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CAS No. : | 1968-05-4 | MDL No. : | MFCD00195766 |
Formula : | C17H14N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VFTRKSBEFQDZKX-UHFFFAOYSA-N |
M.W : | 246.31 | Pubchem ID : | 3071 |
Synonyms : |
DIM;Arundine;HB 236
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.06 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 79.61 |
TPSA : | 31.58 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -4.89 cm/s |
Log Po/w (iLOGP) : | 1.99 |
Log Po/w (XLOGP3) : | 4.1 |
Log Po/w (WLOGP) : | 4.24 |
Log Po/w (MLOGP) : | 3.0 |
Log Po/w (SILICOS-IT) : | 5.01 |
Consensus Log Po/w : | 3.67 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.52 |
Solubility : | 0.00745 mg/ml ; 0.0000303 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.47 |
Solubility : | 0.00837 mg/ml ; 0.000034 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -7.1 |
Solubility : | 0.0000197 mg/ml ; 0.00000008 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.91 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P273-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335-H412 | 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 |
---|---|---|
73% | With sulfuric acid In methanol for 5 h; Reflux | A solution of 25.0 g (101.5 mmol) of 3,3-methylenediindole and 15.1 g (101.5 mmol) of triethyl orthoformate in 400 ml of methanol was added with 1.4 ml of concentrated sulfuric acid and stirred for 5 h while refluxing under heating. The reaction solution was cooled in an iced water bath. The precipitate was collected by filtration and washed with 500 ml of methanol, to obtain 19.0 g of brown solid, which was identified as the following intermediate 2-2 by FD-MS analysis (yield: 73percent). |
69.9% | With sulfuric acid In methanol for 1.05 h; Reflux | In a 2000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 50.69 g (0.2058 mole) of 3,3'-methylenediindole and 30.55 g (0.2061 mole) of triethyl orthoformate, then 640 g of methanol was added, and the mixture was stirred. To the mixture was added dropwise 5.0 g (0.0515 mole) of concentrated sulfuric over 3 minutes and the mixture was heated under reflux for 1 hour. The mixture was cooled to room temperature and the reddish brown crystals formed were collected by filtration and reslurried twice with 500 ml of methanol. The solvent was distilled off under reduced pressure and 36.81 g of solid C or indolo[3,2-b]carbazole (0.1438 mole, 69.9 percent yield) was obtained as a reddish brown powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.1% | With toluene-4-sulfonic acid; In ethanol; water; at 40 - 50℃; for 3h; | Add 280 grams of water to the 1L three-neck bottle. 120 grams of ethanol, 100.0 grams, 15.4 g of paraformaldehyde and 14.7 g of p-toluenesulfonic acid, The reaction was carried out at 40-50 C for 3 hours, and the stirring was stopped after the reaction was almost complete by TLC. Filtration and washing with ethanol to obtain crude 3,3'-dimethane. The crude product was recrystallized by heating with toluene as a solvent. After the precipitate is completely cooled, it is crystallized and filtered. Dry under low temperature vacuum to obtain 99.0 g of a white solid. The yield was 94.1%. |
92% | With bromine; In acetonitrile; at 50℃; for 16h; | General procedure: A 25-mL flask, equipped with a magnetic stirring bar, was charged with 1H-indole 1a (117mg, 1.0mmol), CH3CN (4.0mL), and benzaldehyde 2a (0.056mL, 0.55mmol), followed by addition of a solution of Br2 (0.0010mL) in CH3CN (1.0mL). The reaction mixture was stirred at 50C for 1min. After 1a was consumed, as indicated by thin-layer chromatography (TLC), the reaction mixture was quenched with aqueous Na2S2O3, cooled to room temperature, poured into 30mL water under stirring, and extracted with CH2Cl2 three times. The extract was dried over anhydrous MgSO4. After removal of solvents, the residue was purified by column chromatography on silica gel (petroleum ether-ethyl acetate=9/1, V/V) to afford the product 3a as a pink solid (158mg, 98% yield). |
