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CAS No. : | 18711-13-2 | MDL No. : | MFCD00047214 |
Formula : | C8H3Cl2NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NUXYYWOWNFEMNH-UHFFFAOYSA-N |
M.W : | 216.02 | Pubchem ID : | 2734793 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 52.18 |
TPSA : | 46.17 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) : | -6.22 cm/s |
Log Po/w (iLOGP) : | 1.08 |
Log Po/w (XLOGP3) : | 1.97 |
Log Po/w (WLOGP) : | 1.56 |
Log Po/w (MLOGP) : | 1.33 |
Log Po/w (SILICOS-IT) : | 2.78 |
Consensus Log Po/w : | 1.74 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.76 |
Solubility : | 0.374 mg/ml ; 0.00173 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.57 |
Solubility : | 0.588 mg/ml ; 0.00272 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.02 |
Solubility : | 0.0208 mg/ml ; 0.0000962 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.76 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
In ethanol; at 110 - 150℃; for 50h; | Example II-87: (5-Hydroxy-1H-pyrazol-3-yl)-acetic acid [(3Z)-4,7-dichloro-2-oxo-1,2-dihdyro- indol-3-ylidene]-hydrazide (06I6L (5-HYDROXY-1H-PYRAZOL-3-YL3-ACETIC acid hydrazide (56 mg, 0. 36 mmol) and the isatin (45 mg, 0.30 mmol) were suspended in absolute ethanol (-2-5 mL) in A closed vial and stirred in a 110 C oil bath for 2 days and, if needed, an additional 2 h at 150 C. The warm reaction mixture was evaporated with a stream of nitrogen to about one-fourth volume and acetic acid (-1-3 mL) was added and warmed to partially dissolve the solids. After cooling, the yellow solids were collected and washed with ethanol, and dried. This process was repeated if necessary. [0617] 1HNMR (400 MHz, D6-DMSO) o 12.60 (s, 1 H), 11.85 (s, 1 H), 11.5 (br s, 1 H), 9.5 (br s, 1 H), 7.44 (d, 1 H), 7.16 (d, 1 H), 5.40 (s, 1H), 4.0 (br s, 2H); LCMS-APCI m/z 354 [M+1] +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With acetic acid; at 100℃; for 3h; | Example II-96 : (2-Oxo-1, 2-dihydro-pyrimidin-5-yl)-acetic acid [(3Z)-4,7-dichloro-2-oxo-1,2- DIHYDRO-INDOL-3-YLIDENE]-HYDRAZIDE [0639] The (at)TURE OF (2-OXO-1,2-DIHYDRO-PYRIMIDIN-5-YL)-ACETIC ACID HYDRAZIDE (67 MG, 0. 4 mmol) and 4,7-dichloro-isatin (95 mg, 0.44 mmol) in AcOH (10 mL) was stirred at 100"C FOR 3 h. After removal of the solvent, the residue was CRYSTALLIZED FROM MEOH TO GIVE THE TITLE compound as yellow solid (45 mg, 31%). [0640] H-NMR (400 MHz, DMSO-d6) 612. 68 (s, 1H), 11.92 (s, 1H), 8.41 (s, 2H), 7.46 (d, 1H), 7.16 (d, 1H), 4.00 (s, 2 H); MS (m/z) 366 [M+1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | diethylamine; In methanol; at 20℃; | In these schemes, ketone (4.0 equv.) and a catalytic amount of diethylamine (10 drops) are added to a solution of substituted isatin (1.0 equv.) in methanol (5 mL). The mixture is stirred at room temperature until starting material (substituted isatin) disappears completely. The resulting solution is concentrated and applied to flash chromatography eluting with hexane / ethyl acetate to afford pure product in quantitative yield. Further purification is done by recrystallization with hexane / ethyl acetate.; 4,7-Dichloro-3-[2-(4-chlorophenyl-2-oxoethyl)]-3-hydroxyI-l,3-dihydroindol-2-one (YK-4-275): white solid; mp 194-196 0C; 1H NMR (DMSO, 400 MHz) delta 10.96 (s, IH), 7.93 (d, 2H, J = 8.8 Hz), 7.57 (d, 2H, J = 8.8 Hz), 7.30 (d, IH, J = 8.8 Hz), 6.90 (d, IH5 J = 8.8 Hz), 6.47 (s, IH), 4.36 (d, IH, J= 18.4 Hz), 3.71 (d, IH5 J= 18.