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[ CAS No. 3335-98-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 3335-98-6
Chemical Structure| 3335-98-6
Chemical Structure| 3335-98-6
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Product Details of [ 3335-98-6 ]

CAS No. :3335-98-6 MDL No. :MFCD00234850
Formula : C14H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :OWPNVXATCSXTBK-UHFFFAOYSA-N
M.W : 209.24 Pubchem ID :314787
Synonyms :

Calculated chemistry of [ 3335-98-6 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 66.87
TPSA : 20.31 Ų

Pharmacokinetics

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) : -5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 2.51
Log Po/w (WLOGP) : 2.53
Log Po/w (MLOGP) : 2.88
Log Po/w (SILICOS-IT) : 2.86
Consensus Log Po/w : 2.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.21
Solubility : 0.13 mg/ml ; 0.00062 mol/l
Class : Soluble
Log S (Ali) : -2.58
Solubility : 0.547 mg/ml ; 0.00262 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.7
Solubility : 0.0042 mg/ml ; 0.0000201 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.87

Safety of [ 3335-98-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3335-98-6 ]

* 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.

  • Downstream synthetic route of [ 3335-98-6 ]

[ 3335-98-6 ] Synthesis Path-Downstream   1~64

  • 1
  • [ 3335-98-6 ]
  • [ 91-56-5 ]
  • (E)-1-phenyl-[3,3'-biindolinylidene]-2,2'-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With zirconium(IV) chloride; In ethanol;Reflux; General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.
  • 2
  • [ 5428-43-3 ]
  • [ 3335-98-6 ]
YieldReaction ConditionsOperation in experiment
60% With aluminum (III) chloride; In 1,2-dichloro-benzene; for 0.5h;Heating / reflux; Aluminum chloride (8.0 g, 60 mmol) is added in two portions to a solution of the above amide (5.0 g, 20.4 mmol) in 1,2-dichlorobenzene (10 mL). The reaction mixture is heated at reflux for 30 min, cooled slightly, poured onto ice (100 g) and the resulting solids are collected by filtration and washed with pentane. The resulting beige solid is dissolved in ethyl acetate, dried, filtered and concentrated to give 1-phenyl-1H-indol-2-one (2.53 g, 60% yield) as a beige solid. NMR 7.57 (2H, t), 7.41 (3H, m), 7.32 (1H, d), 7.2 (1H, t), 7.09 (1H, t), 6.79 (1H, d); 3.73 (2H, d).
  • 3
  • [ 3335-98-6 ]
  • [ 109-94-4 ]
  • 3-(Hydroxymethylene)-1-phenyloxindole [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; PREPARATION M7 1-Phenyl-3-(hydroxymethylene)-2(1H,2H)-indolone Potassium t-butoxide (1.63 g, 14.5 mmoles) and 5 ml absolute ethanol were heated to 80. 1-Phenyl-2(1H,3H)-indolone (2.09 g, 10 mmoles) was added, followed by ethyl formate (1.09 ml, 13.5 mmoles). The mixture was heated 5 minutes, cooled to 25, and the nearly solid mass diluted with 50 ml H2 O and crushed ice, acidified to pH 3 with 3N HCl and title product recovered by filtration, 2.2 g, m.p. 192-195; m/e 237. cf J. Prakt. Chem. 135:345-360 (1932); J. Med. Chem. 8:637 (1965).
  • 4
  • [ 723-89-7 ]
  • [ 3335-98-6 ]
YieldReaction ConditionsOperation in experiment
90% To a solution of commercially available 1-phenyl-1H-indole-2,3-dione (10.10 g, 45.7 mmol) in ethylene glycol (125 mL) is added powdered potassium hydroxide (7.4 g, 112 mmol), hydrazine hydrate (16.35 mL) and water (4 mL). The reaction is heated to 160 C. for 1.5 hr after which it is cooled to room temperature, made acidic with conc. hydrochloric acid, diluted with water and the resulting solids are collected by filtration. The solid is washed with water, dissolved in dichloromethane, dried and the solvent removed to give the 1-phenyl-1H-indol-2-one (8.6 g, 90% yield) as a solid.