90% | With immobilized hexamine on Fe3O4/SiO2 core/shell nanoparticles tribromide; In neat (no solvent); at 80℃; for 0.166667h; | General procedure: A mixture of aldehyde or ketone (1 mmol), indole (2 mmol), and catalyst (0.01 g) was stirred at 80 C for 10 min. The reaction was monitored by TLC. After completion of the reaction, EtOH (3 mL) was added and the catalyst was separated by an external magnet. In the recycling experiment, the separated catalyst was then washed with ethanol and dried in oven to remove residual solvent. The results of synthesis of BIMs under solvent-free conditions at 80 C, are presented in Table 1. |
56% | With tungsto-vanadophosphoric acid on the surface of pyridine modified Fe3O4 nanoparticle; In neat (no solvent, solid phase); at 100℃; for 0.25h; | General procedure: A mixture of carbonyl compound (1 mmol), indole (0.234 g,2 mmol) and the desired amount of the inorganic-organic hybridmaterial HPA/TPI-Fe3O4nanoparticles was stirred at elevated tem-perature (100C) for an appropriate reaction time. After completionof the reaction, as indicated by TLC, acetonitrile (3 ml) was added tothe reaction mixture and the catalyst was removed using an exter-nal magnetic bar. Then, silica gel (?1 g) was added to the filtrate,and after evaporation of the solvent, a dark pinkish solid mixturewas obtained. Purification of the product was performed by shortcolumn chromatography eluted with ethylacetate/petroleum ether(1/9) to give a pinkish solid product in high yield. Products wereknown compounds and were identified by means of IR and1H NMRspectroscopy and/or comparison of their melting points with thosereported in the literature. |
42% | With Fe3O4(at)C-PW (12-Tungstophosphoric acid immobilized on carbon-coated Fe3O4 nanoparticles); In water; at 20℃; for 0.5h; | General procedure: A mixture of aldehyde (1 mmol), indole (2 mmol), catalyst (0.15 g), and H2O (5 mL) was stirred at room temperature. At the end of the reaction, water was removed from the mixture by centrifugation followed by decantation. The product was dissolved in acetonitrile, and the catalyst was separated from the product by an external magnet. The solvent was evaporated in vacuum to give the product, which was purified by column chromatography on silica gel using EtOAc/petroleum ether as eluent. |
40% | With boron trifluoride diethyl etherate; In diethyl ether; at 20℃; for 2h; | General procedure: BF3·Et2O (21.3 mg, 0.15 mmol) was added to a mixture of indole 1 (234.4 mg, 2 mmol) and benzaldehyde 2a (106.1 mg, 1 mmol) in diethyl ether (2 mL). The reaction mixture was stirred at room temperature for 2 h in the atmosphere and monitored by TLC. After completion of the reaction, the volatile components were removed using a vacuum rotary evaporator. The resulting residue was purified by column chromatography on silica gel column using EtOAc/petroleum ether solution (1:15-1:8, v/v) as eluent to afford a pink solid bis(indolyl)phenylmethane 3a |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium triflate; at 80℃; for 24h; | In this example, 0.5 mmol of indole was added to 2.5 mL of methanol,Further, 1.0 molpercent of the above catalyst based on the molar amount of indole,One equivalent of base was added to indole to prepare a reaction solution,The reaction solution was kept in the air at 60 ° C. for 20 hours,Synthesis of indole derivatives according to the following formula was carried out. