33333-60-7

Basic information

• Product Name: 3'-Hydroxy-1',3'-dihydro-1H,2'H-3,3'-biindol-2'-one
• Synonyms: 3'-Hydroxy-1',3'-dihydro-1H,2'H-3,3'-biindol-2'-one
• CAS NO: 33333-60-7
• Molecular Formula: C₁₆H₁₂N₂O₂
• Molecular Weight: 264.27868
• Mol File: 33333-60-7.mol
• Article Data: 29

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3'-Hydroxy-1',3'-dihydro-1H,2'H-3,3'-biindol-2'-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-Hydroxy-1',3'-dihydro-1H,2'H-3,3'-biindol-2'-one(33333-60-7)
• EPA Substance Registry System: 3'-Hydroxy-1',3'-dihydro-1H,2'H-3,3'-biindol-2'-one(33333-60-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 33333-60-7(Hazardous Substances Data)

Upstream product

• 120-72-9 indole 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 1454598-13-0 (2S)-(4-methoxybenzyloxy)-2-((3R)-2-oxo-3,3'-biindol-3-yl)acetaldehyde 
• 1454598-34-5 C₂₆H₂₄N₂O₄ 
• 1454598-26-5 (R)-3-((S)-2-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)ethyl)-3,3'-biindolin-2-one 
• 1454598-28-7 di-tert-butyl (3R)-3-((S)-2-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)ethyl)-2-oxo-3,3'-biindoline-1,1'-dicarboxylate 
• 1454598-29-8 di-tert-butyl (3R)-3-((S)-2-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)ethyl)-2-hydroxy-3,3'-biindoline-1,1'-dicarboxylate 
• 1454598-30-1 di-tert-butyl (3R)-3-((S)-2-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)ethyl)-2-hydroxy-3,3'-biindoline-1,1'-dicarboxylate 
• 1454598-31-2 di-tert-butyl (3R)-3-((S)-2-(tert-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)ethyl)-2-methoxy-3,3'-biindoline-1,1'-dicarboxylate 
• 1454598-37-8 C₃₆H₄₀N₂O₈ 
• 1454598-38-9 C₃₆H₄₂N₂O₈ 
• 1454598-39-0 tert-butyl 3a-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)-3-(4-methoxybenzyloxy)-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate 
• 1454598-12-9 C₂₅H₂₀N₂O₃ 

Relevant articles and documents

Supramolecular synthesis of 3-indolyl-3-hydroxy oxindoles under neutral conditions in water

(Chemical Equation Presented) Various 3-indolyl-3-hydroxy oxindoles were prepared for the first time by supramolecular catalysis involving the reaction of β-CD:isatin complexes with indoles under neutral conditions in water. β-Cyclodextrin can be recovered and reused a number of times without loss of activity.

Electro-organic synthesis of nanosized particles of 3-hydroxy-3-(1H-indol- 3-yl)indolin-2-one derivatives

This article describes an electrochemical method for preparation of nanosized particles of 3-hy-droxyoxindoles. The method is based on the reaction of isatins with indoles in propanol employing an undivided cell in the presence of NaBr as an electrolyte. The product was characterized after purification using infrared (IR), 1H nuclear magnetic resonance (NMR), 13C NMR, mass spectrometry (MS), and scanning electron microscopy (SEM).

-

-

Preparation, characterization, and catalysis application of nano-rods zinc oxide in the synthesis of 3-indolyl-3-hydroxy oxindoles in water

ZnO nano-rods is synthesized successfully by a new method employing Zn(OAc)2·2H2O, NH3 and polyethylene glycol (PEG, Mw = 2000). X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and BET surface area measurement were used to characterize the structure and morphology of the catalyst. Nano-rods ZnO has been found highly effective and recyclable catalyst for synthesis of 3-indolyl-3-hydroxy oxindole derivatives by Friedel-Crafts reaction of indole with isatins in excellent yields, in water.

An efficient Friedel-Crafts alkylation for the synthesis of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-diaryl oxindoles catalyzed by Dabco-based ionic liquids in water

A convenient and rapid method for the syntheses of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-diaryl oxindoles has been developed by using Dabco-based ionic liquid catalysts. The two ionic liquid catalysts, [Dabco-H][BF4] and [Dabco-H][HSO4] were found to be highly efficient catalysts for controlled 3-indolylation of isatins in water. When [Dabco-H][BF4] was employed as the catalyst in water at 55 °C, the reaction between isatins and indoles stops at the step of addition of the two components and afforded 3-indolyl-3-hydroxy oxindoles. While increasing the reaction temperature to 90 °C, the catalyst [Dabco-H][HSO4] could drive the reaction further and afford symmetrical 3,3-diindolyl oxindoles. By using the two kinds of ionic liquids, a two-step protocol for the efficient synthesis of unsymmetrical 3,3-diaryl oxindoles has also been developed. The use of water as the reaction medium makes the process environmentally benign. The catalysts can be recycled five times without activity loss.

Lambert Salt-Initiated Development of Friedel–Crafts Reaction on Isatin to Access Distinct Derivatives of Oxindoles

Herein, a mild metal-free and efficacious route for the synthesis of biologically important 3-aryl oxindole derivatives is described. Using Lambert salt-initiated hydroarylation of isatin, a diverse array of monoarylated products, symmetrical/unsymmetrical double-arylated products, and deoxygenated hydroarylated products could be synthesized from the single starting substrate in good to excellent yields. A preliminary mechanistic study revealed that the reaction proceeds via a monoarylated product followed by a nucleophilic attack by another electron-rich arene nucleophile under mild conditions. The potential of newly synthesized symmetric/unsymmetric 3,3-disubstituted oxindole, 3-substituted 3-hydroxy oxindoles, 3,3-di(indolyl)indolin-2-ones, and α-aryl oxindoles as valuable building blocks is further illustrated.

3-Hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one as a versatile intermediate for retro-Henry and Friedel-Crafts alkylation reactions in aqueous medium

The first example of a retro-Henry type reaction is reported using 3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-ones which are prepared via catalyst-free Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin. These compounds were used