With hydrazine hydrate; at 130℃; General procedure: Substituted isatin (10 mmol) was dissolved in hydrazine hydrate (98%, 10 mL, 32.5 mmol) and refluxed for 15-30 min (130 C). The reaction mixture was then poured into cold water, extracted withethyl acetate. The organic layer was then dried over sodium sulfate. Evaporation of the solvent and recrystallization from hexane/ethylacetate provided the substituted oxindole.
With hydrazine hydrate; for 1h;Reflux; General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2·NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.
  • 5
  • [ 3335-98-6 ]
  • [ 68-12-2 ]
  • [ 38367-40-7 ]
YieldReaction ConditionsOperation in experiment
With pyridine; trichlorophosphate; In dichloromethane; chloroform; at 5 - 20℃; for 48.5h; Phosphorous oxychloride (50 mL, 538 mmol) is added slowly to a solution of DMF (50 mL) in dichloromethane (50 mL) maintaining the temperature at 5 C. After 30 min, a solution of 1-phenyl-1H-indol-2-one (25 g, 120 mmol) and pyridine (25 mL, 309 mmol) in chloroform (125 mL) is added and the reaction is stirred 48 hr at room temperature. The reaction is poured into ice water (600 mL) and the aqueous layer is separated and extracted with chloroform (3×200 mL). The combined organic layer and extracts is dried, filtered and concentrated. The solid residue is crystallized from ethanol to afford 2-chloro-1-phenyl-1H-indole-3-carboxaldehyde (12.0 g, 39.25% yield) as an orange solid. NMR (CDCl3) 10.21 (1H, s), 8.37 (1H, d), 7.60 (3H, m), 7.41 (2H, m), 7.38 (1H, t), 7.28 (1H, m), 7.10 (1H, d). A second crop (7.5 g, 24.5% yield) is obtained by concentration of the filtrate and chromatography the residue eluting with dichloromethane.
  • 6
  • [ 71512-21-5 ]
  • [ 3335-98-6 ]
  • 7
  • [ 120230-90-2 ]
  • [ 3335-98-6 ]
  • 8
  • [ 5428-43-3 ]
  • [ 3335-98-6 ]
  • [ 519-87-9 ]
YieldReaction ConditionsOperation in experiment
1: 74% 2: 11% With tri-n-butyl-tin hydride In toluene for 14h; Heating;
  • 12
  • [ 3335-98-6 ]
  • [ 1016-78-0 ]
  • [ 1042159-67-0 ]
  • 13
  • [ 3335-98-6 ]
  • [ 334-22-5 ]
  • [ 1215121-49-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In N,N-dimethyl acetamide; mineral oil; benzene; at 50℃; Example 1Preparation of Compound 1 Sodium hydride (50% dispersion in mineral oil, 0.235 g, 4.8 mmol) was added to a stirred solution of <strong>[3335-98-6]1,3-dihydro-1-phenyl-2H-indol-2-one</strong> 1a (2.0 g, 9.6 mmol) in dimethylacetamide (25 mL). To the resulting solution was added bis(2-chloroethyl)amine (1.7 g, 9.6 mmol) in benzene (25 mL) at room temperature. The resulting reaction was heated to about 50 C. and allowed to stir at this temperature for 0.5 hours, then additional sodium hydride (0.235 g, 4.8 mmol) was added and stirring was continued for 2 hours. The reaction mixture was cooled to room temperature, diluted with benzene and treated with water. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to provide compound 1b.
  • 14
  • [ 3335-98-6 ]
  • [ 275-51-4 ]
  • [ 1365097-48-8 ]
YieldReaction ConditionsOperation in experiment
27% A typical procedure: Tf2O (203 mg, 0.72 mmol) in CH2Cl2 (5 mL) were added at room temperature to a solution of azulene (1) (67 mg, 0.52 mmol) and 2-indolinone (101 mg, 0.76 mmol) in CH2Cl2 (15 mL). The resulting solution was stirred at the same temperature for 2.5 hours. The reaction mixture was poured into a 2 M K2CO3 solution, extracted with AcOEt, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel with hexane/AcOEt (10:1) as an eluent to give 1-(indol-2-yl)azulene (2) (113 mg, 89%) as green crystals.