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | dmap; In tetrahydrofuran; | (b) 1,1'-DiBOC-<strong>[1968-05-4]3,3'-diindolylmethane</strong> (56). To a solution of 55 (2.0 g, 8.12 mmol) and (t-BuOOC)2O (3.9 g, 17.87 mmol) in THF (20 mL) was added a catalytic amount of DMAP and stirred for overnight under argon. The solvent was evaporated to give a crude product. Flash chromatography (3percent EtOAc/hexane) yielded 56 as a white solid (3.44 g, 95percent): 1H NMR (300 MHz, CDCl3) delta 1.65 (s, 18, OC(C3)3), 4.09 (s, 2, C2), 7.21 (m, 2, ArH), 7.31 (m, 2, ArH), 7.38 (s, 2, PyH), 7.53 (m, 2, ArH), 8.12 (br.d, J=8.6 Hz, 2, ArH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.1%; 45% | With acetic acid; In water; at 50 - 90℃; for 3 - 20h; | The one carbon-linked bis-indoles (la-g) were synthesized from indole or 5-substituted indole and formaldehyde, using the method of Jackson et al. (J. Chem. Soc. Perkin Trans. I, 1987, 11: 2543-51 (Scheme 4).R B:HOCH3CO2H HCO2H OHScheme 4 Synthesis of 1C bis-indoles. Ia and Ib produced as a mixture, as were Ic and Id. EPO <DP n="81"/>[00321] Formaldahyde (0.55 eq., 37percent aqueous solution) and acetic acid (0.5 eq.) were added to indole or substituted indole (1.0 - 100 mmol) suspended in H2O and the suspension heated at 9O0C for 8-20 hrs. (Scheme 4). Since 5-hydroxy-indole is sensitive to oxidation, the synthesis of Ig was performed under argon and excluding light, and was heated at only 5O0C for 3 hrs. For the reaction giving la,b, as well as that for lc,d, the beige, gummy mixture was collected by vacuum filtration, washed with water, recrystallized from EtOAc/hexanes and the resulting cream solid purified by flash chromatography using 4: 1 hexanes/EtOAc as eluant. Purification of le-g are given below.Di-(indol-3-yl)methane (Ia):[00322] White crystals (5.55g, 45percent); mp 158-16O0C; 1H NMR: 4.13 (s, 2H),6.91 (t, 2H, J=7.3), 7.03 (t, 2H, J=7.3), 7.13 (s, 2H), 7.31 (d, 2H, J=8.2), 7.51 (d, 2H,J=7.6), 10.72 (s, 2H); 13C NMR: 20.94, 111.32 (2C), 114.21 (2C), 118.04 (2C),118.69 (2C), 120.76 (2C), 122.77 (2C), 127.21 (2C), 136.41 (2C); EI m/z (percent): 246.4(6), 117.8 (100), 89.6 (49); HRMS: CnHi4N2 requires 246.1157, found 246.1147.; 3 -((indol-1-yl) methyl) -indole (\\b):[00323] White crystals (0.262g, 2.1percent); mp 82-840C; 1H NMR: 5.50 (s, 2H),6.38 (d, IH, J=0.6), 7.02 (m, 4H), 7.34 (d, IH, J=8.2), 7.49 (m, 4H), 7.64 (d, IH,J=8.2), 11.03 (s, IH); 13C NMR: 41.29, 100.30, 110.27, 111.02, 111.61, 118.56,118.80 (2C), 120.38, 120.84, 121.29, 124.84, 126.50, 128.30, 128.84, 135.66, 136.36;EI m/z (percent): 246.4 (8), 117.6 (100); HRMS: CnH14N2 requires 246.1157, found246.1168. |
25%Chromat.; 65%Chromat. | With calcium oxide; In neat (no solvent); at 100℃; for 3h; | Indole 1 (8.54 mmol), paraformaldehyde (10.25 mmol) and CaO (145.18 mmol) were blendedwith a magnetic stirrer for the period indicated (TLC) at 100 °C. After reaction, the crude mixture wasextracted with CH2Cl2 and the obtained extract was passed through celite. The concentrated filtratewas ash chromatographed (hexane/ethyl acetate 3/1) on silica gel, obtaining the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With copper diacetate; palladium diacetate; at 70℃; for 12h;Neat (no solvent); | General procedure: A mixture of substituted indoles (2 mmol), Cu(OAc)2 (1.2 mmol), Pd(OAc)2 (0.1 mmol) and tertiary amines (1.3 mmol) was stirred at 70 °C for 12 h under neat condition. The reaction mixture was dissolved in ethyl acetate and filtered through a plug of Celite. The residue was washed with ethyl acetate (2 .x. 20 mL). The filtrate was washed with 100 mL of water and 10 mL of 0.5 N HCl and the organic layer was collected. The aqueous phase was extracted with ethyl acetate (3 .x. 20 mL). The combined organic phase was washed with saturated sodium chloride solution (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography