d, J 8.4, 2H), 7.17 (t, J 8.4, 1H); 13C NMR (CDCl3): δ 56.6, 76.3, 103.9, 129.8, 159.5; Anal.Calcd for C8H9IO2: C, 36.39; H, 3.44; Found: C, 36.40; H, 3.46. |
66% | With n-butyllithium; iodine In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere | (1) Synthesis of intermediate 2 2,6-Dimethoxybenzene 1(50 g, 0.36 mol) was dissolved in absolute THF (500 ml). A solution of n-butyl lithium in n-hexane (166 ml, 0.42 mol) was slowly added thereto at 0°C under the nitrogen atmosphere. To the resultant solution, a solution of iodine (96.5 g, 0.38 mol) dissolved in absolute THF (200 ml) was added dropwise at 0°C over 40 minutes. The resultant solution was stirred at room temperature overnight. After completion of stirring, methanol (80 ml) was added dropwise, and the resultant mixture was concentrated under the reduced pressure, and after adding water (200 ml), the mixture was extracted with ethyl acetate (250 ml) 3 times. Organic layers were combined, and said organic layer was washed with Na2S2O3 and brine, and then dried using sodium sulfate. After drying, inorganic salt was filtered off, and the filtrate was concentrated under the reduced pressure, and the residue was washed with methanol (50 ml) 4 times and dried to obtain intermediate 2 as yellow solid. Yield: 63 g (percent yield: 66percent). |
66% | With n-butyllithium; iodine In tetrahydrofuran; hexane at 0 - 20℃; for 0.666667 h; Inert atmosphere | 2,6dimethoxybenzene (B141, 50 g0.36mol) was dissolved in the drying THF (500 mL). Thenhexane solution (166 mL, 0.42 mol) of nbutyl lithium was gradually added here at 0 degreeC under a nitrogen atmosphere. It was dropped at it at 0 degree C, having covered [ of theiodine (96.5 g0.38mol) in which the drying THF (200 mL) was dissolved ] it over the solutionobtained here for 40 minutes. The obtained solution was stirred at the room temperature allnight. After condensing under decompression of the mixture obtained by dropping methanol(80 mL) after an end and adding water (200 mL), ethyl acetate (3x250 mL) extracted. After itcollected organic layers and Na S O and a salt solution washed the organic layer, it dried usingsodium sulfate.Mineral salt was filtered after drying and it condensed under decompression, and when residuewas washed 4 times and dried with methanol (50 mL), the 2,6dimethoxyiodobenzene (B142) was obtained as a yellow solid (63 g0.24mol, 66percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With N-iodo-succinimide; palladium diacetate In N,N-dimethyl-formamide at 80℃; for 3 h; Inert atmosphere | General procedure: A solution of 2,6-dimethoxybenzoic acid (0.1 mmol), iodine reagent, palladium catalyst, solvent (1.0 mL) was added to 10 mLIn the reaction vessel,Access to nitrogen protection,Heating reaction,The product was analyzed by GC-MS. The specific reaction conditions of each control group were shown in Table 1. |
37% | With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium iodide In dimethyl sulfoxide at 160℃; for 24 h; Schlenk technique | Silak reaction tube equipped with a magnetic stirrer was charged with 3.1 mg of silver sulfate,36.3 mg of copper acetate, 36.4 mg of 2,6-dimethoxybenzoic acid,149.9 mg of sodium iodide and 1 mL of dimethylsulfoxide.The reaction was heated at 160 ° C for 24 hours in the presence of oxygen.After the reaction was completed, distilled water was added to quench the reaction,Extraction with ethyl acetate 3 times, each time 10mL,The combined organic phases are concentrated,19.5 mg of 2,6-dimethoxy-iodobenzene was obtained in a yield of 37percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: With copper(l) iodide; diisopropylamine In toluene at 20 - 60℃; for 49 h; Inert atmosphere Stage #2: With methanol; sodium hydroxide In tetrahydrofuran at 20℃; for 1 h; Inert atmosphere |
Example 15; 1 ) Me3SiCCH,9I (93percent)[0125] 2,6-Dimethoxyphenylacetylene (91). To a stirred, degassed solution of 2-iodo-l ,3- dimethoxybenzene (13.2 g, 50 mmol), trans-dichlorobis(triphenylphosphine)palladium(II) (702 mg, 1 mmol), triphenylphospine (524 mg, 2 mmol), and copper(I) iodide (288 mg, 1.5 mmol) in 3 : 1 (v/v) toluene : diisopropylamine (200 mL) under argon is addedtrimethylsilylacetylene (8.0 mL, 57 mmol). The resulting mixture is stirred under argon at room temperature for lh, followed by 48 hour at 60°C, during which period a heavy precipitate attributed to iPr2NHHI is formed. Contents are passed on a Si02 plug with ethyl acetate as eluent. Volatiles are evaporated under reduced pressure, and the contents are passed on a short Si02 column with 95 :5 to 90: 10 pentane : ethyl acetate (v/v) as the eluent to afford the crude TMS-protected alkyne as an off-white solid that is directly carried to the next step without further purification. The solid is dissolved in THF (90 mL) and the solution is degassed by bubbling argon gas through for ca. 30 min. To the stirred mixture is added by a solution of sodium hydroxide (6 g) in methanol (30 mL). The reaction mixture is stirred at room temperature for lh, before pouring of the contents in saturated aqueous NaCl. After extration with diethyl ether and evaporation of the volatiles, the crude alkyne is purified by passage through a short Si02 column using 1 : 1 dichloromethane : pentane (v/v) as the eluent to afford alkyne 91 as a beige solid (7.55 g, 93percent over 2 steps). 1H-NMR (CDC13, 300 MHz): δ = 7.25 (t, J = 8.4 Hz, 1H), 6.54 (d, J = 8.4 Hz, 2H), 3.89 (s, 6H), 3.57 (s, 1H). 13C-NMR (CDC13, 75 MHz): δ =161.9, 130.2, 103.2, 99.9, 85.3, 76.3, 55.9. Characterization data for 91 are consistent with literature values (See Wayland, B. B.; Sherry, A. E.; Poszmic, G.; Bunn, A. G. J. Am. Chem. Soc. 1992, 1 14, 1673-1681). |
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