  • 16
  • [ 3335-98-6 ]
  • [ 358-23-6 ]
  • [ 1373936-46-9 ]
  • 17
  • [ 3335-98-6 ]
  • [ 104-55-2 ]
  • (E)-N-phenyl-3-(3'-phenylallylidene)-indolin-2-one [ No CAS ]
  • (Z)-N-phenyl-3-(3'-phenylallylidene)-indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With heptakis (6-O-triisopropylsilyl)-beta-cyclodextrin; 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 10℃; for 20h; General procedure: A mixture of oxindoles (2.0102 mmol), cinnamaldehyde,a base and a prescribed amount of TIPS-b-CDwas stirred in solvents(2 mL) at 10 C. After the removal of solvent in vacuo, the residuewas analyzed by 1H NMR to determine the reaction conversion andproduct distributions. The product was isolated by silica gel columnchromatography with a hexane/ethyl acetate (4:1, v/v) eluent. 4.5.12 (E)-N-Phenyl-3-(3'-phenylallylidene)-indolin-2-one ((E)-3g) Yellow prisms: mp 158-159 C, 1H NMR (DMSO-d6) delta 6.79 (d, J=7.7 Hz, 1H), 7.16 (dd, J=7.7, 7.7 Hz, 1H), 7.28 (dd, J=7.7, 7.7 Hz, 1H), 7.40-7.50 (m, 7H), 7.51 (s, 1H), 7.56-7.61 (m, 2H), 7.82-7.89 (m, 3H), 8.17 (d, J=7.7 Hz, 1H). 13C NMR (DMSO-d6) delta 109.0, 121.5, 122.7, 123.2, 124.2, 124.4, 126.9, 127.9, 128.3, 129.0, 129.2, 129.6, 130.0, 134.4, 135.8, 136.2, 142.8, 145.8, 166.9. IR: 1699.82 (C=O). HRMS (EI) m/z calcd for C23H17NO: 323.1310, found 323.1313.
  • 20
  • [ 3335-98-6 ]
  • [ 111-87-5 ]
  • [ 1571113-82-0 ]
  • 22
  • [ 3335-98-6 ]
  • [ 108-90-7 ]
  • [ 23210-25-5 ]
YieldReaction ConditionsOperation in experiment
95% With copper(II) ferrite; potassium carbonate; In 1,4-dioxane; at 70℃; for 1.33333h; General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.
  • 23
  • [ 3335-98-6 ]
  • [ 108-90-7 ]
  • [ 23210-25-5 ]
  • [ 124145-27-3 ]
YieldReaction ConditionsOperation in experiment
95%; 8% With cobalt ferrite; potassium carbonate; In 1,4-dioxane; at 70℃; for 4h; General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.
  • 24
  • [ 104-92-7 ]
  • [ 3335-98-6 ]
  • C21H17NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With copper(II) ferrite; potassium carbonate; In 1,4-dioxane; at 70℃; for 2h; General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.
  • 25
  • [ 3335-98-6 ]
  • [ 623-00-7 ]
  • C21H14N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With nickel(II) ferrite; potassium carbonate; In 1,4-dioxane; at 70℃; for 1.66667h; General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.
  • 26
  • [ 3335-98-6 ]
  • [ 623-00-7 ]
  • C21H14N2O [ No CAS ]
  • C28H17N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
88%; 7% With cobalt ferrite; potassium carbonate; In 1,4-dioxane; at 70℃; for 5h; General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.
  • 27
  • [ 3335-98-6 ]
  • [ 99-91-2 ]
  • C22H17NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With nickel(II) ferrite; potassium carbonate; In 1,4-dioxane; at 70℃; for 1.66667h; General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.