with ethyl acetate (EA) and petroleum ether (Pet) as eluent to afford the corresponding products and appropriate yield is shown in [Table 2] and [Table 3]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; aq. phosphate buffer; at 24.99℃;pH 7.2; | General procedure: The inclusion complex formation phenomenon of CDs with guest DIMs in aqueous phosphate buffer solutions was examined at pH 7.2 by means of UV?visible spectral titration in a Shimadzu 1700 Spectrophotometer (Shimadzu Corporation, Kyoto, Japan). A 1.0 mM stock solution of DIMs (5.0 ml) was prepared in methanol, and 6.0 ll of this stock solution was added to the phosphate buffer solution to maintain the final concentration of molecules as 2.5 10 7 mol dm 3 in the cuvette. Then gradually a-, b-, c-CD were added in the cuvette so that the concentrations of CDs ranged from 0 to 12.5 10 3 mol dm 3. The absorption spectra were measured against an appropriate reagent blank. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; aq. phosphate buffer; at 24.99℃;pH 7.2; | General procedure: The inclusion complex formation phenomenon of CDs with guest DIMs in aqueous phosphate buffer solutions was examined at pH 7.2 by means of UV?visible spectral titration in a Shimadzu 1700 Spectrophotometer (Shimadzu Corporation, Kyoto, Japan). A 1.0 mM stock solution of DIMs (5.0 ml) was prepared in methanol, and 6.0 ll of this stock solution was added to the phosphate buffer solution to maintain the final concentration of molecules as 2.5 10 7 mol dm 3 in the cuvette. Then gradually a-, b-, c-CD were added in the cuvette so that the concentrations of CDs ranged from 0 to 12.5 10 3 mol dm 3. The absorption spectra were measured against an appropriate reagent blank. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; aq. phosphate buffer; at 24.99℃;pH 7.2; | The inclusion complex formation phenomenon of CDs with guest DIMs in aqueous phosphate buffer solutions was examined at pH 7.2 by means of UV?visible spectral titration in a Shimadzu 1700 Spectrophotometer (Shimadzu Corporation, Kyoto, Japan). A 1.0 mM stock solution of DIMs (5.0 ml) was prepared in methanol, and 6.0 ll of this stock solution was added to the phosphate buffer solution to maintain the final concentration of molecules as 2.5 10 7 mol dm 3 in the cuvette. Then gradually a-, b-, c-CD were added in the cuvette so that the concentrations of CDs ranged from 0 to 12.5 10 3 mol dm 3. The absorption spectra were measured against an appropriate reagent blank. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With ethylaluminum dichloride; In hexane; dichloromethane; at 20℃; for 24h;Inert atmosphere; | General procedure: A 1 M solution of EtAlCl2 in hexane (2 mmol, 2 mL) wasadded dropwise to a stirred and cooled (0 °C) mixture of methyl2-acetamidoacrylate (172 mg, 1.2 mmol) and the suitable3-substituted indole (1 mmol) in dry CH2Cl2 (10 mL) under anitrogen atmosphere. The mixture was stirred at room temperaturefor 17?72 hours, then carefully poured into an ice-coldsaturated aqueous sodium hydrogen carbonate solution (10 mL).The resulting suspension was filtered through Celite and theaqueous layer was extracted with dichloromethane (3 × 15 mL).The combined organic layers were dried over sodium sulfate,filtered and concentrated in vacuo. The crude product was purifiedby flash chromatography on silica gel (cyclohexane/ethylacetate 8:2, or CH2Cl2/methanol 98:2 for 3h, as eluent) and/orcrystallization. |
[ 5275-04-7 ]
3-(Pyridin-3-ylmethyl)-1H-indole
Similarity: 0.97
[ 5275-07-0 ]
3-Pyridin-4-ylmethyl-1H-indole
Similarity: 0.97
[ 5275-04-7 ]
3-(Pyridin-3-ylmethyl)-1H-indole
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H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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