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In N,N-dimethyl-formamide; mineral oil; | A. Synthesis of 4,7-dichloro-1-pentyl-1H-indole-2,3-dione To a mixture of sodium hydride (0.17 g, 6.94 mmol, 60% dispersion in mineral oil) in anhydrous N,N-dimethylformamide (5.00 mL) was added a solution of 4,7-dichloro-1H-indole-2,3-dione (1.00 g, 4.60 mmol) in N,N-dimethylformamide (5.00 mL) at 0 C. The brown reaction mixture was stirred for 0.5 h followed by the addition of a solution of 1-bromopentane (0.84 g, 5.55 mmol) in anhydrous N,N-dimethylformamide (5.00 mL). The reaction mixture was stirred at ambient temperature for 16 h and poured into wet ethyl ether (30.0 mL). After the organic layer was separated, it was washed with water (2*20.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The gummy residue was dried under vacuum and the solid was triturated with ether to give the title compound (0.98 g, 98%): MS (ES+) m/z 286.2 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a mixture of sodium hydride (0.17 g, 6.94 mmol, 60% dispersion in mineral oil) in anhydrous N, Lambda/-dimethylformamide (5.00 mL) was added a solution of 4,7- dichloro-1/-/-indole-2,3-dione (1.00 g, 4.60 mmol) in N, Lambda/-dimethylformamide (5.00 mL) at 0 0C. The brown reaction mixture was stirred for 0.5 h followed by the addition of a solution of 1-bromopentane (0.84 g, 5.55 mmol) in anhydrous N, Lambda/-dimethylformamide (5.00 mL). The reaction mixture was stirred at ambient temperature for 16 h and poured into wet ethyl ether (30.0 mL). After the organic layer was separated, it was washed with water (2 x 20 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The gummy residue was dried under vacuum and the solid was triturated with ether to give the title compound (0.98 g, EPO <DP n="192"/>98%): MS (ES+) m/z 286.2 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With epiCDT; In diethyl ether; at 20℃; for 2h; | General procedure: alpha-Isothiocyanato imide 2c (10.7 mg, 0.050 mmol) and catalyst 6d (2.8 mg, 0.005 mmol, 10 mol %) were dissolved in diethyl ether (1.0 mL) in a glass vial while stirring. Isatin 1a (8.8 mg, 0.060 mmol) was added and the mixture was further stirred at room temperature for 2 h. The reaction progress was monitored by TLC analysis. Upon completion, the solvent was removed under reduced pressure and the crude product was purified by flash column chromatography on silica gel (1:1 hexane/ethyl acetate) to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 9-epi-9-amino-9-deoxyquinine; water; benzoic acid; In tetrahydrofuran; at 5℃; for 5h; | General procedure: To a mixture of isatin 1a (14.7 mg, 0.1 mmol), H2O (5.4 muL, 0.3 mmol), quinine-derived amine 3 (3.3 mg, 0.01 mmol), and benzoic acid (3.66 mg, 0.03 mmol) in THF (1.0 mL) at 5 C was added acetaldehyde (22.0 mg, 0.5 mmol). After the reaction mixture was stirred for 15 h at this temperature, it was cooled to 0 C. Methanol (2 mL) and NaBH4 (20.0 mg, 0.5 mmol) were then added sequentially. The resulting reaction mixture was stirred for an additional 30 min at 0 C. Water (5.0 mL) was added to quench the reaction. The reaction mixture was extracted with ethyl acetate (10 mL x 3). The combined organic phases were dried over Na2SO4. After filtration and removal of the solvent under reduced pressure, the crude product was purified by column chromatography on silica gel (ethyl acetate/hexane 1:2 to 2:1) to give the pure product 2a. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With cetyltrimethylammonim bromide; In water; at 80℃; for 0.5h;Green chemistry; | General procedure: A mixture of isatin derivative (1.0 mmol), trans-4-hydroxy-L-proline (0.131 g,1 mmol), and CTAB (4 mmol) in water (50mL) was stirred at 80 C for 30 min. After completion of the reaction (monitored by TLC), the contents were filtered and the residue was washed thoroughly with water until free from CTAB. Finally, the residue was crystallized from a chloroform-petroleum ether mixture to afford the desired products in excellent yields. The characterizations