  • 28
  • [ 3335-98-6 ]
  • [ 99-91-2 ]
  • C22H17NO2 [ No CAS ]
  • C30H23NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87%; 6% With cobalt ferrite; potassium carbonate; In 1,4-dioxane; at 70℃; for 6h; General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.
  • 29
  • [ 3335-98-6 ]
  • [ 383-63-1 ]
  • (E)-1-phenyl-3-(2,2,2-trifluoro-1-hydroxyethylidene)indolin-2-one [ No CAS ]
  • 30
  • [ 3335-98-6 ]
  • 2-chloro-1-phenyl-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With trichlorophosphate; In dichloromethane; at 20℃; for 12h;Reflux; 1-phenyl-2,3-dihydro-1H-indol-2-oneTo 100 g (0.48 mol) was added to 1.5 L CH2Cl2. It was added to phosphoryl chloride 267 mL (2.87mol) at room temperature and heated to reflux for 12 hours. Slowly added dropwise to the ice-water cooling, the reaction solution and the reaction was terminated. The organic layer was extracted with CH2Cl2 and 2.0 L sat. Neutralized with aqueous NaHCO3 solution and washed with distilled water. The resulting organic layer was dried over anhydrous MgSO4, and evaporated under reduced pressure and purified by silica gel column chromatography to give the title compound 40.3 g (yield 37%):
  • 31
  • [ 2058-74-4 ]
  • [ 3335-98-6 ]
  • (E)-1-methyl-1'-phenyl-[3,3'-biindolinylidene]-2,2'-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With zirconium(IV) chloride; In ethanol;Reflux; General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.
  • 32
  • [ 3335-98-6 ]
  • [ 1217-89-6 ]
  • C29H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With zirconium(IV) chloride; In ethanol;Reflux; General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.
  • 33
  • [ 3335-98-6 ]
  • [ 41042-21-1 ]
  • (E)-ethyl 2-(2,2'-dioxo-1'-phenyl-[3,3'-biindolinylidene]-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With zirconium(IV) chloride; In ethanol;Reflux; General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.
  • 34
  • [ 3335-98-6 ]
  • [ 10487-31-7 ]
  • (E)-1-isopropyl-1'-phenyl-[3,3'-biindolinylidene]-2,2'-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With zirconium(IV) chloride; In ethanol;Reflux; General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.
  • 35
  • [ 3335-98-6 ]
  • [ 79183-44-1 ]
  • (E)-1-benzyl-5-bromo-1'-phenyl-[3,3'-biindolinylidene]-2,2'-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With zirconium(IV) chloride; In ethanol;Reflux; General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.
  • 36
  • [ 3335-98-6 ]
  • [ 332929-55-2 ]
  • (E)-5-bromo-1-butyl-1'-phenyl-[3,3'-biindolinylidene]-2,2'-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With zirconium(IV) chloride; In ethanol;Reflux; General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.
  • 37
  • [ 3335-98-6 ]
  • C16H20BrNO2 [ No CAS ]
  • (E)-5-bromo-1-(2-ethylhexyl)-1'-phenyl-[3,3'-biindolinylidene]-2,2'-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With zirconium(IV) chloride; In ethanol;Reflux; General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.
  • 38
  • [ 3335-98-6 ]
  • 4-methoxy-2-(trimethylsilyl)phenyl triflate [ No CAS ]
  • [ 121991-41-1 ]
  • 39
  • [ 3335-98-6 ]
  • [ 90-02-8 ]
  • C21H15NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With piperidine; In ethanol; at 90℃; General procedure: The reaction mixture of the substituted oxindole (1 equiv), the substituted salicylaldehyde (1.2 equiv) and piperidine (0.1 equiv) in ethanol (1-2 mL/1 mmol) was stirred at 90 C for 3-5 h. After the reaction mixture cooled down, the precipitate was filtered and washed with cold ethanol and diethyl ether, successively. Allowed to dry, the product was used in subsequent reaction without further purification.
  • 40
  • [ 3335-98-6 ]
  • 3-fluoro-1-phenylindolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: General Procedure: Under nitrogen atmosphere, to a stirred solution of N-substituted-2-oxindole (10 mmol) in dry Et2O (40 mL) was added LiHMDS (1.0 M in THF solution, 12 mmol, 12 mL) dropwise at 0 C. The solution was allowed to warm to ambient temperature and stirred for 1 h. Then the solution was cooled to 0 C and TMSCl (13 mmol, 1.6 mL) was added dropwise. The solution was allowed to warm to ambient temperature and stirred for another 3 h. The solvent was removed under reduced pressure, and dry MeCN (40 mL) was charged to the flask. The solution was cooled to 0 C again and Selectfluor (12 mmol, 4.3 g) was added to the solution in small portions. The resulting suspension was allowed to warm to ambient temperature and stirred overnight. The reaction was quenched by the addition of water (20 mL) and EtOAc (20 mL). The reaction mixture was extracted with EtOAc (20 mL × 2). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure Purification of the crude product was performed by flash column chromatography (Hexane/EtOAc) to afford 3-fluorooxindole.
  • 41
  • [ 3335-98-6 ]
  • [ 28150-90-5 ]
YieldReaction ConditionsOperation in experiment
89% With tert.-butylnitrite; In water; at 25℃; N-phenyl-2-indolone (1a, 0.3 mmol), t-butyl nitrite (t-BuONO, 2a, 1.2 mmol) and water (2 mL) were added to 10 mL of Schlenk vials and the reactor 25 C under stirring conditions, The reaction was monitored by TLC or GC until the reaction with N-phenyl-2-indolone was complete and the reaction was stopped. The reaction was diluted with ethyl acetate, The organic phase was dried over anhydrous sodium sulfate, filtered and distilled under reduced pressure. The residue was separated by column chromatography (n-hexane / ethyl acetate). The organic phase was extracted with ethyl acetate and the organic phase was separated. Ester) to give the desired product N-phenyl-isato-3-oxime I-3, yield 89%
  • 42
  • [ 3335-98-6 ]
  • [ 723-89-7 ]
YieldReaction ConditionsOperation in experiment
84% With tert.-butylhydroperoxide; In 1,2-dichloro-ethane; at 85℃; for 24h;Schlenk technique; General procedure: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time until complete consumption of starting material monitored by TLC analysis. After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).
80% With tert.-butylnitrite; oxygen; In tetrahydrofuran; at 50℃; under 760.051 Torr; for 24h;Schlenk technique; Inert atmosphere; General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.
66% With tert.-butylnitrite; In tetrahydrofuran; at 25℃; under 1520.1 Torr; To 10 ml schlenk bottle adding N - phenyl -2 - indolone (1 a, 0.3 mmol), tert-butyl nitrite (t - BuONO, 2 a, 0.6 mmol) and THF (2 ml), then oxygen atmosphere (1 atm) next, the reactor is placed 25 C stirring under the conditions of reaction, monitoring the reaction by TLC or GC process, to the reaction raw material N - phenyl -2 - indolone reaction is complete, to stop the reaction, the reaction the fluid uses full and salt water washing, recovering the organic phase, the aqueous phase is extracted with ethyl acetate, the combined organic phase; organic phase was dried with anhydrous sodium sulfate, filtered, distilled under reduced pressure, the residue by column chromatography (petroleum ether/ethyl acetate) separation to obtain the target product N - phenyl isatin, I - 4, the isolation yield is 66%
  • 43
  • [ 915378-36-8 ]
  • [ 3335-98-6 ]
  • 1',5-diphenyl-2,3-dihydrospiro[indene-4,3'-indoline]-2',7(1H)-dione [ No CAS ]
  • 44
  • [ 3335-98-6 ]
  • 1-(1-bromo-3,4-dihydronaphthalen-2-yl)-3-phenylprop-2-yn-1-one [ No CAS ]