of the products were accomplished by spectroscopic analysis (1H, 13C NMR, FTIR, and ESI-mass) and also by comparison of the data reported in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With 1,4-diaza-bicyclo[2.2.2]octane; In tetrahydrofuran; at 20℃; for 6h;Inert atmosphere; | General procedure: To the stirred solution of beta-keto ester 2(aei) (1.0 mmol) and DABCO (30 mol %) in 5 mL THF was added isatin 1(aeh) (1 mmol).The mixture was then stirred at room temperature for stipulated time (5-8 h). After completion of reaction as indicated by TLC, thesolvent was removed at reduced pressure on a BUCHI rotary evaporator. The residue was then purified by column chromatography on silica gel (hexane/ethyl acetate4:1 to 1:1) to afford thedesired product 3(a-w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In toluene; at 70℃; for 3h; | General procedure: To a solution of isatin 1 (1 mmol) in toluene (5 mL) was added the solution of trialkyl/aryl Al 2 (2 mmol, 2 M in toluene) dropwise at RT. Then the mixture was heated at 70 C and stirred for additional 3-3.5 h (see Table 2). The reaction was monitored by TLC. After completion of the reaction, toluene was evaporated and extracted with ethyl acetate (3 × 5 mL). The combined organic layer was washed with brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography using ethyl acetate/hexanes (4:1-1:1). All compounds were characterized by (MP, NMR, Mass, and IR) spectral data.18 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With diethylamine; In methanol; at 20℃; | Example 1- Synthesis of 4,7 dichloroisatin analogs [0143] An appropriate acetophenone and 4, 7-dichloroisatin were condensed in the presence of a catalytic amount of diethylamine to prepare the desired compound in quantitative yield. Example compounds: R1 = 4'-CN (PT-1-11); 2'-OCH3 (PT-1-12) ; 3*-OCH3 (PT-1-18) ; 2',4'-OCH3 (PT-1-19); 2',3*-OCH3 (PT-1-20); 3*,4OCH3 (PT-1-21); 3*,5*OCH3 (PT-1-22); 2',3*,4',-OCH3 (PT-1-23); 3*,4',5*-OCH3 (PT-1-13); 4'-OC2H5 (PT-1-14); 4'-CF3 (PT-1-15); 4'- OCF3 (PT-1-16); 4'-N(CH3)2 (PT-1-17); 4'-OPh (PT-1-60); 4'-SCH3 (PT-1-67); and 4'-C(CH3)2 (PT-1-67). |
100% | With diethylamine; In methanol; at 20℃; | General procedure: Example 1- Synthesi s of 4,7 dichloroisatin analogs [0176] An appropriate acetophenone and 4, 7-dichloroisat were condensed in the presence of a catalytic amount of diethylamme to prepare the desired compound in quantitative yield. Example compounds: R1 = 4'-CN (PT-1-11); 2'-GCH3 (PT-1-12) ; 3'- OCH3 (PT-1 -18) ; 2 FontWeight="Bold" FontSize="10" ,4'-OCH3 (PT-1-19); 2,.3'-( }( 1 i ·. (PT-1-20); 3',4OCH3 (PT-1 -21 ); 35'OCH3 (PT-1-22); 2,,3',4',-OCH3 (PT-1-23); 3'A 5'-OCH3 (PT-1-13); 4'-OC2H5 (PT-1- 14); 4 -CF3 (PT-1-15); 4'-OCF3 (PT-1-16); 4'-N(CH3)2 (PT-1-17); 4'-OPh (PT-1-60); 4'-SCH3 (PT-1-67); and 4'-C(CH3)2 (PT-1-67). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With titanium tetrachloride; zinc; In tetrahydrofuran; at 20℃; for 0.0833333h;Inert atmosphere; | General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4. |
Tags: 18711-13-2 synthesis path| 18711-13-2 SDS| 18711-13-2 COA| 18711-13-2 purity| 18711-13-2 application| 18711-13-2 NMR| 18711-13-2 COA| 18711-13-2 structure
[ 1677-48-1 ]
5,6-Dichloroindoline-2,3-dione
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[ 1677-48-1 ]
5,6-Dichloroindoline-2,3-dione
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[ 1677-48-1 ]
5,6-Dichloroindoline-2,3-dione
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[ 1677-48-1 ]
5,6-Dichloroindoline-2,3-dione
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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 |
Sorry,this product has been discontinued.
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