  • 1,3'-diphenyl-9',10'-dihydro-1'H-spiro[indoline-3,4'-phenanthrene]-1',2-dione [ No CAS ]
  • 45
  • [ 3335-98-6 ]
  • 1-(2-bromocyclohept-1-en-1-yl)-3-phenylprop-2-yn-1-one [ No CAS ]
  • 1',2-diphenyl-6,7,8,9-tetrahydrospiro[benzo[7]annulene-1,3'-indoline]-2',4(5H)-dione [ No CAS ]
  • 46
  • [ 3335-98-6 ]
  • 1-bromo-1,5-diphenylpent-1-en-4-yn-3-one [ No CAS ]
  • 1',1',3'-triphenylspiro[cyclohexa[3',6']diene-2',3'-indoline]-2',5'-dione [ No CAS ]
  • 47
  • [ 3335-98-6 ]
  • [ 134419-77-5 ]
  • 1,2'-diphenyl-4'H-spiro[indoline-3,1'-naphthalene]-2,4'-dione [ No CAS ]
  • 48
  • [ 3335-98-6 ]
  • [ 1203669-21-9 ]
  • 2'-(4-methoxyphenyl)-1-phenyl-4'H-spiro[indoline-3,1'-naphthalene]-2,4'-dione [ No CAS ]
  • 49
  • [ 3335-98-6 ]
  • [ 1203669-20-8 ]
  • 2'-(4-ethylphenyl)-1-phenyl-4'H-spiro[indoline-3,1'-naphthalene]-2,4'-dione [ No CAS ]
  • 50
  • 1-(2-bromophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one [ No CAS ]
  • [ 3335-98-6 ]
  • 1-phenyl-2'-(3,4,5-trimethoxyphenyl)-4'H-spiro[indoline-3,1'-naphthalene]-2,4'-dione [ No CAS ]
  • 51
  • [ 16096-33-6 ]
  • [ 3335-98-6 ]
YieldReaction ConditionsOperation in experiment
62% With water; iodine; In N,N-dimethyl-formamide; for 12h;Reflux; 1 mmol of 1-phenylindole was added to a 10 mL round bottom flask, followed by 1 mL of N,N-dimethylformamide (DMF).2mL water and 0.5mmol elemental iodine (I2),The reaction was refluxed under air for 12 hours.After cooling, 10 mL of 10% Na2S2O3 was added to the reaction system.10 mL of saturated NaHCO3, extracted with 3×10 mL ethyl acetate.After drying anhydrous sodium sulfate, the solvent is recovered.Silica gel column chromatography gave 130 mg of a white solid.Yield 62%;
61% With 1-fluoro-1,2-phenyliodohydrin-3-(1H)-one; In 1,4-dioxane; water; at 140℃; for 5h; 0.4 mL of 1,4-dioxane was added to a 50 mL reaction tube at room temperature, and 2 mL of water was added thereto, and the mixture was stirred and mixed.Weighing 1-fluoro-1,2-phenyliodohydrin-3-(1H)-one (175 mg, 0.66 mmol) was added to the reaction tube and stirred for 1 min.After the reaction tube was placed in a 140 C oil bath,Was added N- phenyl-indole (116mg, 0.6mmol),A built-in condenser was added and reacted in a 140 C oil bath for 5 hours.The TLC dot plate showed that the raw material reaction was complete, and the reaction tube was taken out of the oil bath and cooled to room temperature.The reaction was quenched by the addition of 10 mL EtOAc.The organic layers were combined and dried over anhydrous sodium sulfate. The organic layer is concentrated by steaming,Separated by column chromatography to give a colorless solid N- phenyl-2-indolinone 76mg,The yield was 61%.
  • 52
  • [ 3335-98-6 ]
  • [ 265299-12-5 ]
  • methyl (E)-2-(2-oxo-1-phenylindolin-3-yl)methyl-3-(2-bromophenyl)prop-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% General procedure: To a precooled stirring suspension of NaH (6.0 mmol, 0.144 g) in THF (10 mL) at -78 C was added a solution of N-methyloxindole (5a) (6.0 mmol, 0.883 g) in THF (10 mL) dropwise. Then the cooling bath was removed and stirring continued for 5 min (till the formation of clear solution). Then the reaction mixture was again cooled to -78 C and a solution of methyl 3-hydroxy-2-methylene-3-phenylpropanoate (6a) (2.0 mmol, 0.468 g) in THF (15 mL) was added dropwise over 30 min. After stirring for further 10 min at the same temperature, the cooling bath was removed and the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (3×30 mL). Combined organic layer was dried over anhydrous Na2SO4.. Solvent was removed and the crude obtained was purified by column chromatography(10-15% EtOAc in hexanes) provided title compound (7a) (0.539 g) as a colorless solid in 84% yield.
  • 53
  • [ 3335-98-6 ]
  • [ 124957-36-4 ]
  • methyl (E)-2-(2-oxo-1-phenylindolin-3-yl)methyl-3-phenylprop-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% General procedure: To a precooled stirring suspension of NaH (6.0 mmol, 0.144 g) in THF (10 mL) at -78 C was added a solution of N-methyloxindole (5a) (6.0 mmol, 0.883 g) in THF (10 mL) dropwise. Then the cooling bath was removed and stirring continued for 5 min (till the formation of clear solution). Then the reaction mixture was again cooled to -78 C and a solution of methyl 3-hydroxy-2-methylene-3-phenylpropanoate (6a) (2.0 mmol, 0.468 g) in THF (15 mL) was added dropwise over 30 min. After stirring for further 10 min at the same temperature, the cooling bath was removed and the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (3×30 mL). Combined organic layer was dried over anhydrous Na2SO4.. Solvent was removed and the crude obtained was purified by column chromatography(10-15% EtOAc in hexanes) provided title compound (7a) (0.539 g) as a colorless solid in 84% yield.
  • 54
  • [ 3335-98-6 ]
  • [ 29179-25-7 ]
  • C31H25NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With caesium carbonate; In dichloromethane; at 20℃; for 0.666667h; General procedure: The mixture of 2,4-dien-1-one (0.5 mmol), indolin-2-one (0.5 mmol, 66.5 mg) and cesium carbonate (0.25 mmol, 81.3 mg) in 3 mL of methylene chloride was stirred at room temperature for 40 min. After the completion monitored by TLC, the solid was filtered, and the liquor was concentrated under reduced pressure. The residue was isolated by column chromatography using petroleum ether and ethyl acetate (v/v 3:1) as eluent to give the pure product. The analytical data for products are given in Tables 1 and 2.
  • 55
  • [ 108-86-1 ]
  • [ 3335-98-6 ]
  • [ 23210-25-5 ]
YieldReaction ConditionsOperation in experiment
85% With tris-(dibenzylideneacetone)dipalladium(0); C22H29O3P; potassium carbonate; In 1,4-dioxane; at 100℃; for 24h;Inert atmosphere; Sealed tube; General procedure: All reactions were conducted in 10 mL glass vials fitted with crimpcap septum caps. The reaction vial, equipped with a magnetic stir bar, was charged under an N2 atmosphere with the oxindole (2.25 mmol),Pd2(dba)3 (51 mg, 0.056 mmol, 2.5 mol%), i-Pr-BI-DIME (7) (41 mg,0.112 mmol, 5 mol%), K2CO3 (932 mg, 6.75 mmol) and the aryl bromide(1.1 equiv), then sealed with a crimp-cap septum. Dioxane (5.0 mL, degassed) was added via syringe and the reaction was stirred in an oil bath at 100 C for 24 h. The reaction mixture was then cooled to room temperature and filtered through a Celite pad using EtOAc (15mL) as eluent. The filtered solution was washed with H2O (5 mL),dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The crude residue was purified using a 12 g silica column(30% EtOAc/hexanes) to afford the desired oxindole product.
  • 56
  • 2-acetoxy-N,N-diphenylacetamide [ No CAS ]
  • [ 3335-98-6 ]
YieldReaction ConditionsOperation in experiment
84% With sulfuric acid; tetrabutylammomium bromide; In 5,5-dimethyl-1,3-cyclohexadiene; at 100℃; for 16h; 20 g of 2-acetoxy-N,N-diphenylacetamide (0.074 mol) was dissolved in 150 mL of xylene and added2.5 g of concentrated sulfuric acid (0.026 mol, 0.355 eq), 0.8 g of tetrabutylammonium bromide (0.0026 mol, 0.035 eq), the temperature was raised to 100 C, and the reaction was stirred for 16 hours. Drop to 25 ± 5 C, distill off the solvent under reduced pressure, add 200 mL of water, beat and filter. The solid was dried to give a white solid N-phenyl fluorenone.After recrystallization from ethanol, 12.9 g (yield 84%) was obtained. The structure identification results were similar to those of Example 7.
  • 57
  • [ 3335-98-6 ]
  • 3,3-diazido-1-phenylindolin-2-one [ No CAS ]
  • 58
  • [ 3335-98-6 ]
  • 6-methoxy-2-methylimidazo[2,1-b]thiazole-5-carbaldehyde [ No CAS ]
  • (E)-3-((6-methoxy-2-methylimidazo[2,1-b]thiazol-5-yl)methylene)-1-phenylindolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With piperidine; In methanol;Reflux; General procedure: The appropriate compound 2 (10 mmol) was dissolved inmethanol (100 mL) and treated with the equivalent of the appropriatealdehyde 1 and piperidine (1 mL). For compounds 39, 41 and42 the yield was much lower (5%), and an improvement (15-20%)was obtained by replacing piperidine with 33% NH4OHThe reaction mixture was refluxed for 5-10 h, except for compounds39-42 which required a longer reflux time (16-24 h; theprogress of the reaction was followed by TLC). The precipitate,formed on cooling, was collected by filtration.Compounds 39e41 were purified by column chromatographywith petroleum ether/acetone as the eluent. Most of the crudeproducts were crystallized from methanol, except 27 (acetone/petroleumether), 34, 43-48, 50-52 (ethanol) and 42, 49 (toluene). Inthe case of compound 10, the two E/Z isomers were isolated byfractional crystallization from methanol.
  • 59
  • [ 3335-98-6 ]
  • [ 109-94-4 ]
  • [ 3335-99-7 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In ethanol; at 80℃; for 0.0833333h; General procedure: A mixture of t-BuOK (1.63 g, 14.5 mmol) in EtOH (5.0 mL) was heated at 80 oC. Oxindole (10.0 mmol) was added, followed immediately by ethyl formate (1.09 mL, 13.5 mmol). Then, the reaction mixture was heated at 80 C for 5 min, and was cooled to 25 C. Crushed ice and H2O were added, then the mixture was acidified with 3 N HCl to pH = 3. The crude product was filtered and washed with water. Recrystallization from MeOH gave the pure product.
  • 60
  • [ 3335-98-6 ]
  • 1-benzyl-4-(pyrrolidin-1-yl)indoline-2,3-dione [ No CAS ]
  • 4-benzyl-1'-phenyl-4,5a,6a,7,8,9-hexahydro-5H-spiro[dipyrrolo[1,2-a :4',3',2'-de]quinoline-6,3'-in doline]-2',5-dione [ No CAS ]
  • 61
  • [ 3335-98-6 ]
  • [ 14369-81-4 ]
  • C26H27NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With triphenylphosphine; In 5,5-dimethyl-1,3-cyclohexadiene; at 50℃; for 24h;Inert atmosphere; General procedure: A mixture of oxindole 1 (0.30 mmol), allenoate 2 (0.75 mmol), PPh3 (0.045 mmol) in xylene (2.0 mL, dried over 4 A MS) was stirred at 50 C under Ar atmosphere for 24 h. After completion of the reaction (indicated by TLC), the mixture was quenched with saturated NaCl solution and diluted with EtOAc, followed by washing with H2O and saturated NaCl solution, and finally dried over Na2SO4. The crude product was purified by flash column chromatography to provide the corresponding product 3.
  • 63
  • [ 91-63-4 ]
  • [ 3335-98-6 ]
  • 3-hydroxy-1-phenyl-3-(quinolin-2-ylmethyl)indolin-2-one [ No CAS ]
  • 64
  • [ 79-55-0 ]
  • [ 3335-98-6 ]
  • [ 23210-22-2 ]
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